Synthesis of Polyiodides of N- and S-S-Acetonyl Derivatives of 2,2′-(Disulfanediyl)- and 2,2′-[Alkanediylbis(sulfanyl)]-bisbenzimidazolium

Abstract

2,2′-(Disulfanediyl)- and 2,2′-[alkanediylbis(sulfanyl)]-bisbenzimidazoles react with aliphatic, aromatic, and heterocyclic α-iodoketones in the presence of elemental iodine without solvents, basic media, and catalysts to afford polyiodides of the N- and S-S-acetonyl derivatives. The selectivity of the alkylation reaction depends on the structure of the starting substrates. In the case of the disulfide, the reaction involves the sulfur atoms to give hitherto unknown disulfanium derivatives. The introduction of an organic bridge between the sulfur atoms leads to the formation of polyiodides of 2,2′-[alkanediylbis(sulfanyl)]bisbenzimidazole N-acetonyl derivatives.