The aminobarbituric acid-hydantoin rearrangement

M Meusel, A Ambrozak, TK Hecker…

Index: Meusel, Manuela; Ambrozak, Agnieszka; Hecker, Thomas K.; Guetschow, Michael Journal of Organic Chemistry, 2003 , vol. 68, # 12 p. 4684 - 4692

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Citation Number: 47

Abstract

A general synthesis protocol for the generation of tri-and tetrasubstituted 5- carbamoylhydantoins is described. Starting from barbituric acids and following bromination and reaction with primary amines, 5-aminobarbituric acids 3a-s and 8 were prepared. Compounds 3 and 8 were subjected to different conditions of a base-catalyzed rearrangement reaction to yield the 1, 5, 5-trisubstituted hydantoins 4a-s and the 1, 3, 5, 5- ...