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Construction of Nitrogen Heterocycles Bearing an Aminomethyl Group by Copper-Catalyzed Domino Three-Component Coupling-Cyclization

Yusuke Ohta, Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii* and Hiroaki Ohno*

*Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan, Email: hohnopharm.kyoto-u.ac.jp, nfujiipharm.kyoto-u.ac.jp

Y. Ohta, H. Chiba, S. Oishi, N. Fujii, H. Ohno, J. Org. Chem., 2009, 74, 7052-7058.

DOI: 10.1021/jo901328q (free Supporting Information)



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Abstract

2-Ethynylanilines were converted to various substituted 2-(aminomethyl)indoles in good to excellent yields in the presence of a secondary amine and an aldehyde by a copper-catalyzed domino three-component coupling-cyclization. Utilizing this domino reaction and C-H functionalization at the indole C-3 position, polycyclic indoles were readily synthesized.

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Key Words

Indoles, Multicomponent Reactions


ID: J42-Y2009-2730