One-pot regio- and stereoselective synthesis of tertiary phosphine chalcogenides with (E)-N-ethenyl-1,2-dihydroquinoline functionalities

[Display omitted] •One-pot synthesis of functional tertiary phosphine chalcogenides has been reported.•Three-component reaction between R2P(X)H, quinolines, and acetylenes.•The method is stereo- and regioselective: 1,2-dihydroquinolines are prepared.•With isoquinoline the reaction proceeds faster an...

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Bibliographic Details
Published in:Tetrahedron letters 2016-08, Vol.57 (33), p.3776-3780
Main Authors: Gusarova, Nina K., Volkov, Pavel A., Ivanova, Nina I., Khrapova, Kseniya O., Albanov, Alexander I., Afonin, Andrei V., Borodina, Tatyana N., Trofimov, Boris A.
Format: Article
Language:English
Subjects:
Electron-deficient alkynes
One-pot, three-component, regio- and stereoselective reaction
Quinolines
Secondary phosphine chalcogenides
Tertiary phosphine chalcogenides with (E)-N-ethenyl-1,2-dihydroquinoline functionalities
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Summary:[Display omitted] •One-pot synthesis of functional tertiary phosphine chalcogenides has been reported.•Three-component reaction between R2P(X)H, quinolines, and acetylenes.•The method is stereo- and regioselective: 1,2-dihydroquinolines are prepared.•With isoquinoline the reaction proceeds faster and more efficiently. The three-component reaction between secondary phosphine chalcogenides, quinoline or isoquinoline and alkyl propiolates or acetylene dicarboxylates occurs under mild conditions, without a catalyst, to regio- and stereoselectively afford tertiary phosphine chalcogenides with (E)-N-ethenyl-1,2-dihydroquinoline functionalities in up to 93% yield.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.07.024