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Type: Journal article
Title: Rapid access to N-(indol-2-yl)amides and N-(indol-3-yl)amides as unexplored pharmacophores
Author: Reekie, T.A.
Wilkinson, S.M.
Law, V.
Hibbs, D.E.
Ong, J.A.
Kassiou, M.
Citation: Organic and Biomolecular Chemistry, 2017; 15(3):576-580
Publisher: Royal Society of Chemistry
Issue Date: 2017
ISSN: 1477-0520
Statement of
Tristan A. Reekie, Shane M. Wilkinson, Vivian Law, David E. Hibbs, Jennifer A. Ong and Michael Kassiou
Abstract: Preparation of N-(indol-2-yl)amides and N-(indol-3-yl)amides are scarce in the scientific literature due to unstable intermediates impeding current reported syntheses. We have employed cheap and readily available substrates in the Curtius rearrangement of indole-3-carboxazide to afford N-(indol-3-yl)amides. The reaction is observed for alkyl and aryl carboxylic acids and both N-substituted or 1H-indole derivatives are tolerated. This approach was extended to the preparation of N-(indol-2-yl)amides from the corresponding indole-2-carboxazides.
Description: Published on 14 December 2016.
Rights: This journal is © The Royal Society of Chemistry 2017. Open Access Article. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
DOI: 10.1039/c6ob02622b
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