Green synthesis of 5-arylidene-2,4-thiazolidinedione, 5-benzylidene rhodanine and dihydrothiophene derivatives catalyzed by hydrated ionic liquid tetrabutylammonium hydroxide in aqueous medium

Abstract

An efficient synthesis of 5-arylidene-2,4-thiazolidinediones and 5-benzylidene rhodanines by the Knoevenagel condensation of 2,4-thiazolidinedione or rhodanine with aromatic aldehydes was studied. It proceeded smoothly in the presence of tetrabutylammonium hydroxide/H ₂O-EtOH to afford the corresponding products in high yields at 50°C. Also, a series of dihydrothiophene derivatives were synthesized via the four-component reaction of aldehyde, malonitrile, 2,4-thiazolidinedione, and piperidine in the presence of Bu₄NOH as a basic ionic liquid in aqueous medium. This new method offers several advantages, such as excellent yields, short reaction times, and simple procedure.

GRAPHICAL ABSTRACT

Keywords:

• rhodanines
• 2,4-thiazolidinediones
• dihydrothiophenes
• ionic liquid