2- Thioxo-l,3-thiazolidine-4-one

One of the earliest preparations of the 1,2,4-dithiazole (30) was by acid treatment of a concentrated aqueous solution of 2-thioxo-l,3-thiazolidin-4-one ( rhodanic acid ) (1842LA(43)76) or of one of its salts Ac20 with the> ammonium salt gave the /V-acetyl derivative (1873CB902). Thermolysis of 2-phenyl-l,3-tbiazoline-4,5-dio ne leads via loss of CO to thiobenzoylisocyanate, which with sulfur or P4S10 yields a dithiazolinethione (Scheme 4D. 

Atropisomerism in 3-aryl-2-thioxo-l,3-thiazolidin-4-ones 413,3-aryl-2-thioxoimidazolidin-4-one 414, 3-aryl-2-thioxo-l,3-oxazolidin-4-one 415 have attracted much interest. Atropisomerism was monitored by NMR of the AB spectra of the hydrogen in position 5. 5-Substituted derivatives yielded diastereomers. In the case of a high barrier, separation was performed by chromatography on a chiral support. 

An interesting series of N-(2-halogenophenyl) 2-thioxo-l,3-thiazolidin-4-ones 413d, 413b, 413e, and 413f was separated into enantiomers on... 

Jiang S, Tala SR, Lu H et al (2011) Design, synthesis, and biological activity of novel 5-((arylfuran/l//-pyrrol-2-yl)methylene)-2-thioxo-3-(3-(trifluoromethyl)phenyl)thiazolidin-4-ones as HIV-1 fusion inhibitors targeting gp41. J Med Chem 54 572-579... 

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