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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 (free Supporting Information)


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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



Key Words

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


ID: J54-Y2020