Synthesis of 2-aryl-2H,4H-imidazo[4,5-d][1,2,3]triazoles from triethyl N-(1-ethyl-2-methyl-4-nitro-1H-imidazol-5-yl)phosphorimidate by reaction with aryl isocyanates

Abstract

The synthesis of a series of 2-aryl-2H,4H-imidazo[4,5-d][1,2,3]triazoles is reported. These compounds are obtained in moderate to good yields by reaction of triethyl N-(1-ethyl-2-methyl-4-nitro-1H-imidazol-5-yl)phosphorimidate with aryl isocyanates. The X-ray crystal structures of triethyl (N-1-methyl-4-nitro-1H-imidazol-5-yl)phosphorimidate and a 2-(4-trifluoromethylphenyl) substituted 2H,4H-imidazo[4,5-d][1,2,3]triazole are reported. Spectroscopic evidence is provided for a carbodiimide intermediate proposed in the reaction mechanism.