Copper ferrite nanoparticles: an efficient catalyst for the one-pot four-component synthesis of pyrano[2,3-c] pyrazole derivatives

Copper ferrite nanoparticles: an efficient catalyst for the one-pot four-component synthesis of pyrano[2,3-c] pyrazole derivatives | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Copper ferrite nanoparticles: an efficient catalyst for the one-pot four-component synthesis of pyrano[2,3-c] pyrazole derivatives Amruta K. Mhaske, Anil G. Gadhave, Sachin V. Patil, Yogeshwar R. Baste, and 1 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-5877830/v1 This work is licensed under a CC BY 4.0 License Status: Posted Version 1 posted You are reading this latest preprint version Abstract An efficient CuFe 2 O 4 nonocatalyzed was synthesized by using triton X-100 as a surfactant in water. The synthesized catalyst was characterized by using FTIR, XRD, EDX, SEM and TEM techniques. The nanocatalyst successfully synthesized pyrano[2,3-c] pyrazoles derivatives through one-pot four-component condensation of aromatic aldehydes, malononitrile, ethyl acetoacetate and hydrazine hydrate in the presence of a catalytic amount of CuFe 2 O 4 as an efficient and inexpensive nanocatalyst. The yield of pyrano[2,3-c] pyrazoles was studied using various reaction parameters such as the amount of catalyst, type of solvent, reaction condition and time. This multicomponent reaction is simple, reduces toxicity, has a short reaction time and has a high product yield. All the synthesized pyrano[2,3-c] pyrazoles derivatives were characterized by IR, 1 H NMR, and 13 C NMR analysis. Additionally, the catalyst was reusable for up to four reaction runs. Copper ferrite nanoparticles pyrano[2 3-c] pyrazoles multi-component reaction water ethanol Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Introduction Spinel ferrite is a point of attraction to many researchers due to its shape, size, reusability, magnetic separation property [ 1 ] and unique crystal structure, affecting their chemical and physical properties [ 2 ]. It is able to maintain its chemical stability when exposed to various environmental conditions and change its physical features such as phase transitions, electrical switching, semiconducting, and magnetic properties [ 3 ]. Nanoscale materials magnetic properties are highly influenced by the size of crystalline solid regions known as crystallites due to both small size and surface effects. These modifications become more significant as particle size decreases [ 4 ]. Nanosized ferrites with uniform particle size and poor size distribution are suggested for a variety of applications, including focused medication administration, high-density recording media [ 5 ], gas sensing [ 6 , 7 ], ferrofluids [ 8 , 9 ], microwave devices [ 10 , 11 ], medical imaging, and other biological and pharmaceutical [ 12 ] applications such as hyperthermia [ 13 , 14 ], drug delivery [ 15 ] systems, and cancer therapy [ 16 , 17 ]. Ferrite has high electric resistance, flexibility, low eddy current losses, magnetoresistive, and magneto-optical properties, making it suitable for various power applications [ 18 ]. The advantages of ferrite nanoparticles include their capacity to functionalize a wide range of homogenous catalytically active reagents, including metals, as well as their chemical stability, rapid separation, and ability to create recyclable nanocatalysts [ 19 ]. In recent years, ferrite materials have been prepared using several techniques such as co-precipitation [ 20 – 22 ], hydrothermal [ 23 – 25 ], flash combustion, sol-gel [ 26 – 29 ], thermal decomposition [ 30 ], solvothermal [ 13 ], sonochemical [ 31 , 32 ], ceramic [ 5 , 33 ], ball milling [ 34 ], and microwave [ 35 ] synthesis. Among these sol-gel process has allowed good stoichiometric control over particle size and uniform distribution [ 36 ], economic and environmental benefits, including reduced time [ 37 ], high purity [ 37 ], early phase development, and recyclability with a low consumption of energy [ 2 ]. The sol-gel method is a cost-effective, useful, efficient, eco-friendly, and simple chemical process to create microscopic nanoparticles [ 38 , 39 ]. The current study, by using Triton X-100- assisted sol-gel method, is a law cost material, pure and simple, and the processor successfully synthesized CuFe 2 O 4 nanoparticles. In a multi-component reaction, three or more readily available components are put together in one pot in order to produce a final product that involves the characteristics of all the input reactants and as a result, provides many opportunities for molecular change in a single step with minimum efforts and time. Multi-component reaction of pyrano[2,3-c] pyrazoles are an important class of heterocyclic compounds that play an important role in the field of pharmaceutical chemistry in addition to being an essential tool for identifying life-saving drugs [ 40 ] biological function in medicinal and synthetic chemistry [ 41 , 42 ]. It contains different biological activities such as antibacterial [ 43 ], antifungal [ 44 ], insecticidal [ 42 ], antiviral [ 45 ], antimicrobial [ 44 ], antioxidant [ 46 ], anticoagulant [ 47 ], antipyretic [ 48 ], analgesic [ 49 ], anti-inflammatory [ 41 ], anticancer [ 50 , 41 ] and also serve as a potential inhibitor of human Chk1kinase [ 51 ] properties. They also provide potentially biodegradable agrochemicals, molluscicides, and some components that are commonly used as cosmetics and pigments [ 44 , 48 , 52 ]. Therefore, focus has been on developing innovative processes for the synthesis of pyrano[2,3-c] pyrazoles. Pyranopyrazoles were first developed in 1973 by reacting 3-methyl-1-phenylpyrazolin-5-one with tetracynoethylene [ 53 ]. In 1974, malononitrile was added to 4-arylidene-3-methyl-2-pyrazolin-5-one to create 2-amino-4-substituted pyrano[2,3-c] pyrazole-3-carbonitriles [ 48 ]. A number of strategies for the synthesis of these compounds have been reported, including one-pot three-component condensation of pyrazolone derivatives, malononitrile, and aromatic aldehydes [ 54 ], two-component reaction of 3-methyl-2-pyrazolin-5-one with benzylidene malononitriles [ 55 ], three-component cyclocondensation of substituted 4-piperidinones, 5-pyrazolones and malononitrile [ 56 ], four-component reaction of aromatic aldehydes, Meldrum’s acid, ethyl acetoacetate, with hydrazine hydrate [ 57 ]. Recently, pyrano[2,3-c] pyrazoles derivatives, including one-pot four-component condensation reactions of aromatic aldehydes, malononitrile, ethyl acetoacetate with hydrazine hydrate, have already synthesized with different catalysts, such as baker’s yeast [ 2 ], cetyltrimethylammonium chloride (CTACl) [ 58 ], molecular sieves 4Å [ 59 ], Aspergillus niger [ 60 ], dihydrogen 4, 4-trimethylenedipiperidine [H 2 -TMDP] [HPO 4 ] [ 47 ], TPGS-750-M/H 2 O [ 45 ], 1,3-dimethyl-2-oxo-1,3-bis(4-sulfobutyl) imidazolidine-1,3-dium hydrogen sulfate[DMDBSI].2HSO 4 [ 42 ], SBA/hydrotalcite/heteropoly acid (LDH/SBA/HPA) [ 43 ], aspirin [ 61 ], SiO 2 NPS [ 49 ], [bmim]OH [ 52 ], sodium benzoate [ 53 ], ZnO [ 40 ], nano CuI [ 62 ], tetraethylammonium bromide [ 63 ], γ-alumina [ 64 ], beta-CD (cyclodextrin) [ 51 ], MgFeCrO 4 [ 65 ], Ag/TiO 2 nano [ 66 ]. On the other hand, many of these procedures reported in the literature are associated with a number of limitations, including the use of hazardous solvents, harsh conditions, cost-effective reagents, long reaction time, and low yield products. Accordingly, there is strong demand for the development of a simple, efficient, environmentally friendly, and high-yield of products. In the persistence of our current research work [ 67 – 69 ], we report a new catalyst as CuFe 2 O 4 nanoparticles. This makes sense to support multi-step reactions for the synthesis of pyrano[2,3-c] pyrazoles derivatives through cyclocondensation reactions of aromatic aldehydes, malononitrile, and ethyl acetoacetate with hydrazine hydrate under reflux conditions. The current approach has several advantages, which include an ecologically benign reaction process, atom economy, easy workup, a short reaction time, and high-yield product. As a result, it is a simple approach for synthesizing organic chemicals and is now utilized to create heterocyclic compounds. Experimental Apparatus and Analysis The product was analyzed and compared to their physical, analytical, and spectral data previously reported in the literature. FT-IR spectra of the catalyst CuFe 2 O 4 nanoparticles were recorded at room temperature in the range of 400–4000 cm − l by a Perkin Elmer spectrum. The BRUKER instrument was used to determine the elemental composition of the nanocatalyst while analyzing the EDX spectrum. with an XPERT-pro diffractometer using CuK α radiation, the structural properties of the materials were determined using X-ray diffraction (XRD) of the nanocatalyst. The melting points of all compounds have been measured using an open capillary tube. Thin-layer chromatography that utilizes silica-gel