Copper-Catalyzed Aerobic Oxidative Cyclization of 2-Alkynylanilines with Nitrosoarenes: Synthesis of Organic Solid Mechanoluminescence Compounds of 4-Oxo-4H-cinnolin-2-ium-1-ide

Xiaolan Fang, Ji Cao, Weijie Ding, Huile Jin, Xiaochun Yu* and Shun Wang*

*College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou, 325035, P. R. China, Email: xiaochunyuwzu.edu.cn, shunwangwzu.edu.cn

X. Fang, J. Cao, W. Ding, H. Jin, X. Yu, S. Wang, Org. Lett., 2021, 23, 1228-1233.

DOI: 10.1021/acs.orglett.0c04186

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Abstract

An efficient Cu(I)/DMAP/air system enables a one-pot synthesis of 4-oxo-4H-cinnolin-2-ium-1-ides from substituted 2-alkynylanilines and nitrosoarenes. The use of an inexpensive copper catalyst and molecular oxygen as the oxygen source and the oxidant make this an attractive green protocol.

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proposed mechanism

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Key Words

benzo-fused N-heterocycles, oxygen

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ID: J54-Y2021