A new effective method for the construction of 1,4,2-benzodithiazine and 1,2,3-benzoxathiazine scaffolds, based on the use of easily accessible N-chlorosulfonyltrichloroacetimidoyl chloride, has been developed. Reactions of thiophenols involved an initial nucleophilic substitution at the imine carbon atom with a thiol sulfur atom, followed by intramolecular sulfonylation of the benzene ring. Phenols exhibit opposite regioselectivity and react by electrophilic imidoylation of the ortho-carbon atom of the benzene ring (C-C bond formation) and sulfonation of the phenol oxygen atom. Synthesized 1,4,2-benzodithiazine-1,1-dioxides exhibit growth-stimulating activity on monocotyledonous winter wheat "Bezosta" and dicotyledonous plants Barbarea arcuate.

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A new effective method for the construction of nitrogen heterocycles incorporating endocyclic pharmacophore sulfonamide fragment, based on the use of easy accessible N-(chlorosulfonyl)imidoyl chloride, CCl3C(Cl)=NSO2Cl (1), has been developed. Thus, a reaction of 1 as bielectrophilic 1,3-C–N–S reagent with benzylamines that act as 1,4-N–C–C-C binucleophiles, affords respective 1,2,4-benzothiadiazepine-1,1-dioxides. On the other hand, 1 reacts with alkenyl amines with the formation of respective N-alkenyl amidines undergoing Lewis acids initiated intramolecular cyclization to afford derivatives of 1,2,4-thiadiazines and 1,2,4-thiadiazocines bearing a halomethyl group able for further functionalization. The first examples of electrophilic heterocyclization of the chlorosulfonyl group onto an alkenyl or alkynyl group have been revealed.