coated ALUGRAM SIL G UV254 plates was observed under UV light. The 1 H NMR and 13 C NMR spectra were recorded on a Bruker Avance NEO 500 MHz and 125 MHz spectrometer using TMS as a reference and DMSO as a solvent. Preparation of copper ferrite nanoparticles The chemical compounds used in the synthesis of copper ferrite nanoparticles are ferric nitrate, copper nitrate, ammonia, citric acid, and Triton X-100 as surfactant. In a typical synthesis, 4.18 g of ferric nitrate and 1.87 g of copper nitrate were dissolved in 80 ml of deionized water to obtain a nitrate solution, followed by the addition of 2 g of citric acid under constant stirring. An aqueous solution of Triton X-100 was mixed with the nitrate solution. The required amount of ammonia is added into the solution to maintain the 7 pH. The mixed solution was placed in a heating magnetic stirrer continuously at 90 o C. Then the solution is evaporating and turns into a very thick gel. Then the gel is heated at 120 o C for 6 h, respectively. Finally, the synthesized product was calcinized at 850 o C for 3 h, and crystallized copper ferrite nanoparticles were obtained. General Procedure for Synthesis of pyrano [2, 3-c] pyrazoles derivatives In a round-bottom flask, a mixture of aromatic aldehyde (1 mmol), malononitrile (1 mmol), ethyl acetoacetate (1 mmol), and hydrazine hydrate (1 mmol) in the presence of copper ferrite (0.05 g) as a catalyst was refluxed in ethanol and water (9:1) as a solvent. The progress of the reaction was monitored by thin-layer chromatography (n-hexane: ethyl acetate 4:1) analysis. After completion of the reaction, the reaction mass was cooled, filtered off, and washed with distilled water. The residue was dissolved in hot ethanol and then subjected to simple filtration until the undissolved catalyst was separated from the reaction mixture by simple filtration. The filtrate was allowed to evaporate at room temperature, resulting in a pure product. Spectral Data 6-Amino-2, 4-dihydro-3-methyl-4-phenylpyrano [2,3-c] pyrazole-5-carbonitrile (5a): White solid, Mp-244-246 o C, IR (KBr) υ max = 3371, 3165, 2191, 1645, 1595, 1487, 1452, 1400, 1224, 1161 cm − l . 1 H NMR (500 MHz, DMSO, δppm): 1.789 (s, 3H, CH 3 ), 4.59 (s, 1H, CH), 6.86 (s, 2H, NH 2 ), 7.16–7.33 (m, 5H, Ar-H), 12.10 (s, 1H, NH). 13 C NMR (125 MHz, DMSO, δppm): 160.77, 154.67, 144.34, 136.46, 128.32, 127.36, 126.62, 120.67, 97.54, 57.11, 36.14, 9.62. 6-amino-4-(4-chlorophenyl)-3-methyl-1,4-dihydropyranol [2,3-c] pyrazole-5-carbonitrile (5b): Yellow solid, Mp-236-238 o C, IR (KBr) υ max = 2362, 2191, 1645, 1593, 1439, 1394, 1203 cm − l . 1 H NMR (500 MHz, DMSO, δppm): 1.80 (s, 3H, CH 3 ), 4.63 (s, 1H, CH), 6.90 (s, 2H, NH 2 ), 7.19–7.21 (d, J = 8.4 Hz, 2H, Ar-H), 7.37–7.39 (d, J = 8.4 Hz, 2H, Ar-H), 12.17 (s, 1H, NH). 13 C NMR (125 MHz, DMSO, δppm): 160.79, 154.58, 143.37, 135.55, 131.10, 129.91 129.24, 128.98, 128.33, 120.51, 97.07, 56.65, 35.45, 9.62. 6-amino-4-(4-methoxyphenyl)-3-methyl-1,4-dihydropyranol [2,3-c] pyrazole-5-carbonitrile (5k): Yellow solid, Mp-212-214 o C, IR (KBr) υ max = 2191, 1635, 1595, 1492, 1386, 1298, 1257, 1170 cm − l . 1 H NMR (500 MHz, DMSO, δppm): 1.79 (s, 3H, CH 3 ), 3.73 (s, 3H, CH 3 ), 4.55 (S, 1H,CH), 6.80 (s, 2H, NH 2 ) 6.87–6.89 (d, J = 8.6 Hz, 2H, Ar-H), 7.08–7.10 (d, J = 8.6 Hz, 2H, Ar-H), 12.11 (s, 1H, NH). 13 C NMR (125 MHz, DMSO, δppm): 160.57, 157.85, 154.64, 136.38, 135.44, 128.38, 120.72, 113.65, 97.77, 57.52, 54.88, 35.34, 9.64. Results and Discussion Catalyst Characterization Fourier Transform Infrared (FT-IR) Spectroscopy Fourier transform infrared spectra of copper ferrite nanoparticles (Fig. 1 ). The spinal ferrite lattice metal ion vibration corresponds to the FTIR absorption bands. The spinel ferrite is indicative of two different bands corresponding to tetrahedral and octahedral sites that are observed around 400 cm − l and 600 cm − l . The higher frequency range corresponds to the fundamental stretching vibration of the tetrahedral sites, where the lower frequency range corresponds to the fundamental stretching vibration of the octahedral sites [ 8 ]. Presently, the observed stretching vibration of Fe-O (Fig. 1 ) at clearly indicating a strong absorption band at 540 cm − l was attributed to the tetrahedral sites of copper ferrite. Moreover, the absorption peak at 434 cm − l indicates the presence of a Cu-O stretching vibration, which corresponds to octahedral sites of copper ferrite [ 12 , 13 ]. X-ray Photoelectron Spectroscopy The crystallized copper ferrite nanoparticles were performed by XRD, and powder diffraction patterns were presented in (Fig. 2 ). The diffraction pattern of copper ferrite can match with the body-centered cubic (BCC) structure of copper ferrite, according to peak positions of the standard JCPDS card no. (PDF#34–0425). The peaks appeared at 2θ range of 18.3, 30.1, 34.8, 35.9, 37.1, 43.8, 57.1, 62.1, 63.5, 66.1, and 74.7 which corresponds to the reflection planes (101), (200), (103), (211), (202), (220), (303), (224), (400), (323), (413), respectively [ 18 ]. The most intense XRD peak is at 35.9, corresponding to the (211) plane. The crystalline size of copper ferrite was calculated with the help of the full width at half maximum (FWHM) of XRD peaks by using the Debye-Scherrer equation [ 3 ]. $$\:D=\frac{K\lambda\:}{\beta\:{cos}\theta\:}$$ Where K = Scherrer’s constant and the value is 0.9 in aspherical form, D = average crystalline size (Å), \(\:\lambda\:\) = wavelength of the incident X-ray beam (1.54 Å), B = full width at half maxima in radians [FWHM], θ = Bragg’s diffraction angle. It was found that the average crystallite size of copper ferrite was around 18.44 nm, respectively [ 2 ]. Energy-Dispersive X-ray Spectroscopy (EDX) Analysis The chemical composition of copper ferrite spinel ferrite is determined by EDX analysis. The elemental composition of copper ferrite nanoparticles is shown in (Fig. 3 ). It shows the presence of Cu, Fe, and O elements. It concluded that no other elements were present in the sample, which means that the prepared sample is pure. The atomic percentages of Cu, Fe, and O were found at 37%, 26%, and 36% respectively. Scanning Electron Microscopy (SEM) Analysis The morphology was observed using scanning electron microscopy images of prepared samples of copper ferrite nanoparticles are shown in (Fig. 4 ). The copper ferrite morphology was produced using the sol-gel auto-combust on process at 750 nm in a 15 K magnification scale SEM picture of the response. SEM spectrum can provide surface morphology, The grain morphology, size, consistency, and distribution have all been observed. but EDX analyzes the chemical structure and purity of copper ferrite nanoparticles. copper ferrite nanoparticles showed that larger shapes with irregular and nonuniform distribution due to their network-like structure been formed. Transmission electron microscope (TEM) analysis The crystalline spinel structure of copper ferrite nanoparticles can be seen by the corresponding selected area of electron diffraction (SAED) patterns of all diffraction spots that are identified as spherical shapes, as shown in (Fig. 4 ). The copper ferrite nanoparticles show the strongest scattered patterns, indicating a highly crystalline spinel structure with a narrow size distribution. The SAED pattern supports the reflection planes (101), (200), (103), (211), (202), (220), (303), (224), (400), (323), and (413) observed in the XRD pattern. The copper ferrite nanoparticles average crystalline size was about 18.44 nm and supported by the XRD pattern. Application of copper ferrite nanoparticles for synthesis of pyrano [2, 3-c] pyrazoles derivatives In this work, copper ferrite nanoparticles were prepared and used for the one-pot synthesis of pyrano [2, 3-c] pyrazole derivatives using substituted aromatic aldehyde, malononitrile, ethyl acetoacetate, and hydrazine hydrate (Scheme. 