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 language | English |
---|---|
Pages (from-to) | 2361-2364 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 37 |
Issue number | 14 |
DOIs | |
State | Published - Apr 1 1996 |