PTSA-catalyzed selective synthesis and antibacterial evaluation of 1,2-disubstituted benzimidazoles.

Abstract

Herein, we developed a convenient and efficient method via protonation of p-toluenesulfonic acid promoted cyclocondensation of o-phenylenediamine and aldehydes for selectively synthesizing 1,2-disubstituted benzimidazoles. This method displayed broad substrate adaptability and afforded the desired products in moderate to excellent yield in short reaction time. The effect of different substituents on the yield was investigated by extending optimum reaction conditions, which was further confirmed by theoretical calculations. It suggested that the surface electrostatic potential of oxygen atom and nitrogen atom on the substrates played important role in the synthesis of 1,2-disubstituted benzimidazoles. Besides, the crystal structure of compound 2t in the orthorhombic space group P2(1)/c was presented. Also, the anti-mycolicibacterium smegmatis (MC2155) activity was evaluated using rifampicin as a positive control. The products (2a, 2b, 2c, 2i, 2j, 2k, 2m) showed good antibacterial activities which were comparable to rifampicin.