1). To check the catalytic activity of copper ferrite nanoparticles was studied to give one-pot synthesis of pyrano [2, 3-c] pyrazoles derivatives. The effect of reaction conditions, solvent, temperature, and time are optimized as shown in (Table 1). The model reaction was carried out in different reaction conditions like solvent-free, ultrasonic, stirring, and reflux conditions. It is concluded that the reaction was conducted in a solvent-free and ultrasonication does not yield a product yield and stirring reaction conditions at used different solvent does produce sufficient product yield. Then the model reaction was carried out under reflux conditions. All of these solvents, EtOH:H 2 O (9:1), was selected as the solvent system for this transformation at various solvents such as EtOH, H 2 O, EtOH:H 2 O (1:1), and EtOH:H 2 O (9:1). According to this, EtOH:H 2 O (9:1) is a more suitable reflux condition for the successful synthesis of pyrano[2,3-c]pyrazoles. This resulted in a greater yield and a shorter reaction time. Table.1 Optimization of different reaction conditions for the synthesis of pyranopyrazole derivatives Entry Condition Temp ( o C) Time (min) Yield (%) 1 Solvent-free 100–110 40 No reaction 2 Ultrasonic irradiation -- 60 No reaction 3 H 2 O: EtOH, Stirring RT 1h No reaction 4 EtOH, Stirring RT 1h 22 5 H 2 O Stirring 60–80 4h 32 6 EtOH Reflux 2h 36 7 H 2 O Reflux 2h 42 8 EtOH:H 2 O (1:1) Reflux 2h 66 10 EtOH:H 2 O (9:1) Reflux 2h 96 11 EtOH:H 2 O (9:1) Reflux 1h 96 12 EtOH:H 2 O (9:1) Reflux 30 82 Reaction condition: aromatic aldehyde (1 mmol), malononitrile (1 mmol), ethyl aceto acetate (1 mmol), hydrazine hydrate (1 mmol) and CuFe 2 O 4 NPs When determining the effectiveness of copper ferrite nanoparticles as a catalyst for the synthesis of pyrano [2, 3-c] pyrazoles and optimizing the reaction conditions, we studied benzaldehyde, malononitrile, ethyl acetoacetate, and hydrazine hydrate as a model reaction. The reaction proceeds in the absence of catalyst, reaction is not observed with a longer reaction time. It was observed that as the amount of catalyst is increased, the product yield also increases. The best result was obtained for 50 mg of CuFe 2 O 4 nanoparticles to obtain a 96% of yield within 60 min. (Table 2 ) Table 2 Optimization of different amount of catalyst loading studies in the synthesis of pyranopyrazole derivatives Entry Amount of catalyst (mg) Reaction time (min) Yield (%) 1 0 120 0 2 10 100 46 3 20 60 64 4 30 60 78 5 40 60 89 6 50 60 96 7 60 60 96 Reaction condition: aromatic aldehyde (1 mmol), malononitrile (1 mmol), ethyl aceto acetate (1 mmol), hydrazine hydrate (1 mmol) and CuFe 2 O 4 NPs under reflux condition After the optimization of the reaction conditions, a number of substituted aromatic aldehydes were successfully treated with malononitrile, ethyl acetoacetate, and hydrazine hydrate, and the results were summarized in (Table 3 ). Following the reaction, a wide range of aromatic aldehydes with either electron-donating and electron-withdrawing groups such as the ortho, meta, and para substituents, successfully worked to produce the respective products in high yield within a short reaction time. In addition, the steric effect had an impact on this reaction. In this case, since 2-nitrobezaldehyde (4f) sterically hindered in the ortho position substituted by the nitro group, it required a longer reaction time than 4-nitrobenzaldehyde (4c) and 2-chlorobenzaldehyde (4e), which are sterically hindered in the ortho position, and it required a longer reaction time than 4-chlorobenzaldehyde (4b). Thus, we determined that the functional groups electromagnetic nature and their different positions on aromatic aldehydes affect this reaction in different ways. We studied the use of different substrates to react with the hydrazine hydrate, ethyl acetoacetate, and malononitrile, resulting in the production of pyrano [2, 3-c] pyrazole derivatives (4a-m). Table. 3: Synthesis of pyranopyrazolone in the presence of CuFe 2 O 4 NPs as catalyst in EtOH:H 2 O (9:1) under reflux condition To synthesize of pyrano[2,3-c] pyrazoles, the catalytic efficiency of copper ferrite nanoparticles has been compared with many other reported catalysts (Table 4 ). The reaction of benzaldehyde was selected as the model reaction, and its temperature, time of reaction, amount of catalyst, and percentage yield were examined and compared. This present work is better than reported work. Table 4 Comparison of present work for synthesis of pyranopyrazole with literature reported different catalytic systems Entry Catalyst Solvent Temp ( o C) Time (Hr) Yield (%) References 1 Bakers yeast EtOH RT, Stirring 34 88 48 2 Bakers yeast EtOH RT, Stirring 34 78 58 3 CTACI H 2 O 90, Stirred 4 89 59 4 MS EtOH Reflux 1 84 60 5 ANL EtOH 60, Stirring 1 90 61 6 CuFe 2 O 4 NPs EtOH: H 2 O (9:1) Reflux 1 96 Present work Plausible Mechanism The pyrano[2,3-c] pyrazole derivatives synthesis is a conventionally base-catalyzed reaction that cannot occur in the absence of base. The possible method for using copper ferrite nanoparticles to synthesize pyrano[2,3-c] pyrazole derivatives appears in (Fig. 6 ). The most acidic proton from malononitrile to the copper ferrite nanoparticles acts as a base and subsequently creates the Knoevenagel product. In the next step the condensation of hydrazine hydrate and ethyl acetoacetate, which then combined with molecular sieves to make enol. The reaction, which further involves the Michael type addition with the Knoevenagel product. The intermediate is generated from the condensation of intermolecular cyclization to generate the pyrano[2,3-c] pyrazole derivatives. Reusability of the Catalyst In optimum conditions, the reusability and recovery of copper ferrite nanoparticles have been studied in the synthesis of pyrano[2,3-c] pyrazoles through the condensation of benzaldehyde, malononitrile, ethyl acetoacetate, and hydrazine hydrate. After the completion of the reaction, the recovered catalyst is extracted with distilled water. The catalyst could be recovered after water was removed under low pressure and dried at 30 o C for 1 h after complete drying. Which was reused four times without losing its catalytic activity. Conclusion In the present research, by using newly prepared copper ferrite nanoparticles, was successfully demonstration of one pot four component reaction for the synthesis of pyrano[2,3-c] pyrazoles derivatives was achieved. The optimized results show it is easy, has a short reaction time of 60 min, a high yield of 96% and a catalyst amount of 0.05 g using ethanol: water in reflux conditions. The reusability of the catalyst makes it very desirable, and separation techniques make this synthesis process highly advantageous. Declarations Competing Interest The authors declare no claim of interest, economic or in any other way. Author Contribution Amruta K. Mhaske-Contribute the table workAnil G. Gadhave-Contribute the analysis of NMR, MS spectraSachin V. Patil-Contribute the analysisYogeshwar R. Baste-Contribute the XRD analysisBhagwat K. Uphade-Contribute the design the methods and monitoring the work Acknowledgement The authors are thankful to the Management and principal, P. V. P. 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Uphade, Synthesis of tetrahydro-benzo[a]xanthene-11-ones by indium sulfide nano-particles as green an efficient and reusable catalyst under solvent-free condition. J. Sulfur Chem. 45 (4), 459–476 (2024) Tables Table 3 is available in the Supplementary Files section. Additional Declarations No competing interests reported. Supplementary Files Table3.docx floatimage1.png Graphical Abstract Cite Share Download PDF Status: Posted Version 1 posted You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-5877830","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":405631793,"identity":"831b56a1-2508-4073-8de6-81b335620f08","order_by":0,"name":"Amruta K. 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copper ferrite nanoparticles\u003c/p\u003e","description":"","filename":"image2.png","url":"https://assets-eu.researchsquare.com/files/rs-5877830/v1/c504d40af567e12bb8c5b023.png"},{"id":74665656,"identity":"04e3fcb4-34c8-45f9-a56b-59b76039899b","added_by":"auto","created_at":"2025-01-24 13:16:02","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":150369,"visible":true,"origin":"","legend":"\u003cp\u003eEDX spectra of copper ferrite nanoparticles\u003c/p\u003e","description":"","filename":"image3.png","url":"https://assets-eu.researchsquare.com/files/rs-5877830/v1/aecf34da7adbf886371274d9.png"},{"id":74665661,"identity":"988dde2f-c4ea-4642-bd51-3e481e1a663a","added_by":"auto","created_at":"2025-01-24 13:16:03","extension":"jpeg","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":88957,"visible":true,"origin":"","legend":"\u003cp\u003eSEM image of copper ferrite nanoparticles\u003c/p\u003e","description":"","filename":"image4.jpeg","url":"https://assets-eu.researchsquare.com/files/rs-5877830/v1/4a0297ccbe9f68759e8663f1.jpeg"},{"id":74665664,"identity":"e7d94cdc-e733-4ceb-b7bd-40939e21400d","added_by":"auto","created_at":"2025-01-24 13:16:03","extension":"jpeg","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":88519,"visible":true,"origin":"","legend":"\u003cp\u003eTEM and SAED image of copper ferrite nanoparticles\u003c/p\u003e","description":"","filename":"image5.jpeg","url":"https://assets-eu.researchsquare.com/files/rs-5877830/v1/13ca7031010626a1913dcb5b.jpeg"},{"id":74665652,"identity":"602d1650-1a65-4d98-b2eb-05b57aa01e7d","added_by":"auto","created_at":"2025-01-24 13:16:02","extension":"png","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":41482,"visible":true,"origin":"","legend":"\u003cp\u003ePlausible mechanisms for synthesis of pyrano[2,3-c] pyrazoles\u003c/p\u003e","description":"","filename":"image6.png","url":"https://assets-eu.researchsquare.com/files/rs-5877830/v1/3644e08fea66a5aa994b3e2d.png"},{"id":74666897,"identity":"e08d1cd5-0c78-4742-baf4-9da462b873aa","added_by":"auto","created_at":"2025-01-24 13:24:03","extension":"png","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":53339,"visible":true,"origin":"","legend":"\u003cp\u003eReusability