Synthesis, spectral characteristics and supramolecular organization of new non-symmetrically 1,6- and 1,4-dialkyl- 3а,6а-diphenylglycolurils

Synthesis, spectral characteristics and supramolecular organization of new non-symmetrically 1,6- and 1,4-dialkyl- 3а,6а-diphenylglycolurils | 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 Synthesis, spectral characteristics and supramolecular organization of new non-symmetrically 1,6- and 1,4-dialkyl- 3а,6а-diphenylglycolurils Vladimir V. Baranov, Maria M. Antonova, Svetlana A. Soloveva, and 2 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-7809756/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 The two approaches for the preparation of non-symmetrically 1,6- and 1,4-dialkyl-3a,6a-diphenylglycolurils were developed as a result of studying new regioselective reactions of 1-alkyl-5-hydroxy-4,5-diphenyl-1 H -imidazole-2(5 H )-ones with 1-alkylureas. A selectivity of the formation of 1,6-dialkyl isomers was detected. The 1,6- and 1,4-dialkyl-3а,6а-diphenylglycolurils were isolated in 55–77% and 11–29% yields respectively, and characterized by 1 H NMR and 13 C NMR spectroscopy. The mechanism for the formation of 1,6- and 1,4-isomers was proposed. Self-organization of 1-ethyl-6-methyl-3a,6a-diphenylglycoluril and its crystallosolvates with HCOOH, dioxane and a mixture of Py and H 2 O (in a 1:1 ratio), 1-butyl-3a,6a-dipheny-4-propylglycoluril, crystallosolvate of 1-ethyl-3a,6a-diphenyl-6-propylglycoluril with MeCN was studied by X-ray diffraction analysis. Based on the analysis of the crystal packing of structures, it was found that the self-organization of studied molecules in crystals of 1,4- and 1,6-disubstituted 3a,6a-diphenylglycolurils demonstrates new examples of supramolecular synthons with \(\:{R}_{2}^{2}\left(8\right)\) motif based on an N-H…O=С hydrogen bond. Glycolurils Supramolecular organization 1-Alkylureas Regioselective condensation X-Ray Full Text Additional Declarations No competing interests reported. Supplementary Files mmc.docx 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-7809756","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":534125113,"identity":"6011fe59-701c-4dfa-903a-a7708c5185f3","order_by":0,"name":"Vladimir V. 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3а,6а-diphenylglycolurils","fulltext":[],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":false,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":true,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":true,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":true,"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":"Glycolurils, Supramolecular organization, 1-Alkylureas, Regioselective condensation, X-Ray","lastPublishedDoi":"10.21203/rs.3.rs-7809756/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-7809756/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eThe two approaches for the preparation of non-symmetrically 1,6- and 1,4-dialkyl-3a,6a-diphenylglycolurils were developed as a result of studying new regioselective reactions of 1-alkyl-5-hydroxy-4,5-diphenyl-1\u003cem\u003eH\u003c/em\u003e-imidazole-2(5\u003cem\u003eH\u003c/em\u003e)-ones with 1-alkylureas. A selectivity of the formation of 1,6-dialkyl isomers was detected. The 1,6- and 1,4-dialkyl-3а,6а-diphenylglycolurils were isolated in 55\u0026ndash;77% and 11\u0026ndash;29% yields respectively, and characterized by \u003csup\u003e1\u003c/sup\u003eH NMR and \u003csup\u003e13\u003c/sup\u003eC NMR spectroscopy. The mechanism for the formation of 1,6- and 1,4-isomers was proposed. Self-organization of 1-ethyl-6-methyl-3a,6a-diphenylglycoluril and its crystallosolvates with HCOOH, dioxane and a mixture of Py and H\u003csub\u003e2\u003c/sub\u003eO (in a 1:1 ratio), 1-butyl-3a,6a-dipheny-4-propylglycoluril, crystallosolvate of 1-ethyl-3a,6a-diphenyl-6-propylglycoluril with MeCN was studied by X-ray diffraction analysis. Based on the analysis of the crystal packing of structures, it was found that the self-organization of studied molecules in crystals of 1,4- and 1,6-disubstituted 3a,6a-diphenylglycolurils demonstrates new examples of supramolecular synthons with \u003cspan class=\"InlineEquation\"\u003e\u003cspan class=\"mathinline\"\u003e\\(\\:{R}_{2}^{2}\\left(8\\right)\\)\u003c/span\u003e\u003c/span\u003e motif based on an N-H\u0026hellip;O=С hydrogen bond.\u003c/p\u003e","manuscriptTitle":"Synthesis, spectral characteristics and supramolecular organization of new non-symmetrically 1,6- and 1,4-dialkyl- 3а,6а-diphenylglycolurils","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-10-27 14:31:00","doi":"10.21203/rs.3.rs-7809756/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":"4872fcaa-5012-4ea4-9b75-3fdbe40f6f4b","owner":[],"postedDate":"October 27th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"posted","subjectAreas":[],"tags":[],"updatedAt":"2025-10-30T07:10:27+00:00","versionOfRecord":[],"versionCreatedAt":"2025-10-27 14:31:00","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-7809756","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-7809756","identity":"rs-7809756","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}