An efficient protocol for the formation of aminothiatriazoles from thiocarbamoylimidazolium salts

A new protocol for the formation of substituted aminothiatriazoles from thiocarbamoylimidazolium salts is outlined. Thiocarbamoylimidazolium salts are synthesized from the corresponding amines by treatment with thiocarbonyldiimidazole (TCDI) followed by methylation with iodomethane. Thiocarbamoylimidazolium salts are shown to act as thiocarbamoyl cation equivalents. Substitution of the salts by azide anion followed by electrocyclization affords substituted aminothiatriazoles in good to excellent yields.