A safe and new strategy for N-arylation of 2,4-thiazolidinediones via microwave irradiation using base catalyst K2CO3 in DMF

Abstract

Green efforts towards the awareness of green chemistry as an alternative to the existing conventional methods for organic synthesis and providing new tools, knowledge, and design of organic synthesis will contribute to the social economy in protecting the environment and health. To avoid the environmental hazards generated by organic synthesis, microwave technology plays a key role in protecting the planet from the consequences of chemicals and solvents used in the synthesis. A rapid and green method for the synthesis of novel N-thiazolidine-2,4-dione derivatives 3(a–j) from thiazolidine-2,4-diones, substituted benzyl halide, and sodium bicarbonate as a base catalyst in dimethylformamide (DMF) solvent is reported. The N-arylation of imides is a significant reaction in the synthesis of biologically active thiazolidine-2,4-dione derivatives. In this study, efficient base catalyst K₂CO₃ in DMF was used to catalyze the N-arylation of thiazolidinediones with aryl halides under microwave irradiation. The attractive advantages of this process include mild reaction conditions, environment-friendly procedure, short reaction time, easy isolation of target products, and excellent yields (73–89%). The structures were confirmed by FT-IR, ¹HNMR, ¹³C NMR, and mass spectrometry analysis.