of CuFe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e NPs for synthesis of 6-amino-2, 4-dihydro-3-methyl-4-phenylpyrano [2,3-c] pyrazole-5-carbonitrile as model reaction\u003c/p\u003e","description":"","filename":"image7.png","url":"https://assets-eu.researchsquare.com/files/rs-5877830/v1/c7ca4006320a15fe7c409b74.png"},{"id":74932432,"identity":"87a5eb77-f5f2-43f3-b29c-d3191d6d1edb","added_by":"auto","created_at":"2025-01-28 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class=\"CitationRef\"\u003e2\u003c/span\u003e]. It is able to maintain its chemical stability when exposed to various environmental conditions and change its physical features such as phase transitions, electrical switching, semiconducting, and magnetic properties [\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e]. Nanoscale materials magnetic properties are highly influenced by the size of crystalline solid regions known as crystallites due to both small size and surface effects. These modifications become more significant as particle size decreases [\u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e4\u003c/span\u003e]. Nanosized ferrites with uniform particle size and poor size distribution are suggested for a variety of applications, including focused medication administration, high-density recording media [\u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e], gas sensing [\u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e, \u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e], ferrofluids [\u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e, \u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e9\u003c/span\u003e], microwave devices [\u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e10\u003c/span\u003e, \u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e], medical imaging, and other biological and pharmaceutical [\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e] applications such as hyperthermia [\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e, \u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e], drug delivery [\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e] systems, and cancer therapy [\u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e16\u003c/span\u003e, \u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e17\u003c/span\u003e]. Ferrite has high electric resistance, flexibility, low eddy current losses, magnetoresistive, and magneto-optical properties, making it suitable for various power applications [\u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e]. The advantages of ferrite nanoparticles include their capacity to functionalize a wide range of homogenous catalytically active reagents, including metals, as well as their chemical stability, rapid separation, and ability to create recyclable nanocatalysts [\u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eIn recent years, ferrite materials have been prepared using several techniques such as co-precipitation [\u003cspan additionalcitationids=\"CR21\" citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR22\" class=\"CitationRef\"\u003e22\u003c/span\u003e], hydrothermal [\u003cspan additionalcitationids=\"CR24\" citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e25\u003c/span\u003e], flash combustion, sol-gel [\u003cspan additionalcitationids=\"CR27 CR28\" citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR29\" class=\"CitationRef\"\u003e29\u003c/span\u003e], thermal decomposition [\u003cspan citationid=\"CR30\" class=\"CitationRef\"\u003e30\u003c/span\u003e], solvothermal [\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e], sonochemical [\u003cspan citationid=\"CR31\" class=\"CitationRef\"\u003e31\u003c/span\u003e, \u003cspan citationid=\"CR32\" class=\"CitationRef\"\u003e32\u003c/span\u003e], ceramic [\u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e, \u003cspan citationid=\"CR33\" class=\"CitationRef\"\u003e33\u003c/span\u003e], ball milling [\u003cspan citationid=\"CR34\" class=\"CitationRef\"\u003e34\u003c/span\u003e], and microwave [\u003cspan citationid=\"CR35\" class=\"CitationRef\"\u003e35\u003c/span\u003e] synthesis. Among these sol-gel process has allowed good stoichiometric control over particle size and uniform distribution [\u003cspan citationid=\"CR36\" class=\"CitationRef\"\u003e36\u003c/span\u003e], economic and environmental benefits, including reduced time [\u003cspan citationid=\"CR37\" class=\"CitationRef\"\u003e37\u003c/span\u003e], high purity [\u003cspan citationid=\"CR37\" class=\"CitationRef\"\u003e37\u003c/span\u003e], early phase development, and recyclability with a low consumption of energy [\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e]. The sol-gel method is a cost-effective, useful, efficient, eco-friendly, and simple chemical process to create microscopic nanoparticles [\u003cspan citationid=\"CR38\" class=\"CitationRef\"\u003e38\u003c/span\u003e, \u003cspan citationid=\"CR39\" class=\"CitationRef\"\u003e39\u003c/span\u003e]. The current study, by using Triton X-100- assisted sol-gel method, is a law cost material, pure and simple, and the processor successfully synthesized CuFe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e nanoparticles.\u003c/p\u003e \u003cp\u003eIn a multi-component reaction, three or more readily available components are put together in one pot in order to produce a final product that involves the characteristics of all the input reactants and as a result, provides many opportunities for molecular change in a single step with minimum efforts and time. Multi-component reaction of pyrano[2,3-c] pyrazoles are an important class of heterocyclic compounds that play an important role in the field of pharmaceutical chemistry in addition to being an essential tool for identifying life-saving drugs [\u003cspan citationid=\"CR40\" class=\"CitationRef\"\u003e40\u003c/span\u003e] biological function in medicinal and synthetic chemistry [\u003cspan citationid=\"CR41\" class=\"CitationRef\"\u003e41\u003c/span\u003e, \u003cspan citationid=\"CR42\" class=\"CitationRef\"\u003e42\u003c/span\u003e]. It contains different biological activities such as antibacterial [\u003cspan citationid=\"CR43\" class=\"CitationRef\"\u003e43\u003c/span\u003e], antifungal [\u003cspan citationid=\"CR44\" class=\"CitationRef\"\u003e44\u003c/span\u003e], insecticidal [\u003cspan citationid=\"CR42\" class=\"CitationRef\"\u003e42\u003c/span\u003e], antiviral [\u003cspan citationid=\"CR45\" class=\"CitationRef\"\u003e45\u003c/span\u003e], antimicrobial [\u003cspan citationid=\"CR44\" class=\"CitationRef\"\u003e44\u003c/span\u003e], antioxidant [\u003cspan citationid=\"CR46\" class=\"CitationRef\"\u003e46\u003c/span\u003e], anticoagulant [\u003cspan citationid=\"CR47\" class=\"CitationRef\"\u003e47\u003c/span\u003e], antipyretic [\u003cspan citationid=\"CR48\" class=\"CitationRef\"\u003e48\u003c/span\u003e], analgesic [\u003cspan citationid=\"CR49\" class=\"CitationRef\"\u003e49\u003c/span\u003e], anti-inflammatory [\u003cspan citationid=\"CR41\" class=\"CitationRef\"\u003e41\u003c/span\u003e], anticancer [\u003cspan citationid=\"CR50\" class=\"CitationRef\"\u003e50\u003c/span\u003e, \u003cspan citationid=\"CR41\" class=\"CitationRef\"\u003e41\u003c/span\u003e] and also serve as a potential inhibitor of human Chk1kinase [\u003cspan citationid=\"CR51\" class=\"CitationRef\"\u003e51\u003c/span\u003e] properties. They also provide potentially biodegradable agrochemicals, molluscicides, and some components that are commonly used as cosmetics and pigments [\u003cspan citationid=\"CR44\" class=\"CitationRef\"\u003e44\u003c/span\u003e, \u003cspan citationid=\"CR48\" class=\"CitationRef\"\u003e48\u003c/span\u003e, \u003cspan citationid=\"CR52\" class=\"CitationRef\"\u003e52\u003c/span\u003e]. Therefore, focus has been on developing innovative processes for the synthesis of pyrano[2,3-c] pyrazoles.