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

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 t...

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Veröffentlicht in:Journal of organic chemistry 2009-09, Vol.74 (18), p.7052-7058
Hauptverfasser: Ohta, Yusuke, Chiba, Hiroaki, Oishi, Shinya, Fujii, Nobutaka, Ohno, Hiroaki
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Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo901328q