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Ring Opening of 2-(Benzylamino)-2H-1,4-benzoxazin-3(4H)-ones and 2-Bromo-2H-1,4-benzoxazin-3(4H)-ones

✍ Scribed by Janez Ilaš; Danijel Kikelj

Publisher: John Wiley and Sons
Year: 2008
Tongue: German
Weight: 223 KB
Volume: 91
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200890069

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✦ Synopsis

Abstract

Substituted 2‐(benzylamino)‐2__H__‐1,4‐benzoxazin‐3(4__H__)‐ones are unstable under alkaline and acidic conditions, undergoing opening of the benzoxazinone ring. 2‐Bromo‐2__H__‐1,4‐benzoxazin‐3(4__H__)‐ones show similar degradation under alkaline conditions, while replacement of Br at C(2) to give 2‐hydroxy‐2__H__‐1,4‐benzoxazin‐3(4__H__)‐ones was observed only under mild alkaline conditions. Mechanisms of ring opening and degradation to 2‐aminophenol derivatives are proposed.

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