Conversion of sterically hindered diacylated 1,2-phenylenediamines into 2-substituted benzimidazoles.
A series of bulky 2-substituted benzimidazoles was designed in order to find new leads for several biological targets. Formation by cyclodehydration from their monoacylated counterparts was shown to be strongly dependent upon the nature of the acyl group. In the case of a dicyclohexylmethyl group, cyclization was only observed in a p-toluenesulfonic acid/toluene mixture from the symmetrical diacylated precursor. Analysis of the mechanism was begun starting from mixed diacylated derivatives.
Charton
Julie
J
UMR CNRS 8525, Universite de Lille II, Institut de Biologie et Institut Pasteur de Lille, 1 rue du Professeur Calmette, B.P. 447, 59021 Lille cedex, France. jcharton@pharma.univ-lille2.fr
Girault-Mizzi
Sophie
S
Sergheraert
Christian
C
D000107:Acetylation; D001562:Benzimidazoles / Q000032:analysis* / Q000737:chemistry*; D010655:Phenylenediamines / Q000032:analysis* / Q000737:chemistry*; D013237:Stereoisomerism
D001562:Benzimidazoles; D010655:Phenylenediamines