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Microwave Assisted Highly Efficient Synthesis of Rhodanine and -2, 4- Thiazolidinedione Derivatives Under Solvent Free Conditions

[ Vol. 5 , Issue. 3 ]

Author(s):

Alireza Khajeh-Amiri*, Naser Foroughifar, Farkhondeh Hassannejad, Bahareh Esfahani and Akram Zanganeh   Pages 215 - 224 ( 10 )

Abstract:


Background: In the present study, we performed according to green chemistry’s standards, an easy and very efficient one-pot synthesis of2-thioxo-1,3-thiazolidin-4-one(rhodanine) and thiazolidine-2,4-dione (TZD) derivatives via Knoevenagel condensation of various aldehydes with rhodanine/ thiazolidine-2,4-dione in the presence of only 15 mole% of deep eutectic solvents (DESs) -choline chloride/urea- propionate and microwave radiation under solvent-free conditions.

Method: Twenty compounds were synthesized under thermal and microwave conditions and the yields of synthesized compounds were 77-90% and 81-95%, respectively. The IR spectra were obtained on a PerkineElmer FT-IR spectrophotometer using KBr disks.1H NMR and 13C NMR of products were registered Bruker 500 spectrometer and chemical shifts are expressed as d (ppm) with tetramethylsilane (TMS) as an internal standard in DMSO-d6 as a solvent. The purity of synthesized compounds was checked by chromatography and UV light (254 nm) was used for visualization.

Result: A range of rhodanine and -2, 4-thiazolidinedione derivatives were synthesized using ChCl/ urea catalyst under solvent -free conditions at 80°C. Then, the sample derivatives were synthesized under optimum conditions.

Conclusion: The mild reaction conditions, good to excellent yields, easy workup, without the involvement of any harmful solvents/chemicals and easily available substrates, they all facilitated in the preparation of all synthesized compounds.

Keywords:

Deep Eutectic Solvents (DESs), green chemistry, knoevenagel condensation, microwave heating, solvent-free condition.

Affiliation:

Toxin Research Institute, Aja University of Medical Sciences, Tehran, Department of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Comprehensive Research Laboratory, Incubator Center of Aja University of Medical Sciences, Department of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Department of Chemistry, Tehran North Branch, Islamic Azad University, Tehran

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