Tetrahedron letters

Oxidative cyclization of acyclic ureas with bis (trifluoroacetoxy) iodobenzene to generate N-substituted 2-benzimidazolinones

…, WH Darlington, EJ Jacobsen, JW Mickelson

Index: Romero, Arthur G.; Darlington, William H.; Jacobsen, E. Jon; Mickelson, John W. Tetrahedron Letters, 1996 , vol. 37, # 14 p. 2361 - 2364

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Citation Number: 31

Abstract

A facile method to synthesize N-substituted 2-benzimidazolinones from secondary aromatic amines is presented. Sequential treatment of a secondary aromatic amine with phosgene and methoxylamine afforded an acyclic 3-substituted 3-aryl-1-methoxy urea. Brief exposure of this urea to bis (trifluoroacetoxy) iodobenzene induced an oxidative cyclization to the ortho-position of the benzene ring, resulting in the formation of a 3-substituted 1-methoxy- ...

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