Search

A new one-pot palladium-catalyzed process between N-tosylhydrazones, N-(dihalophenyl)-imidates, and amines was designed. This reaction involves Barluenga cross-coupling and N-arylation followed by cyclization to produce functionalized benzimidazoles. During this transformation, one CC bond and two CN bonds were created by a single palladium-catalyzed reaction. Depending on the starting materials, a library of 5-(1-arylvinyl)-1H-benzimidazoles was synthesized. Among several arylvinylbenzimidazole derivatives evaluated, one compound exhibits excellent antiproliferative activity in the nanomolar concentration range against human colon carcinoma cell lines (HCT-116) and human lung adenocarcinoma epithelial cell lines (A549).