Access to 2-Oxoazetidine-3-carboxylic Acids Derivatives via Thermal Microwave-Assisted Wolff Rearrangement of 3-Diazotetramic Acids in the Presence of Nucleophiles

chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry In this work, we report an efficient approach to 2-oxoazetidine-3-carboxylic acid derivatives based on thermally promoted Wolff rearrangement of diazo tetramic acids in the presence of nucleophiles. The method allows easy variation of the substituent in the exocyclic acyl group by introducing different N-, O- and S-nucleophilic reagents into the reaction. The reaction of chiral diazo tetramic acids leads exclusively to trans-diastereomeric β-lactams. The use of variously substituted diazo tetramic acids, including spirocyclic derivatives, as well as a wide range of nucleophiles provides access to a structural diversity of medically relevant 2-oxoazetidine-3-carboxylic acids amides and esters.

β-lactams; Wolff rearrangement; diazo tetramic acids; nucleophiles; thermolysis; spirocycles | Format: DOCX | Size: 5.3 MB | Download | When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information: Lyutin, I.; Krivovicheva, V.; Kantin, G.; Dar'in, D. Beilstein Arch. 2024, 202435. doi:10.3762/bxiv.2024.35.v1 Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below. Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero. © 2024 Lyutin et al.; licensee Beilstein-Institut. This is an open access work licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-archives.org/xiv/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this work could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.