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Synthesis 2004(16): 2653-2658  
DOI: 10.1055/s-2004-831228
PAPER
© Georg Thieme Verlag Stuttgart · New York

N-Acylation of 5-Substituted Indoles with Carboxylic Acids via DCC Coupling

John B. Bremner*, Siritron Samosorn, Joseph I. Ambrus
Institute for Biomolecular Science and Department of Chemistry, University of Wollongong, N.S.W. 2522, Australia
Fax: +61(2)42214287; e-Mail: john_bremner@uow.edu.au;
Further Information

Publication History

Received 28 June 2004
Publication Date:
22 September 2004 (online)

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Abstract

A method for the N-acylation of 5-substituted indoles with carboxylic acids using DCC and DMAP is presented. High yields were obtained when an electron-withdrawing group was present at C-5, however the method was less effective with a C-5 electron-donating group.

Key words

N-acylation - indoles - carboxylic acids - DCC coupling - DMAP

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