\u003c/p\u003e \u003cp\u003ePyranopyrazoles were first developed in 1973 by reacting 3-methyl-1-phenylpyrazolin-5-one with tetracynoethylene [\u003cspan citationid=\"CR53\" class=\"CitationRef\"\u003e53\u003c/span\u003e]. In 1974, malononitrile was added to 4-arylidene-3-methyl-2-pyrazolin-5-one to create 2-amino-4-substituted pyrano[2,3-c] pyrazole-3-carbonitriles [\u003cspan citationid=\"CR48\" class=\"CitationRef\"\u003e48\u003c/span\u003e]. A number of strategies for the synthesis of these compounds have been reported, including one-pot three-component condensation of pyrazolone derivatives, malononitrile, and aromatic aldehydes [\u003cspan citationid=\"CR54\" class=\"CitationRef\"\u003e54\u003c/span\u003e], two-component reaction of 3-methyl-2-pyrazolin-5-one with benzylidene malononitriles [\u003cspan citationid=\"CR55\" class=\"CitationRef\"\u003e55\u003c/span\u003e], three-component cyclocondensation of substituted 4-piperidinones, 5-pyrazolones and malononitrile [\u003cspan citationid=\"CR56\" class=\"CitationRef\"\u003e56\u003c/span\u003e], four-component reaction of aromatic aldehydes, Meldrum\u0026rsquo;s acid, ethyl acetoacetate, with hydrazine hydrate [\u003cspan citationid=\"CR57\" class=\"CitationRef\"\u003e57\u003c/span\u003e]. Recently, pyrano[2,3-c] pyrazoles derivatives, including one-pot four-component condensation reactions of aromatic aldehydes, malononitrile, ethyl acetoacetate with hydrazine hydrate, have already synthesized with different catalysts, such as baker\u0026rsquo;s yeast [\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e], cetyltrimethylammonium chloride (CTACl) [\u003cspan citationid=\"CR58\" class=\"CitationRef\"\u003e58\u003c/span\u003e], molecular sieves 4\u0026Aring; [\u003cspan citationid=\"CR59\" class=\"CitationRef\"\u003e59\u003c/span\u003e], Aspergillus niger [\u003cspan citationid=\"CR60\" class=\"CitationRef\"\u003e60\u003c/span\u003e], dihydrogen 4, 4-trimethylenedipiperidine [H\u003csub\u003e2\u003c/sub\u003e-TMDP] [HPO\u003csub\u003e4\u003c/sub\u003e] [\u003cspan citationid=\"CR47\" class=\"CitationRef\"\u003e47\u003c/span\u003e], TPGS-750-M/H\u003csub\u003e2\u003c/sub\u003eO [\u003cspan citationid=\"CR45\" class=\"CitationRef\"\u003e45\u003c/span\u003e], 1,3-dimethyl-2-oxo-1,3-bis(4-sulfobutyl) imidazolidine-1,3-dium hydrogen sulfate[DMDBSI].2HSO\u003csub\u003e4\u003c/sub\u003e [\u003cspan citationid=\"CR42\" class=\"CitationRef\"\u003e42\u003c/span\u003e], SBA/hydrotalcite/heteropoly acid (LDH/SBA/HPA) [\u003cspan citationid=\"CR43\" class=\"CitationRef\"\u003e43\u003c/span\u003e], aspirin [\u003cspan citationid=\"CR61\" class=\"CitationRef\"\u003e61\u003c/span\u003e], SiO\u003csub\u003e2\u003c/sub\u003e NPS [\u003cspan citationid=\"CR49\" class=\"CitationRef\"\u003e49\u003c/span\u003e], [bmim]OH [\u003cspan citationid=\"CR52\" class=\"CitationRef\"\u003e52\u003c/span\u003e], sodium benzoate [\u003cspan citationid=\"CR53\" class=\"CitationRef\"\u003e53\u003c/span\u003e], ZnO [\u003cspan citationid=\"CR40\" class=\"CitationRef\"\u003e40\u003c/span\u003e], nano CuI [\u003cspan citationid=\"CR62\" class=\"CitationRef\"\u003e62\u003c/span\u003e], tetraethylammonium bromide [\u003cspan citationid=\"CR63\" class=\"CitationRef\"\u003e63\u003c/span\u003e], γ-alumina [\u003cspan citationid=\"CR64\" class=\"CitationRef\"\u003e64\u003c/span\u003e], beta-CD (cyclodextrin) [\u003cspan citationid=\"CR51\" class=\"CitationRef\"\u003e51\u003c/span\u003e], MgFeCrO\u003csub\u003e4\u003c/sub\u003e [\u003cspan citationid=\"CR65\" class=\"CitationRef\"\u003e65\u003c/span\u003e], Ag/TiO\u003csub\u003e2\u003c/sub\u003e nano [\u003cspan citationid=\"CR66\" class=\"CitationRef\"\u003e66\u003c/span\u003e]. On the other hand, many of these procedures reported in the literature are associated with a number of limitations, including the use of hazardous solvents, harsh conditions, cost-effective reagents, long reaction time, and low yield products. Accordingly, there is strong demand for the development of a simple, efficient, environmentally friendly, and high-yield of products.\u003c/p\u003e \u003cp\u003eIn the persistence of our current research work [\u003cspan additionalcitationids=\"CR68\" citationid=\"CR67\" class=\"CitationRef\"\u003e67\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR69\" class=\"CitationRef\"\u003e69\u003c/span\u003e], we report a new catalyst as CuFe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e nanoparticles. This makes sense to support multi-step reactions for the synthesis of pyrano[2,3-c] pyrazoles derivatives through cyclocondensation reactions of aromatic aldehydes, malononitrile, and ethyl acetoacetate with hydrazine hydrate under reflux conditions. The current approach has several advantages, which include an ecologically benign reaction process, atom economy, easy workup, a short reaction time, and high-yield product. As a result, it is a simple approach for synthesizing organic chemicals and is now utilized to create heterocyclic compounds.\u003c/p\u003e"},{"header":"Experimental","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003eApparatus and Analysis\u003c/h2\u003e \u003cp\u003eThe product was analyzed and compared to their physical, analytical, and spectral data previously reported in the literature. FT-IR spectra of the catalyst CuFe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e nanoparticles were recorded at room temperature in the range of 400\u0026ndash;4000 cm\u003csup\u003e\u0026minus;\u0026thinsp;l\u003c/sup\u003e by a Perkin Elmer spectrum. The BRUKER instrument was used to determine the elemental composition of the nanocatalyst while analyzing the EDX spectrum. with an XPERT-pro diffractometer using CuK\u003csub\u003eα\u003c/sub\u003e radiation, the structural properties of the materials were determined using X-ray diffraction (XRD) of the nanocatalyst. The melting points of all compounds have been measured using an open capillary tube. Thin-layer chromatography that utilizes silica-gel coated ALUGRAM SIL G UV254 plates was observed under UV light. The \u003csup\u003e1\u003c/sup\u003eH NMR and \u003csup\u003e13\u003c/sup\u003eC NMR spectra were recorded on a Bruker Avance NEO 500 MHz and 125 MHz spectrometer using TMS as a reference and DMSO as a solvent.\u003c/p\u003e \u003c/div\u003e\n\u003ch3\u003ePreparation of copper ferrite nanoparticles\u003c/h3\u003e\n\u003cp\u003eThe chemical compounds used in the synthesis of copper ferrite nanoparticles are ferric nitrate, copper nitrate, ammonia, citric acid, and Triton X-100 as surfactant. In a typical synthesis, 4.18 g of ferric nitrate and 1.87 g of copper nitrate were dissolved in 80 ml of deionized water to obtain a nitrate solution, followed by the addition of 2 g of citric acid under constant stirring. An aqueous solution of Triton X-100 was mixed with the nitrate solution. The required amount of ammonia is added into the solution to maintain the 7 pH. The mixed solution was placed in a heating magnetic stirrer continuously at 90\u003csup\u003eo\u003c/sup\u003eC. Then the solution is evaporating and turns into a very thick gel. Then the gel is heated at 120\u003csup\u003eo\u003c/sup\u003eC for 6 h, respectively. Finally, the synthesized product was calcinized at 850\u003csup\u003eo\u003c/sup\u003eC for 3 h, and crystallized copper ferrite nanoparticles were obtained.\u003c/p\u003e\n\u003ch3\u003eGeneral Procedure for Synthesis of pyrano [2, 3-c] pyrazoles derivatives\u003c/h3\u003e\n\u003cp\u003eIn a round-bottom flask, a mixture of aromatic aldehyde (1 mmol), malononitrile (1 mmol), ethyl acetoacetate (1 mmol), and hydrazine hydrate (1 mmol) in the presence of copper ferrite (0.05 g) as a catalyst was refluxed in ethanol and water (9:1) as a solvent. The progress of the reaction was monitored by thin-layer chromatography (n-hexane: ethyl acetate 4:1) analysis. After completion of the reaction, the reaction mass was cooled, filtered off, and washed with distilled water. The residue was dissolved in hot ethanol and then subjected to simple filtration until the undissolved catalyst was separated from the reaction mixture by simple filtration. The filtrate was allowed to evaporate at room temperature, resulting in a pure product.\u003c/p\u003e \u003cp\u003e\u003cimg src=\"https://myfiles.space/user_files/127393_c7e80a1c9bb65875/127393_custom_files/img1737723491.png\"\u003e\u003cbr\u003e\u003c/p\u003e\n\u003ch3\u003eSpectral Data\u003c/h3\u003e\n\u003cdiv id=\"Sec7\" class=\"Section2\"\u003e \u003ch2\u003e6-Amino-2, 4-dihydro-3-methyl-4-phenylpyrano [2,3-c] pyrazole-5-carbonitrile (5a):\u003c/h2\u003e \u003cp\u003eWhite solid, Mp-244-246\u003csup\u003eo\u003c/sup\u003eC, IR (KBr) υ\u003csub\u003emax\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;3371, 3165, 2191, 1645, 1595, 1487, 1452, 1400, 1224, 1161 cm\u003csup\u003e\u0026minus;\u0026thinsp;l\u003c/sup\u003e. \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO, δppm): 1.789 (s, 3H, CH\u003csub\u003e3\u003c/sub\u003e), 4.59 (s, 1H, CH), 6.86 (s, 2H, NH\u003csub\u003e2\u003c/sub\u003e), 7.16\u0026ndash;7.33 (m, 5H, Ar-H), 12.10 (s, 1H, NH). \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO, δppm): 160.77, 154.67, 144.34, 136.46, 128.32, 127.36, 126.62, 120.67, 97.54, 57.11, 36.14, 9.62.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec8\" class=\"Section2\"\u003e \u003ch2\u003e6-amino-4-(4-chlorophenyl)-3-methyl-1,4-dihydropyranol [2,3-c] pyrazole-5-carbonitrile (5b):\u003c/h2\u003e \u003cp\u003eYellow solid, Mp-236-238\u003csup\u003eo\u003c/sup\u003eC, IR (KBr) υ\u003csub\u003emax\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;2362, 2191, 1645, 1593, 1439, 1394, 1203 cm\u003csup\u003e\u0026minus;\u0026thinsp;l\u003c/sup\u003e. \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO, δppm): 1.80 (s, 3H, CH\u003csub\u003e3\u003c/sub\u003e), 4.63 (s, 1H, CH), 6.90 (s, 2H, NH\u003csub\u003e2\u003c/sub\u003e), 7.19\u0026ndash;7.21 (d, J\u0026thinsp;=\u0026thinsp;8.4 Hz, 2H, Ar-H), 7.37\u0026ndash;7.39 (d, J\u0026thinsp;=\u0026thinsp;8.4 Hz, 2H, Ar-H), 12.17 (s, 1H, NH). \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO, δppm): 160.79, 154.58, 143.37, 135.55, 131.10, 129.91 129.24, 128.98, 128.33, 120.51, 97.07, 56.65, 35.45, 9.62.