Improved Protocol Toward 1,3,4-Oxadiazole-2(3H)-thiones and Scale-up Synthesis in the Presence of SDS as a Micelle Promoted Catalyst

Abstract

Convenient procedure for in situ cyclization of hydrazinecarbodithioate potassium salts to 1,3,4-oxadiazole-2(3H)-thiones under normal phase micellar media catalysis promoted by sodium dodecyl sulfate (SDS) as an anionic surfactant is reported. The main advantage of this procedure is to provide shorter reaction time for the completion of cyclization; scale-up synthesis is possible and the oxadiazoles were obtained in high to excellent yields (87-100%), making the protocol an attractive alternative to the available methods.

Mild and efficient regioselective surfactant catalyzed deacylation of lipophilic 5‐substituted 4‐acyl‐2‐(acylamino)‐Δ2‐1,3,4‐thiadiazolines

“…Moreover, surfactant-catalyzed reactions carried out in aqueous medium or in organic solvents including water phase still maintain their popularity. As a part of our continual work toward the progress of sustainable methods for preparation of valuable compounds with various heterocyclic ring systems [25][26][27][28][29][30][31], we wish to report here a sustainable protocol toward biologically active compounds. In the literature, terpenone and carbohydrate based some natural carbonyl compounds were chosen as starting materials, and chiral Δ 2 -1,3,4-thiadiazoline derivatives with biological activity were synthesized and some mechanistic approaches were discussed [32][33][34][35][36][37][38][39][40].…”