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An efficient and rapid microwave-assisted synthesis of 1-acetyl-1H-indol-3-YL acetates

Parshotam, J. P., Brazier, J. A., Bovill, R. and Osborn, H. M. I. (2016) An efficient and rapid microwave-assisted synthesis of 1-acetyl-1H-indol-3-YL acetates. Current Microwave Chemistry, 3 (3). pp. 247-257. ISSN 2213-3364

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To link to this item DOI: 10.2174/2213335603666160108001556

Abstract/Summary

An efficient and rapid synthesis of 1-acetyl-1H-indol-3-yl acetate 1 and its derivatives 7 via the microwave-assisted cyclisation and decarboxylation of 2-[(carboxymethyl)amino]benzoic acids 5 is described. The latter were left to react with acetic anhydride using triethylamine as the base and were subjected to microwave irradiation for 1 minute, at 80 °C with initial power of 300 W. The target 1-acetyl-1H-indol-3-yl acetate 1 and derivatives 7 were isolated in 34-71% yield. In particular, synthesis of 1-acetyl-6-(trifluoromethyl)-1H-indol-3-yl acetate 7f and 1-acetyl-3-methyl-1H-indol-3-yl acetate 7h is reported for the first time.

Item Type:Article
Refereed:Yes
Divisions:Interdisciplinary centres and themes > Chemical Analysis Facility (CAF)
Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Medicinal Chemistry Research Group
ID Code:51462
Uncontrolled Keywords:microwave; synthesis; cyclisation; indoxyls; indoles
Publisher:Bentham

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