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A series of novel, one-pot, four components synthetic procedure has been developed for the synthesis of thioalkylated benzimidazole-linked 4-substituted mercaptoimidazole molecular hybrids and their benzyl derivatives ( 4a–j ) and ( 5a–f ) were synthesized by the reaction of 5-amino-2-mercaptobenzimidazole, with different substituted phenacyl bromides/aryl alkyl halides in the presence of glacial acetic acid and fused sodium acetate under reflux condition to give corresponding intermediates. These compounds on further reaction with ammonium thiocyanate  via  multi-component reaction to give the title compounds ( 4a–j ) and ( 5a–f).  All the newly synthesized compounds were well characterized by their spectral and analytical studies. This procedure includes several advantages such as transition metal-free, catalyst-free, mild reaction temperature, shorter reaction time, and gives good to excellent yields without any column purification techniques. Further, mechanistic insight into the formation of the final products has also been provided based on their density functional theory (DFT) studies.

synthetic communications

Synthesis, characterization and Density Functional Theory of novel one-pot thioalkylated benzimidazole-linked 4-substituted mercaptoimidazole molecular hybrids  via  multi-component approach