Carboxylic acid catalyzed three-component aza-Friedel-Crafts reactions in water for the synthesis of 3-substituted indoles

Seiji Shirakawa; Shu Kobayashi

doi:10.1021/ol062031q

Carboxylic acid catalyzed three-component aza-Friedel-Crafts reactions in water for the synthesis of 3-substituted indoles

Org Lett. 2006 Oct 12;8(21):4939-42. doi: 10.1021/ol062031q.

Authors

Seiji Shirakawa¹, Shu Kobayashi

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 17020341
DOI: 10.1021/ol062031q

Abstract

[reaction: see text] The carboxylic acid catalyzed three-component aza-Friedel-Crafts reactions of aldehydes, primary amines, and indoles in water have been developed. The aza-Friedel-Crafts products could be easily transformed to various 3-substituted indoles including biologically active compounds. This system offers a novel efficient method for the synthesis of 3-substituted indoles.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carboxylic Acids / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Water

Substances

Carboxylic Acids
Indoles
Water