Tetrahedron letters

Syntheses, addition–eliminations, and addition–displacements of 5-(bromomethylene) hydantoins

NC Mathur, SK Wong, H Shechter

Index: Mathur, Naresh C.; Wong, Sau K.; Shechter, Harold Tetrahedron Letters, 2003 , vol. 44, # 27 p. 5141 - 5144

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Citation Number: 5

Abstract

5-(Bromomethylene) hydantoins, prepared from bromopyruvic acid and ureas in the presence of BF3, react with various nitrogen, phosphorus, sulfur, and carbon nucleophiles by addition–elimination to give the corresponding 5-(substituted-methylene) hydantoins. The 5-(bromomethylene) hydantoins also undergo acid-catalyzed reactions with nucleophiles by addition–displacement and addition–elimination processes.