A redox active organodiselenide as an efficacious catalyst for the synthesis of oxygen-containing heterocyclic compounds

Abstract

3,3′-Diselenodipropionic acid (DSePA) is a water-soluble deaminated analogue of selenocystine. Owing to its acidic groups and the redox activity of the diselenide moiety present in it, DSePA was found to serve as an efficacious catalyst in the synthesis of tetrahydrobenzo[b]pyran derivatives through a three-component one-pot condensation reaction under ultrasonic conditions in an aqueous ethanol mixture. A comparative study was conducted to assess the catalytic performance of DSePA and its non-selenium analogue in synthesizing tetrahydrobenzo[b]pyran derivatives. It was observed that reactions catalyzed by DSePA exhibited high yields, ranging from 80 to 95%. The established synthetic protocol was compatible with a diverse array of aromatic aldehydes bearing electron-donating or electron-withdrawing groups, resulting in excellent yields within short reaction times (10–25 minutes). Notable features of this synthetic approach include operational simplicity, the use of an environmentally benign catalyst, mild reaction conditions, high product yields, and expeditious reaction times.