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Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023

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Synthesis of Novel Fluorinated 5-Benzylidine-3-ethyl-2-(2,3,4-trifluorophenylimino)thiazolidin-4-one Derivatives using Knoevenagel Reaction and Evaluation of their in vitro Antimicrobial Potentials

https://doi.org/10.14233/ajchem.2023.28052
S.D. Kadam
School of Science, Navrachana University, Vasana-Bhayli Road-391410, India
https://orcid.org/0000-0003-4213-4165
D. Mammen
School of Science, Navrachana University, Vasana-Bhayli Road-391410, India
https://orcid.org/0000-0002-8115-302X
D.S. Kadam
Organic Chemistry Research Laboratory, Maharashtra Udayagiri Mahavidyalaya, Udgir-413517, India
https://orcid.org/0000-0002-2639-3506
S.G. Patil
Organic Chemistry Research Laboratory, Maharashtra Udayagiri Mahavidyalaya, Udgir-413517, India
https://orcid.org/0000-0002-8036-7683
R.R. Bagul
Department of Chemistry, Career Point University, National Highway 52, Kota-325003, India
https://orcid.org/0009-0007-5972-4539
A. Doshi
School of Science, Navrachana University, Vasana-Bhayli Road-391410, India
https://orcid.org/0000-0003-4886-1216
F. Patel
School of Science, Navrachana University, Vasana-Bhayli Road-391410, India
https://orcid.org/0000-0002-7953-2442

Corresponding Author(s) : D. Mammen

drdenni.mammen@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023

Abstract

A series of novel 5-benzylidine-3-ethyl-2-(2,3,4-trifluoro-phenylimino)-thiazolidin-4-one derivatives were synthesized by Knoevenagel reaction using both conventional as well as non-conventional methods on the synthesized iminothiazolidinone core. The results of an ultrasonic Knoevenagel reaction showed that it was more efficient than the traditional method in terms of yield and reaction time. The compounds were characterized using 1H, 19F and 13C NMR spectra, supported by mass spectrometric and infrared spectroscopic data. The stereochemistry of the final compounds was confirmed using 2D NOESY NMR experiment. The in vitro antibacterial potential of the synthesized benzylidine derivatives were also evaluated. Compounds having trifluoromethyl group on benzylidine moiety were observed to be the most active against the tested bacterial strains as compared to the rest of the compounds.

Keywords

Thiazolidin-4-ones Ultrasonic waves Knoevenagel reaction Antibacterial activity
Kadam, S., Mammen, D., Kadam, D., Patil, S., Bagul, R., Doshi, A., & Patel, F. (2023). Synthesis of Novel Fluorinated 5-Benzylidine-3-ethyl-2-(2,3,4-trifluorophenylimino)thiazolidin-4-one Derivatives using Knoevenagel Reaction and Evaluation of their in vitro Antimicrobial Potentials. Asian Journal of Chemistry, 35(8), 1884–1890. https://doi.org/10.14233/ajchem.2023.28052
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