Synthesis of 2-imino-1,3-dithiolanes containing trimethylsilylethynylthiolato groups

An efficient, eco-friendly, and simple one-pot approach for the synthesis of 2-imino-1,3-dithiolanes via reaction of allyl chloride, primary amines, carbon disulfide, and I₂ under solvent-free conditions is presented. The obtained 5-iodomethyl-2-imino-1,3-dithiolanes were converted into silyl-protected terminal alkynyl sulfides substituted 2-imino-1,3-dithiolanes by treatment with lithium 2,2,2-tris(trimethylsilyl)ethanedithioate, produced by the reaction of tris(trimethylsilyl)methyllithium (TsiLi) with CS₂.