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Novel thiopyrano[2,3-d]thiazole derivatives were synthesized from 5-arylidene-4-thioxo-2-thiazolidinones and 2(5H)furanone in 62–79% yields via hetero-Diels–Alder reactions and related acylation-based tandem processes. The reaction of 5-(4-fluorophenyl)-4-thioxo-2-thiazolidinone with 2(5H)furanone was studied by DFT at the M06-2X/6-31+G(d,p) level. The stereo- and regioselectivities of cycloaddition were confirmed by NMR spectra and single-crystal X-ray diffraction analyses.

The screening of the in vitro anticancer activity of the synthesized compounds shows that compounds (IVa), (VIIIb), (VIIId) are the most active compounds against different cell lines.

A new approach to the synthesis of new heterocyclic compounds with triazine and 4-thiazolidone fragments in one molecule is developed. The synthesis methods comprise [2+3]-cyclocondensation reactions essential in the preparative synthesis of 4-thiazolidone derivatives. The reactions of S,N-nucleophiles with C2-cyclization agents for the synthesis of a number of biologically active 2-triazin-4-thiazolidones were investigated. The interaction of thiosemicarbazone of sym-triazine with derivatives of α-halogencarboxylic acids and maleic anhydride resulted in correspondent (2-[2-(4,6-dichloro-1,3,5-triazin-2-yl)hydrazino]-5-(3,4,5- R-p-phenyl-methyliden)-1,3-thiazol-4-ones obtained in the one-step synthesis. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:392–396, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20631