In-Water Synthesis of 5-Thiolated 1,2,3-Triazoles from β-Thioenaminones by Diazo Transfer Reaction.

The synthesis of 1,2,3-triazoles with a sulfur-based side chain has been accessed with the metal-free annulation reactions of readily available β-thiolated enaminones and tosyl hydrazine. By these reactions with water as the only medium, a broad array of 5-thiolated 1,2,3-triazoles have been synthesized with generally good to excellent yields. Except using TMEDA (N,N,N',N'-tetramethylethylenediamine) as the only base promoter, not any other catalyst or additive is required, thus providing an efficient and environmentally benign method for useful 1,2,3-triazole synthesis.