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Rearrangement of 2-amino-4-(trifluoromethyl)oxazoles to hydantoins

✍ Scribed by Jon P. Lawson; Karey A. VanSant

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
216 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Reaction of 2‐amino‐4‐trifluoromethyloxazoles with excess bromine in acetic acid/sodium acetate gives 5‐acetoxyhydantoins. The 5‐bromooxazoles are intermediates in the reaction.

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Rearrangement of 2-Amino-4-(trifluoromethyl)oxazoles to Hydantoins. -5-Halogenation of the oxazoles (I) with one equivalent of bromine initially furnishes 5-bromooxazoles (II) which are further transformed into the 5-acetoxyhydantoins (IV) and (V), respectively. This rearrangement takes place as a

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