Water-Mediated Multicomponent Reaction: A Facile and Efficient Synthesis of Multisubstituted Thiazolidine-2-thiones

Abstract

A facile, efficient, and green method for the synthesis of multisubstituted thiazolidine-2-thione derivatives via a three-component reaction of amine, carbon disulfide, and α-bromoketone is described. By using water as the reaction medium, the reaction proceeds smoothly to give corresponding products in good to excellent yields.

Key words

green method - synthesis - thiazolidine-2-thione - MCR - heterocyclic compounds

References and Notes

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13

Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 747685.

14

General Procedure
To a solution of amines 1 (0.75 mmol) in H₂O (3 mL), CS₂ (1.5 mmol) and α-bromoketone 2 (0.5 mmol) were added. Subsequently, K₂CO₃ (0.25 mmol) was located to the mixture. After stirring the mixture at r.t. for 1 h, the mixture was extracted with EtOAc (3 × 10 mL), and the combined organic layers were dried overnight with anhyd Na₂SO₄. After the organic solvent was removed, the residue was subjected to silical gel chromatography PE-EtOAc (5:1) as eluent to give pure products.