Imidazole-Based Bronsted Acidic Surfactant: A Novel Regioselective Catalytic System for Making of 2-Aryl-1,2-Dihydrothiazolo[3,2-b][1, 2, 4]Triazol-6(5H)-Ones

Abstract

We have synthesized a novel bronsted acidic surfactant, 3-methyl-1-sulfonic acid imidazolium dioctyl sulfosuccinate [MSIM]+ [DOSS]−. We explored catalytic activity of [MSIM]+ [DOSS]− for regioselective synthesis of novel class of thiazolotriazolones from the reaction of aldehydes/ketones, thiosemicarbazide and ethylbromo acetate in aqueous medium at room temperature. The regio-selectivity was confirmed by DFT and IR frequency calculations. The present methodology offers a feasible approach for swift access to collection of extremely pure products with wide substrate scope having several advantages such as excellent yields, short reaction time, easy work-up procedure for isolation of product and use of surfactant as eco-friendly catalyst, use of water as an universal solvent and novelty in synthesis of surfactant [MSIM]+ [DOSS]− as well as investigation of regioselective synthesis of novel class of thiazolotriazolones.