Carbon Disulfide Promoted Reactions of 2-Chloro-4, 5-dihydro-imidazole with Some N-Nucleophiles

Abstract

The reactions of 2-chloro-4, 5-dihydroimidazole 1 with o-substituted anilines and azoles promoted by carbon disulfide have been carried out. Ab initio MO calculations were used to elucidate the mechanism of the reaction of 1 with N-nucleophilic reagents. A facile synthesis of 2-(4, 5-dihydroimidazol-2-yl)-1H-indazole 3e bearing structural resemblances to 2-BFI, a potent and selective agonist of imidazoline I₂ receptors, is also described. Structure of 3e was confirmed by NMR spectroscopy and X-ray analysis.