\u003c/p\u003e \u003c/div\u003e\n\u003ch3\u003e6-amino-4-(4-methoxyphenyl)-3-methyl-1,4-dihydropyranol [2,3-c] pyrazole-5-carbonitrile (5k):\u003c/h3\u003e\n\u003cp\u003eYellow solid, Mp-212-214\u003csup\u003eo\u003c/sup\u003eC, IR (KBr) υ\u003csub\u003emax\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;2191, 1635, 1595, 1492, 1386, 1298, 1257, 1170 cm\u003csup\u003e\u0026minus;\u0026thinsp;l\u003c/sup\u003e. \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO, δppm): 1.79 (s, 3H, CH\u003csub\u003e3\u003c/sub\u003e), 3.73 (s, 3H, CH\u003csub\u003e3\u003c/sub\u003e), 4.55 (S, 1H,CH), 6.80 (s, 2H, NH\u003csub\u003e2\u003c/sub\u003e) 6.87\u0026ndash;6.89 (d, J\u0026thinsp;=\u0026thinsp;8.6 Hz, 2H, Ar-H), 7.08\u0026ndash;7.10 (d, J\u0026thinsp;=\u0026thinsp;8.6 Hz, 2H, Ar-H), 12.11 (s, 1H, NH). \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO, δppm): 160.57, 157.85, 154.64, 136.38, 135.44, 128.38, 120.72, 113.65, 97.77, 57.52, 54.88, 35.34, 9.64.\u003c/p\u003e"},{"header":"Results and Discussion","content":"\u003cdiv id=\"Sec11\" class=\"Section2\"\u003e\n \u003ch2\u003eCatalyst Characterization\u003c/h2\u003e\n \u003cdiv id=\"Sec12\" class=\"Section3\"\u003e\n \u003ch2\u003eFourier Transform Infrared (FT-IR) Spectroscopy\u003c/h2\u003e\n \u003cp\u003eFourier transform infrared spectra of copper ferrite nanoparticles (Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e). The spinal ferrite lattice metal ion vibration corresponds to the FTIR absorption bands. The spinel ferrite is indicative of two different bands corresponding to tetrahedral and octahedral sites that are observed around 400 cm\u003csup\u003e\u0026minus;\u0026thinsp;l\u003c/sup\u003e and 600 cm\u003csup\u003e\u0026minus;\u0026thinsp;l\u003c/sup\u003e. The higher frequency range corresponds to the fundamental stretching vibration of the tetrahedral sites, where the lower frequency range corresponds to the fundamental stretching vibration of the octahedral sites [\u003cspan class=\"CitationRef\"\u003e8\u003c/span\u003e]. Presently, the observed stretching vibration of Fe-O (Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e) at clearly indicating a strong absorption band at 540 cm\u003csup\u003e\u0026minus;\u0026thinsp;l\u003c/sup\u003e was attributed to the tetrahedral sites of copper ferrite. Moreover, the absorption peak at 434 cm\u003csup\u003e\u0026minus;\u0026thinsp;l\u003c/sup\u003e indicates the presence of a Cu-O stretching vibration, which corresponds to octahedral sites of copper ferrite [\u003cspan class=\"CitationRef\"\u003e12\u003c/span\u003e, \u003cspan class=\"CitationRef\"\u003e13\u003c/span\u003e].\u003c/p\u003e\n \u003c/div\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec13\" class=\"Section2\"\u003e\n \u003ch2\u003eX-ray Photoelectron Spectroscopy\u003c/h2\u003e\n \u003cp\u003eThe crystallized copper ferrite nanoparticles were performed by XRD, and powder diffraction patterns were presented in (Fig. \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e). The diffraction pattern of copper ferrite can match with the body-centered cubic (BCC) structure of copper ferrite, according to peak positions of the standard JCPDS card no. (PDF#34\u0026ndash;0425). The peaks appeared at 2\u0026theta; range of 18.3, 30.1, 34.8, 35.9, 37.1, 43.8, 57.1, 62.1, 63.5, 66.1, and 74.7 which corresponds to the reflection planes (101), (200), (103), (211), (202), (220), (303), (224), (400), (323), (413), respectively [\u003cspan class=\"CitationRef\"\u003e18\u003c/span\u003e].\u003c/p\u003e\n \u003cp\u003eThe most intense XRD peak is at 35.9, corresponding to the (211) plane. The crystalline size of copper ferrite was calculated with the help of the full width at half maximum (FWHM) of XRD peaks by using the Debye-Scherrer equation [\u003cspan class=\"CitationRef\"\u003e3\u003c/span\u003e].\u003c/p\u003e\n \u003cdiv id=\"Equa\" class=\"Equation\"\u003e\n \u003cdiv class=\"mathdisplay\" id=\"FileID_Equa\" name=\"EquationSource\"\u003e$$\\:D=\\frac{K\\lambda\\:}{\\beta\\:{cos}\\theta\\:}$$\u003c/div\u003e\n \u003c/div\u003e\n \u003cp\u003eWhere K\u0026thinsp;=\u0026thinsp;Scherrer\u0026rsquo;s constant and the value is 0.9 in aspherical form, D\u0026thinsp;=\u0026thinsp;average crystalline size (\u0026Aring;), \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\:\\lambda\\:\\)\u003c/span\u003e\u003c/span\u003e = wavelength of the incident X-ray beam (1.54 \u0026Aring;), B\u0026thinsp;=\u0026thinsp;full width at half maxima in radians [FWHM], \u0026theta;\u0026thinsp;=\u0026thinsp;Bragg\u0026rsquo;s diffraction angle. It was found that the average crystallite size of copper ferrite was around 18.44 nm, respectively [\u003cspan class=\"CitationRef\"\u003e2\u003c/span\u003e].\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec14\" class=\"Section2\"\u003e\n \u003ch2\u003eEnergy-Dispersive X-ray Spectroscopy (EDX) Analysis\u003c/h2\u003e\n \u003cp\u003eThe chemical composition of copper ferrite spinel ferrite is determined by EDX analysis. The elemental composition of copper ferrite nanoparticles is shown in (Fig. \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e). It shows the presence of Cu, Fe, and O elements. It concluded that no other elements were present in the sample, which means that the prepared sample is pure. The atomic percentages of Cu, Fe, and O were found at 37%, 26%, and 36% respectively.\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec15\" class=\"Section2\"\u003e\n \u003ch2\u003eScanning Electron Microscopy (SEM) Analysis\u003c/h2\u003e\n \u003cp\u003eThe morphology was observed using scanning electron microscopy images of prepared samples of copper ferrite nanoparticles are shown in (Fig. \u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e). The copper ferrite morphology was produced using the sol-gel auto-combust on process at 750 nm in a 15 K magnification scale SEM picture of the response. SEM spectrum can provide surface morphology, The grain morphology, size, consistency, and distribution have all been observed. but EDX analyzes the chemical structure and purity of copper ferrite nanoparticles. copper ferrite nanoparticles showed that larger shapes with irregular and nonuniform distribution due to their network-like structure been formed.\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec16\" class=\"Section2\"\u003e\n \u003ch2\u003eTransmission electron microscope (TEM) analysis\u003c/h2\u003e\n \u003cp\u003eThe crystalline spinel structure of copper ferrite nanoparticles can be seen by the corresponding selected area of electron diffraction (SAED) patterns of all diffraction spots that are identified as spherical shapes, as shown in (Fig. \u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e). The copper ferrite nanoparticles show the strongest scattered patterns, indicating a highly crystalline spinel structure with a narrow size distribution. The SAED pattern supports the reflection planes (101), (200), (103), (211), (202), (220), (303), (224), (400), (323), and (413) observed in the XRD pattern. The copper ferrite nanoparticles average crystalline size was about 18.44 nm and supported by the XRD pattern.\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec17\" class=\"Section2\"\u003e\n \u003ch2\u003eApplication of copper ferrite nanoparticles for synthesis of pyrano [2, 3-c] pyrazoles derivatives\u003c/h2\u003e\n \u003cp\u003eIn this work, copper ferrite nanoparticles were prepared and used for the one-pot synthesis of pyrano [2, 3-c] pyrazole derivatives using substituted aromatic aldehyde, malononitrile, ethyl acetoacetate, and hydrazine hydrate (Scheme. 1).\u003c/p\u003e\n \u003cp\u003eTo check the catalytic activity of copper ferrite nanoparticles was studied to give one-pot synthesis of pyrano [2, 3-c] pyrazoles derivatives. The effect of reaction conditions, solvent, temperature, and time are optimized as shown in (Table\u0026nbsp;1). The model reaction was carried out in different reaction conditions like solvent-free, ultrasonic, stirring, and reflux conditions. It is concluded that the reaction was conducted in a solvent-free and ultrasonication does not yield a product yield and stirring reaction conditions at used different solvent does produce sufficient product yield. Then the model reaction was carried out under reflux conditions. All of these solvents, EtOH:H\u003csub\u003e2\u003c/sub\u003eO (9:1), was selected as the solvent system for this transformation at various solvents such as EtOH, H\u003csub\u003e2\u003c/sub\u003eO, EtOH:H\u003csub\u003e2\u003c/sub\u003eO (1:1), and EtOH:H\u003csub\u003e2\u003c/sub\u003eO (9:1). According to this, EtOH:H\u003csub\u003e2\u003c/sub\u003eO (9:1) is a more suitable reflux condition for the successful synthesis of pyrano[2,3-c]pyrazoles. This resulted in a greater yield and a shorter reaction time.