Journal of Organic Chemistry 2009-09-18

Construction of nitrogen heterocycles bearing an aminomethyl group by copper-catalyzed domino three-component coupling-cyclization.

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

Index: J. Org. Chem. 74(18) , 7052-8, (2009)

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Abstract

A direct approach to 2-(aminomethyl)indoles by copper-catalyzed domino three-component coupling-cyclization of 2-ethynylanilines with a secondary amine and aldehyde has been developed. By use of a cyclic or acyclic secondary amine and aldehyde (paraformaldehyde, aliphatic or aromatic aldehydes) in the presence of 1 mol % of CuBr, 2-ethynylanilines were converted to a variety of substituted 2-(aminomethyl)indoles in good to excellent yields. Utilizing this domino reaction and C-H functionalization at the indole C-3 position, polycyclic indoles were readily synthesized. Construction of benzo[e][1,2]thiazine and indene motifs by the reaction of sulfonamide and malonate congeners is also presented.