Synthesis of Benz[d]oxazolones Involving Concomitant Acetyl Migration from Oxygen to Nitrogen |
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Authors: | Sibdas Ray Sukla Ghosh |
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Affiliation: | 1. Department of Chemistry , University College of Science, University of Calcutta , Kolkata, India sibdas2002@yahoo.co.in;3. Department of Chemistry , Gobardanga Hindu College , Khantura, India |
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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). |
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Keywords: | Benz[d]oxazolone concomitant migration 5-nitrobenz[d]isoxazolone o-acetoxybenzoyl azides O to N acetyl migration |
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