\u003c/p\u003e\n \u003cp\u003e\u003cstrong\u003eTable.1\u0026nbsp;\u003c/strong\u003eOptimization of different reaction conditions for the synthesis of pyranopyrazole derivatives\u003c/p\u003e\n \u003cdiv class=\"gridtable\"\u003e\n \u003ctable id=\"Taba\" border=\"1\"\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eEntry\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eCondition\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eTemp (\u003csup\u003eo\u003c/sup\u003eC)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eTime (min)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eYield (%)\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSolvent-free\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u0026ndash;110\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e40\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eNo reaction\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eUltrasonic irradiation\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e--\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e60\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eNo reaction\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eH\u003csub\u003e2\u003c/sub\u003eO: EtOH, Stirring\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eRT\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1h\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eNo reaction\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEtOH, Stirring\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eRT\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1h\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e22\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eH\u003csub\u003e2\u003c/sub\u003eO Stirring\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e60\u0026ndash;80\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4h\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e32\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEtOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eReflux\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2h\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e36\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eH\u003csub\u003e2\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eReflux\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2h\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e42\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEtOH:H\u003csub\u003e2\u003c/sub\u003eO (1:1)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eReflux\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2h\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e66\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEtOH:H\u003csub\u003e2\u003c/sub\u003eO (9:1)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eReflux\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2h\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e96\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e11\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEtOH:H\u003csub\u003e2\u003c/sub\u003eO (9:1)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eReflux\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1h\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e96\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEtOH:H\u003csub\u003e2\u003c/sub\u003eO (9:1)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eReflux\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e82\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003ctfoot\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"5\"\u003eReaction condition: aromatic aldehyde (1 mmol), malononitrile (1 mmol), ethyl aceto acetate (1 mmol), hydrazine hydrate (1 mmol) and CuFe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e NPs\u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tfoot\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n \u003cp\u003eWhen determining the effectiveness of copper ferrite nanoparticles as a catalyst for the synthesis of pyrano [2, 3-c] pyrazoles and optimizing the reaction conditions, we studied benzaldehyde, malononitrile, ethyl acetoacetate, and hydrazine hydrate as a model reaction. The reaction proceeds in the absence of catalyst, reaction is not observed with a longer reaction time. It was observed that as the amount of catalyst is increased, the product yield also increases. The best result was obtained for 50 mg of CuFe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e nanoparticles to obtain a 96% of yield within 60 min. (Table \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e)\u0026nbsp;\u003c/p\u003e\n \u003ctable id=\"Tab1\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv class=\"CaptionNumber\"\u003eTable 2\u003c/div\u003e\n \u003cdiv class=\"CaptionContent\"\u003e\n \u003cp\u003eOptimization of different amount of catalyst loading studies in the synthesis of pyranopyrazole derivatives\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eEntry\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eAmount of catalyst (mg)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eReaction time (min)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eYield (%)\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e46\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e60\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e64\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e60\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e78\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e40\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e60\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e89\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e6\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e\u003cstrong\u003e50\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e\u003cstrong\u003e60\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e\u003cstrong\u003e96\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e60\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e60\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e96\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003ctfoot\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"4\"\u003eReaction condition: aromatic aldehyde (1 mmol), malononitrile (1 mmol), ethyl aceto acetate (1 mmol), hydrazine hydrate (1 mmol) and CuFe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003eNPs under reflux condition\u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tfoot\u003e\n \u003c/table\u003e\n \u003cp\u003e\u003c/p\u003e\n \u003cp\u003eAfter the optimization of the reaction conditions, a number of substituted aromatic aldehydes were successfully treated with malononitrile, ethyl acetoacetate, and hydrazine hydrate, and the results were summarized in (Table \u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e). Following the reaction, a wide range of aromatic aldehydes with either electron-donating and electron-withdrawing groups such as the ortho, meta, and para substituents, successfully worked to produce the respective products in high yield within a short reaction time. In addition, the steric effect had an impact on this reaction. In this case, since 2-nitrobezaldehyde (4f) sterically hindered in the ortho position substituted by the nitro group, it required a longer reaction time than 4-nitrobenzaldehyde (4c) and 2-chlorobenzaldehyde (4e), which are sterically hindered in the ortho position, and it required a longer reaction time than 4-chlorobenzaldehyde (4b). Thus, we determined that the functional groups electromagnetic nature and their different positions on aromatic aldehydes affect this reaction in different ways. We studied the use of different substrates to react with the hydrazine hydrate, ethyl acetoacetate, and malononitrile, resulting in the production of pyrano [2, 3-c] pyrazole derivatives (4a-m).\u003c/p\u003e\n \u003cp\u003e\u003cstrong\u003eTable. 3:\u0026nbsp;\u003c/strong\u003eSynthesis of pyranopyrazolone in the presence of CuFe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e4\u0026nbsp;\u003c/sub\u003eNPs as catalyst in EtOH:H\u003csub\u003e2\u003c/sub\u003eO (9:1) under reflux condition\u003c/p\u003e\n \u003cp\u003eTo synthesize of pyrano[2,3-c] pyrazoles, the catalytic efficiency of copper ferrite nanoparticles has been compared with many other reported catalysts (Table \u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e). The reaction of benzaldehyde was selected as the model reaction, and its temperature, time of reaction, amount of catalyst, and percentage yield were examined and compared. This present work is better than reported work.