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

Arthur G. Romero, William H. Darlington, E. Jon Jacobsen, John W. Mickelson

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

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-2-benzimidazolinone. Hydrogenation over Pd/C cleaves the methoxy group to afford the N-substituted 2-benzimidazolinone.

Original languageEnglish
Pages (from-to)2361-2364
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number14
DOIs
StatePublished - Apr 1 1996

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