Synthesis of dimethyl substituted benzimidazoles containing cyclopropane fused onto five to eight membered [1,2- a]alicyclic rings and influence of methyl group substituents on cytotoxicity of benzimidazolequinones

Abstract

Upon thermolysis 5,6-dimethyl- N-[(allyl, but-3-enyl, pent-4-enyl and hex-5-enyl-benzimidazol-2-yl)methylene]-( trans)-2,3-diphenylaziridin-1-amines (Eschenmoser hydrazones) form cyclopropane fused onto pyrrolo-, pyrido-, azepino- and azocino[1,2- a]benzimidazoles in 70, 50, 77 and 11% yield, respectively. The latter reaction also gave carbene insertion products. Dimethyl group substituents were found to significantly reduce the cytotoxicity of benzimidazolequinone towards human skin fibroblast cells.