SYNTHESIS OF 3-PYRIDYL SUBSTITUTED 4-THIAZOLIDINONES AS POTENTIAL BIOLOGICALLY ACTIVE COMPOUNDS
DOI:
https://doi.org/10.11603/2312-0967.2017.1.7533Keywords:
synthesis, 4-thiazolidinone, [2 3]-cyclocondensation, Knoevenagel reaction, spectral characteristics.Abstract
The aim of the work. The synthesis of 3-pyridylsubstituted 5-arylidene-4-thiazolidinones as potential biologically active compounds.
Materials and Methods. All starting materials were purchased from commercial sources and used without puri cation. The 1H NMR spectra were recorded on a Varian Gemini 400-MHz instrument. Melting points are uncorrected and were measured in open capillary tubes on a BŰCHI B-545 melting point apparatus.
Results and Discussion. Novel 3-pyridylsubstituted 5-arylidene-2-thioxo-4-thiazolidinones were synthesized using Holmberg method and Knoevenagel reaction. For the synthesis of structurally similar 3-(2-pyridyl)-2.4-thiazolidinediones two-stage approach were proposed. This approach is based on «one-pot» three-component reaction of 1-benzoyl-3-(pyridine-2-yl)-2-thiourea, chloroacetic acid and aromatic aldehyde yielding 5-arylidene-2-benzoylimino-3-(2-pyridyl)-4-thiazolidinones which via acid hydrolysis in high yields form the target products. The structure of synthesized compounds was con rmed by NMR spectroscopy.
Conclusions. A series of novel 3-pyridylsubstituted rhodanine, thiazolidinedione and psudothiohydantoine derivatives were synthesized. The 1H NMR spectra futures con rmed stereoselectivity of Knoevenagel reaction and obtaining of 5-(Z)-arylidene-4-thiazolidinones.
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