V. Kozlov, I. Odinets, K. Lyssenko
2005
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0
Influential Citations
16
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Journal
Heteroatom Chemistry
Abstract
Regioselective syntheses of novel 2-(phosphoryl)methylidenethiazolidine-4-ones 3a–c, 5 by the condensation of phosphoryl acetic acid thioamides 2a–c or substituted thioanilide 4 with dimethyl acetylenedicarboxylate are described. N3-unsubstituted thiazolidine-4-ones 3a–c were obtained as E,Z-isomers, while N3-phenyl substituted heterocycle 5 was formed as Z,Z-isomer. The structures of thiazolidin-4-ones 3a-E,Z and 5-Z,Z are characterized by crystal structure determination. According to B3Pw91/6-31G* calculations, the isomers observed in crystals are thermodynamically preferable. In solutions, phosphorylated thiazolidines undergo isomerization (relative to C2 carbon atom of the heterocycle) proceeded by either imine–enamine (N3-unsubstituted compounds 3a–c) or push–pull mechanisms (N3-substituted compound 5). © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:159–222, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20084