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- W2949849069 abstract "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. N 3 ‐unsubstituted thiazolidine‐4‐ones 3a–c were obtained as E,Z‐isomers, while N 3 ‐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 C 2 carbon atom of the heterocycle) proceeded by either imine–enamine ( N 3 ‐unsubstituted compounds 3a–c ) or push–pull mechanisms ( N 3 ‐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" @default.
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- W2949849069 date "2005-01-01" @default.
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- W2949849069 title "Regioselective synthesis, structure and behavior in solutions of novel phosphorylated thiazolidin-4-ones" @default.
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- W2949849069 doi "https://doi.org/10.1002/hc.20084" @default.
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