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Selective Access to 3-Cyano-1H-indoles, 9H-Pyrimido[4,5-b]indoles, or 9H-Pyrido[2,3-b]indoles through Copper-Catalyzed One-Pot Multicomponent Cascade Reactions

Bin Li, Shenghai Guo, Ju Zhang, Xinying Zhang* and Xuesen Fan*

*School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. China, Email: xuesen.fanhtu.cn, xinyingzhanghtu.cn

B. Li, S. Guo, J. Zhang, X. Zhang, X. Fan, J. Org. Chem., 2015, 80, 5444-5456.

DOI: 10.1021/acs.joc.5b00239 (free Supporting Information)


 

Abstract

A copper-catalyzed one-pot multicomponent cascade reaction of 1-bromo-2-(2,2-dibromovinyl)benzenes with aldehydes and aqueous ammonia enables a selective synthetis of various indole derivatives. 3-Cyano-1H-indoles, 9H-pyrimido[4,5-b]indoles, or 9H-pyrido[2,3-b]indoles depending on the concentration of ammonia, the molar ratio of reagents, and the structural features of the aldehyde.

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Key Words

indoles, multicomponent reactions, oxygen


ID: J42-Y2015