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Issue 3, 2017
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Rapid access to N-(indol-2-yl)amides and N-(indol-3-yl)amides as unexplored pharmacophores

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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.

Graphical abstract: Rapid access to N-(indol-2-yl)amides and N-(indol-3-yl)amides as unexplored pharmacophores

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Supplementary files

Article information


Submitted
01 Dec 2016
Accepted
14 Dec 2016
First published
14 Dec 2016

This article is Open Access

Org. Biomol. Chem., 2017,15, 576-580
Article type
Communication

Rapid access to N-(indol-2-yl)amides and N-(indol-3-yl)amides as unexplored pharmacophores

T. A. Reekie, S. M. Wilkinson, V. Law, D. E. Hibbs, J. A. Ong and M. Kassiou, Org. Biomol. Chem., 2017, 15, 576
DOI: 10.1039/C6OB02622B

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