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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 16
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Original Articles

Synthesis of Benz[d]oxazolones Involving Concomitant Acetyl Migration from Oxygen to Nitrogen

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Pages 2377-2388 | Received 26 May 2009, Published online: 26 Jul 2010
 

Abstract

Heating of o-acetoxybenzoyl azides 6–10 in toluene leads to the Curtius reaction, which, when followed by closure of oxazolone ring with concomitant migration of acetyl group from oxygen to nitrogen, produces 3-acetoxybenz[d]oxazol-2(3H)-ones 11–15, which undergo hydrolysis with hot dilute hydrochloric acid to furnish benz[d]oxazol-2(3H)-ones 17–21. Thermal reaction of 2-hydroxy-5-nitrobenzoyl azide (22) in toluene finally yields a mixture of 5-nitrobenz[d]oxazol-2(3H)-one (20) and 5-nitrobenz[d]isoxazol-3(2H)-one (23).

ACKNOWLEDGMENTS

We thank A. Acharya and P. Ghosh for 1H NMR and 13C NMR spectral measurements. One of the authors (S. G.) is thankful to the University Grants Commission, New Delhi, and the Council for Scientific and Industrial Research, New Delhi, for a research fellowship.

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