95384-59-1Relevant articles and documents
Copper-catalyzed regioselective 2-amination of o-haloanilides with aqueous ammonia
Tang, Yan-Ling,Li, Mei-Ling,Gao, Jin-Chun,Sun, Yun,Qu, Lu,Huang, Feng,Mao, Ze-Wei
supporting information, (2021/04/02)
An efficient Cu(II)-vasicine catalytic system has been developed for intramolecular C[sbnd]N bond formation. In this way, regioselective 2-amination of o-haloanilides with aqueous ammonia in EtOH has been achieved. This strategy provides several advantages, such as good regioselectivity, high yields and functional group tolerance.
Conversion of sterically hindered diacylated 1,2-phenylenediamines into 2-substituted benzimidazoles
Charton, Julie,Girault-Mizzi, Sophie,Sergheraert, Christian
, p. 492 - 497 (2007/10/03)
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, cycllzation 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.
SOLID-PHASE REACTIONS OF AROMATIC AMINES WITH CARBOXYLIC ACIDS UNDER CONDITIONS OF SHEAR DEFORMATION AND HIGH PRESSURE
Leont'ev, A. I.,Zharov, A. A.,Chistotina, N. P.
, p. 1680 - 1684 (2007/10/02)
Solid mixtures of carboxylic acids and aromatic amines react under shear deformation at high pressure (to 8 GPa) for form amides, in the case of ortho-phenylenediamine-substituted benzimidazoles are formed.Under these conditions the conversion rates are hundreds of thousands of times higher than when the same processes are carried out in liquid phase.The cyclization reaction is accelerated to a lesser degree than the reaction of formation of the corresponding amide.The increase of the length of the carboxylic acid radical prevents the cyclization reaction. Keywords: shear deformation, high pressure, aromatic amines, carboxylic acids, amide, benzimidazole, amidization, cyclization.