Synthesis of Benzotriazepin-1-ones via Decarboxylative [4 + 3]-Annulation of Isatoic Anhydrides with Nitrile Imines.

J Org Chem

Department of Chemistry, College of Natural Science, Kyonggi University, 154-42 Gwanggyosan-ro, Yeongtong-gu, Suwon 16227, Republic of Korea.

Published: June 2023

A novel and streamlined approach to synthesizing benzotriazepin-1-ones has been developed through a hexafluoroisopropanol-promoted decarboxylative cascade reaction between isatoic anhydrides and hydrazonoyl chloride. The [4 + 3] annulation of hexafluoroisopropyl 2-aminobenzoates with nitrile imines, generated in situ, is a key feature of this innovative reaction. This approach has offered a simple and efficient method for synthesizing a broad range of structurally intricate and highly functional benzotriazepinones.

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http://dx.doi.org/10.1021/acs.joc.3c00524DOI Listing

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