Novel Bicyclic P , S -Heterocycles via Stereoselective hetero -Diels-Alder Reactions of Thiochalcones with 1-Phenyl-4 H -phosphinin-4-one 1-Oxide

Thiochalcones undergo cycloaddition reactions in THF solution at 60 °C with the synthetically unexplored 1-phenyl-4 -phosphinin-4-one 1-oxide in a highly regio- and stereoselective manner, yielding hitherto unknown bicyclic , -heterocycles containing fused thiopyran and phosphinine rings. The stereo...

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Bibliographic Details
Published inMolecules (Basel, Switzerland) Vol. 29; no. 9
Main Authors Mlostoń, Grzegorz, Urbaniak, Katarzyna, Palusiak, Marcin, Łastawiecka, Elżbieta, Frynas, Sławomir, Pietrusiewicz, Kazimierz Michał, Heimgartner, Heinz
Format Journal Article
LanguageEnglish
Published Switzerland 28.04.2024
Subjects
P-heterocycles
hetero-Diels–Alder reaction
fused P,S-heterocycles
thiochalcones
S-heterocycles
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Summary:Thiochalcones undergo cycloaddition reactions in THF solution at 60 °C with the synthetically unexplored 1-phenyl-4 -phosphinin-4-one 1-oxide in a highly regio- and stereoselective manner, yielding hitherto unknown bicyclic , -heterocycles containing fused thiopyran and phosphinine rings. The stereochemical structures of two of the obtained (4+2)-cycloadducts were unambiguously assigned by means of the X-ray single-crystal analysis. Based on these assignments, a concerted mechanism of the -Diels-Alder reaction via the preferred approach of the heterodiene from the less hindered P=O side of the phosphininone molecule is postulated to explain the established rac-(4 ,8 ,9 ,10 )-configured (4+2)-cycloadducts isolated as major products.
ISSN:1420-3049