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Synthesis of new heterocyclic compounds derived from 3-p-tolyl-2-thioxo-1, 3-thiazolidine-4-one and evaluation of their antibacterial activity

Author: 
Ahmed M. Abo-Bakr and Husien H. Abbas-Temirek
Subject Area: 
Physical Sciences and Engineering
Abstract: 

In an effort to discover new biologically active compounds, a series of new heterocyclic compounds have been synthesized from the 3-p-tolyl-2-thioxo-1,3-thiazolidine-4-one (1) and its brominated derivative 5-bromo-3-p-tolyl-2-thioxo-1,3-thiazolidin-4-one (2). Reaction of 1 with 3-benzyloxybenzaldehyde gave the arylidine 3, which either by the reaction with malononitrile gave the pyrano[2,3-d]thiazole 4, or by the reaction with cyanothioacetamide gavethe thiazolo[4,5-b]pyridine 5. Condensation of 1 with ethylformate and cyanothioacetamide gave the thiazolopyridine 6. Treatment of 1 with triethylorthoformate gave the 5-ethoxymethylene derivative 7, and with phosphorous pentachloride and dimethylformamide gave the dimethylaminomethylene derivative 8. Condensation of 1 with isatin, tetrachlorophthalic anhydride and pyromellitic dianhydride afforded the corresponding 9, 10 and 11, respectively. Treatment of the 5-bromo-rhodanine 2 with hydrazine hydrate gave the 5-hyrazinoderivative 12, which reacted with ethoxymethylene malononitrile to give the pyrazole derivative 13. Reaction of 2 with amino-compounds such as, 2-amino-5-phenyl-1,3,4-thiadiazole, 3-amino-5,6-diphenyl-1,2,4-triazine, o-, and p-phenylenediamine afforded 14, 15, 16 and 17, respectively. The reaction of 2 with thioacetamide gave the thiazolothiazole 18. Treatment of 2 with carbon disulfide and p-toluidine afforded the corresponding p-tolyl-dithiocarbamicester 19, which cyclized in ethanol and pipredine to give the thiazolothiazole 20. The chemical structures of the prepared compounds were characterized by their elemental analysis, FT-IR, 1H NMR, 13C NMR and Mass spectra. Investigation of the antibacterial activity of these compounds was done by the paper disc technique. Some of the tested compounds showed high and favorable antibacterial activity.

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