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

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• 作者：Yusuke Ohta ; Hiroaki Chiba ; Shinya Oishi ; Nobutaka Fujii ; Hiroaki Ohno
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：September 18, 2009
• 年：2009
• 卷：74
• 期：18
• 页码：7052-7058
• 全文大小：878K
• 年卷期：v.74,no.18(September 18, 2009)
• ISSN：1520-6904

文摘

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.