Green synthesis of 5-arylidene-2,4-thiazolidinedione, 5-benzylidene rhodanine and dihydrothiophene derivatives catalyzed by hydrated ionic liquid tetrabutylammonium hydroxide in aqueous medium |
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Authors: | Ardeshir Khazaei Maryam Safaei Hossein Ahmadian |
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Affiliation: | 1. Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 6517838683, Hamedan, Iran;2. Department of Chemistry, Payame Noor University, 19395-4697 Tehran, Iran |
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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. |
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Keywords: | rhodanines 2 4-thiazolidinediones dihydrothiophenes ionic liquid |
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