Abstract: A novel and selective one-pot synthetic method of imidazole and benzimidazole derivatives has been developed. Three series of target compounds, 1-(ω-haloalkyl) imidazoles 3a-3e, bis-imidazoles 5a-5b and tri-imidazoles 6a-6b have been synthesized by the selective quaterisation of 1H-imidazole-1-propanenitrile (1) with α, ω-dihalide, bis(bromomethyl) benzene or tri(bromomethyl) benzene to obtain imidazolium salts, following by Hoffmann-type elimination. Similarly, benzimidazole analogues 7 and 8 were also prepared. It is found that important factors affecting this selective quaterisation are the solvent, temperature, structure and amount of halides.

Key words: Imidazole derivative, Quaterisation, Hoffmann-type elimination