Polyfunctional imidazoles: XIV. 4-sulfonyl-5-formyl-1H-imidazoles

Oxidative chlorination of 1-aryl-4-benzylsulfanyl-1 H -imidazole-5-carbaldehydes gave 1-aryl-5-formyl-1 H -imidazole-4-sulfonyl chlorides which reacted with secondary amines and phenols to produce the corresponding N , N -disubstituted 5-formylimidazole-4-sulfonamides and aryl sulfonates. The reaction of 1-aryl-5-formyl-1 H -imidazole-4-sulfonyl chlorides with sodium azide, followed by reduction of the resulting sulfonyl azides, led to the formation of N -unsubstituted 5-formylimidazole-4-sulfonamides, and the reaction with alcohols, to 5-formylimidazole-4-sulfonic acids.