Electrochemical selective divergent C–H chalcogenocyanation of N-heterocyclic scaffolds

Abstract

An electrochemical direct selective C–H chalcogenocyanation approach for indolizine derivatives under mild conditions has been described. Cyclic enone-fused, chromone-fused and 2-substituted indolizines possessing EDGs (electron donating groups) and EWGs (electron withdrawing groups) were successfully reacted with NH₄SCN and KSeCN under electrochemical conditions to provide a wide array of mono and bis-chalcogenocyanate-indolizines in 75–94% yields. In addition, 1-substituted imidazo[1,5-a]quinolines were also successfully chalcogenocyanated under the optimized reaction conditions providing a platform for the synthesis of pharmaceutically privileged molecules. By switching the reaction conditions, the developed protocol offers selective synthesis of C-3 thiocyanate and 1,3 bis-thiocyanate indolizines in good to excellent yields under catalyst-free conditions. On the basis of control experiments and cyclic voltammetry data, a plausible reaction pathway is also presented.