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.

Graphical Abstract

Keywords:

• Surfactant
• dioctyl sulfosuccinate
• regioselectivity
• thiazole
• DFT calculation

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

One of the authors MVP is thankful to Shivaji University, Kolhapur for providing Golden Jubilee Research Fellowship [Ref No. SU/CUDC/UGK/GJRF/16/2019-20/763] of Department of Industrial Chemistry.