S- and N-alkylation of 2,2′-(alkane-α,ω-diyldisulfanediyl)-bis(1,3-benzothiazoles) with 1-iodopropan-2-one in the presence of iodine

Abstract

The alkylation of 2,2′-(methylenedisulfanediyl)- and 2,2′-(ethane-1,2-diyldisulfanediyl)bis-(1,3-benzothiazoles) with 1-iodopropan-2-one involves exclusively the exocyclic sulfur atoms. The presence of an electron-withdrawing carbonyl group between the bridging methylene units in 1,3-bis(1,3-benzothiazol-2-ylsulfanyl)propane-2-one forces the alkylation to occur at the endocyclic nitrogen atoms.