Redox Cyclization of Amides and Sulfonamides with Nitrous Oxide for Direct Synthesis of Heterocycles

Zhencheng Lai, Chaorong Wang, Jiaming Li and Sunliang Cui*

*Institute of Drug Discovery and Design, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China, Email: slcuizju.edu.cn

Z. Lai, C. Wang, J. Li, S. Cui, Org. Lett., 2020, 22, 2017-2021.

DOI: 10.1021/acs.orglett.0c00397

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Abstract

A redox cyclization of amides and sulfonamides with nitrous oxide enables a direct and simple synthesis of heterocycles. Various amides and sulfonamides could undergo directed ortho metalation (DoM) by treatment with BuLi, and the lithium intermediate can be trapped by N₂O gas to achieve redox cyclization.

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proposed mechanism

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Key Words

directed ortho metalation, 1,2,3-benzotriazine-4(3H)-ones, nitrous oxide

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ID: J54-Y2020