Transition-Metal-Free Base-Promoted Divergent Synthesis of 5-Amide-1,2,3-triazole and 5-Imide-1,2,3-triazole Derivatives

A transition-metal-free, base-promoted, three-component reaction involving various nitriles, azides, and isothiocyanates has been developed for the divergent synthesis of fully substituted 5-amide-1,2,3-triazole and 5-imide-1,2,3-triazole derivatives. The reaction proceeded via the cycloaddition of nitriles and azides in the presence of a base followed by the capture of the triazolamine and triazole nitrogen anion intermediate with isothiocyanates. This method is featured by being transition metal free and having broad substrate scope, complete regioselectivity, and late-stage functionalization.