Polyfunctional imidazoles: XIII.1 Addition and cyclization reactions of 1-aryl-4-chloro-5-(2-nitroethenyl)-1H-imidazoles with sulfur and nitrogen nucleophiles

Abstract

1-Aryl-4-chloro-5-(2-nitroethenyl)-1H-imidazoles reacted with thiols and aromatic amines via Michael addition to give 5-[(1-arylsulfanyl)-2-nitroethyl)]-4-chloro-1H-imidazoles and N-[1-(1-aryl-4-chloro-1H-imidazol-5-yl)-2-nitroethyl]anilines, respectively. [2 + 3]-Cycloaddition of the title compounds to sodium azide afforded 4-(4-chloro-1H-imidazol-5-yl)-1H-1,2,3-triazoles.