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The reaction of N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides with 2-mercaptoimidazoles affords N(2-phenylimidazo[2,1-b][1,3]thiazol-3-yl)arenesulfonamides or N-(2-phenyl[1,3]thiazolo[3,2-a]benzimidazol-3yl)arenesulfonamides. Formation of the annulated heterocyclic derivatives is tentatively triggered by a nucleophilic addition of mercaptoimidazole to the activated azomethine group of halogen-containing imines followed by intramolecular heterocyclization and aromatization.

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Regioselective reaction of imidazole-2-thiols with N-sulfonylphenyldichloroacetaldimines: en route to novel sulfonylamino-substituted imidazo[2,1-b]thiazoles and thiazolo[3,2-a]benzimidazoles