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Attempted synthesis of ethyl 3,4-dihydro-2H-1,4-benzoxazine-3-carboxylate and 3-acetate derivatives

✍ Scribed by Stanislas Mayer; Axelle Arrault; GÉRald Guillaumet; Jean-Yves Mérour

Publisher: Journal of Heterocyclic Chemistry
Year: 2001
Tongue: English
Weight: 65 KB
Volume: 38
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570380133

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✦ Synopsis

Abstract

Ethyl 3,4‐dihydro‐2__H__‐1,4‐benzoxazine‐3‐carboxylate derivatives 2 were obtained and isolated in low yields from the condensation of 2‐aminophenol and ethyl 2,3‐dibromopropanoate. They can be obtained by hydrogenation of ethyl 2__H__‐1,4‐benzoxazine‐3‐carboxylate in satisfactory yield. Using 2‐iminophenol did not direct the condensation with ethyl 2,3‐dibromopropanoate towards 2 but was fruitfull for the preparation of ethyl 2‐(4‐benzyl‐3,4‐dihydro‐2__H__‐1,4‐benzoxazin‐3‐yl)acetate from ethyl bromocrotonate.

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