\u003c/p\u003e\n \u003ctable id=\"Tab3\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv class=\"CaptionNumber\"\u003eTable 4\u003c/div\u003e\n \u003cdiv class=\"CaptionContent\"\u003e\n \u003cp\u003eComparison of present work for synthesis of pyranopyrazole with literature reported different catalytic systems\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eEntry\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eCatalyst\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eSolvent\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eTemp (\u003csup\u003eo\u003c/sup\u003eC)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eTime (Hr)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eYield (%)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eReferences\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eBakers yeast\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEtOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eRT, Stirring\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e34\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e88\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e48\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eBakers yeast\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEtOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eRT, Stirring\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e34\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e78\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e58\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCTACI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eH\u003csub\u003e2\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e90, Stirred\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e89\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e59\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eMS\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEtOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eReflux\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e84\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e60\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eANL\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEtOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e60, Stirring\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e61\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e6\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eCuFe\u003c/strong\u003e\u003csub\u003e\u003cstrong\u003e2\u003c/strong\u003e\u003c/sub\u003e\u003cstrong\u003eO\u003c/strong\u003e\u003csub\u003e\u003cstrong\u003e4\u003c/strong\u003e\u003c/sub\u003e \u003cstrong\u003eNPs\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eEtOH: H\u003c/strong\u003e\u003csub\u003e\u003cstrong\u003e2\u003c/strong\u003e\u003c/sub\u003e\u003cstrong\u003eO (9:1)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eReflux\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e\u003cstrong\u003e1\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e\u003cstrong\u003e96\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003ePresent work\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n \u003cp\u003e\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec18\" class=\"Section2\"\u003e\n \u003ch2\u003ePlausible Mechanism\u003c/h2\u003e\n \u003cp\u003eThe pyrano[2,3-c] pyrazole derivatives synthesis is a conventionally base-catalyzed reaction that cannot occur in the absence of base. The possible method for using copper ferrite nanoparticles to synthesize pyrano[2,3-c] pyrazole derivatives appears in (Fig. \u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003e). The most acidic proton from malononitrile to the copper ferrite nanoparticles acts as a base and subsequently creates the Knoevenagel product. In the next step the condensation of hydrazine hydrate and ethyl acetoacetate, which then combined with molecular sieves to make enol. The reaction, which further involves the Michael type addition with the Knoevenagel product. The intermediate is generated from the condensation of intermolecular cyclization to generate the pyrano[2,3-c] pyrazole derivatives.\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec19\" class=\"Section2\"\u003e\n \u003ch2\u003eReusability of the Catalyst\u003c/h2\u003e\n \u003cp\u003eIn optimum conditions, the reusability and recovery of copper ferrite nanoparticles have been studied in the synthesis of pyrano[2,3-c] pyrazoles through the condensation of benzaldehyde, malononitrile, ethyl acetoacetate, and hydrazine hydrate. After the completion of the reaction, the recovered catalyst is extracted with distilled water. The catalyst could be recovered after water was removed under low pressure and dried at 30\u003csup\u003eo\u003c/sup\u003eC for 1 h after complete drying. Which was reused four times without losing its catalytic activity.\u003c/p\u003e\n\u003c/div\u003e"},{"header":"Conclusion","content":"\u003cp\u003eIn the present research, by using newly prepared copper ferrite nanoparticles, was successfully demonstration of one pot four component reaction for the synthesis of pyrano[2,3-c] pyrazoles derivatives was achieved. The optimized results show it is easy, has a short reaction time of 60 min, a high yield of 96% and a catalyst amount of 0.05 g using ethanol: water in reflux conditions. The reusability of the catalyst makes it very desirable, and separation techniques make this synthesis process highly advantageous.\u003c/p\u003e"},{"header":"Declarations","content":" \u003ch2\u003eCompeting Interest\u003c/h2\u003e \u003cp\u003eThe authors declare no claim of interest, economic or in any other way.\u003c/p\u003e\u003ch2\u003eAuthor Contribution\u003c/h2\u003e\u003cp\u003eAmruta K. Mhaske-Contribute the table workAnil G. Gadhave-Contribute the analysis of NMR, MS spectraSachin V. Patil-Contribute the analysisYogeshwar R. Baste-Contribute the XRD analysisBhagwat K. Uphade-Contribute the design the methods and monitoring the work\u003c/p\u003e\u003ch2\u003eAcknowledgement\u003c/h2\u003e\u003cp\u003eThe authors are thankful to the Management and principal, P. V. P. College, Pravaranagar for providing laboratory facilities and constant encouragement during the work. The authors are also thankful to the SAIF, Panjab University, Chandigarh, for the spectral analysis.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\u003cli\u003e\u003cspan\u003eJ. Zho, P. Xiao, S. Han, M. Zulhumar, D. Wu, Preparation of magnetic copper ferrite nanoparticles as peroxymonosulfate activating catalyst for effective degradation of levofloxacin. Water Sci. Technol. \u003cb\u003e85\u003c/b\u003e(2), 645\u0026ndash;663 (2022)\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eV. Pushpalatha, Y.B. 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Sulfur Chem. \u003cb\u003e45\u003c/b\u003e(4), 459\u0026ndash;476 (2024)\u003c/span\u003e\u003c/li\u003e\u003c/ol\u003e"},{"header":"Tables","content":"\u003cp\u003eTable 3 is available in the Supplementary Files section.\u003c/p\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":true,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true},"keywords":"Copper ferrite nanoparticles, pyrano[2,3-c] pyrazoles, multi-component reaction, water, ethanol","lastPublishedDoi":"10.21203/rs.3.rs-5877830/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-5877830/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eAn efficient CuFe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e nonocatalyzed was synthesized by using triton X-100 as a surfactant in water. The synthesized catalyst was characterized by using FTIR, XRD, EDX, SEM and TEM techniques. The nanocatalyst successfully synthesized pyrano[2,3-c] pyrazoles derivatives through one-pot four-component condensation of aromatic aldehydes, malononitrile, ethyl acetoacetate and hydrazine hydrate in the presence of a catalytic amount of CuFe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e as an efficient and inexpensive nanocatalyst. The yield of pyrano[2,3-c] pyrazoles was studied using various reaction parameters such as the amount of catalyst, type of solvent, reaction condition and time. This multicomponent reaction is simple, reduces toxicity, has a short reaction time and has a high product yield. All the synthesized pyrano[2,3-c] pyrazoles derivatives were characterized by IR, \u003csup\u003e1\u003c/sup\u003eH NMR, and\u003csup\u003e 13\u003c/sup\u003eC NMR analysis. Additionally, the catalyst was reusable for up to four reaction runs.\u003c/p\u003e","manuscriptTitle":"Copper ferrite nanoparticles: an efficient catalyst for the one-pot four-component synthesis of pyrano[2,3-c] pyrazole derivatives","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-01-24 13:15:56","doi":"10.21203/rs.3.rs-5877830/v1","editorialEvents":[{"type":"communityComments","content":0}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"df01c969-b41d-44e7-9a51-f9079302649a","owner":[],"postedDate":"January 24th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"posted","subjectAreas":[],"tags":[],"updatedAt":"2025-01-28T12:39:02+00:00","versionOfRecord":[],"versionCreatedAt":"2025-01-24 13:15:56","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-5877830","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-5877830","identity":"rs-5877830","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}