Three-Component Reaction of 4-Methylpyridine with Alkyl Propiolates and Secondary Phosphine Chalcogenides
- Authors: Volkov P.A.1, Telezhkin A.A.1, Ivanova N.I.1, Khrapova K.O.1, Albanov A.I.1, Gusarova N.K.1, Trofimov B.A.1
-
Affiliations:
- Favorskii Irkutsk Institute of Chemistry, Siberian Branch
- Issue: Vol 88, No 5 (2018)
- Pages: 912-918
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/222180
- DOI: https://doi.org/10.1134/S1070363218050122
- ID: 222180
Cite item
Abstract
The reaction between 4-methylpyridine, alkyl propiolates, and secondary phosphine oxides proceeded as N-vinylation-C-phosphorylation with stereo- and regioselective formation of (E)-N-ethenyl-C2- phosphoryl-1,2-dihydropyridines [when using bis(2-phenylethyl)phosphine oxide] or (E)-N-ethenyl-C4- phosphoryl-1,4-dihydropyridines (when using diphenylphosphine oxide). The process occurred at 60–62°C within 3 h to give functional dihydropyridines in 40–82% yield. Under similar conditions, bis(2-phenylethyl) phosphine sulfide and selenide reacted with alkyl propiolates preferably by nucleophilic PH-monoaddition at the triple bond.
About the authors
P. A. Volkov
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: boris_trofimov@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
A. A. Telezhkin
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: boris_trofimov@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
N. I. Ivanova
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: boris_trofimov@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
K. O. Khrapova
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: boris_trofimov@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
A. I. Albanov
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: boris_trofimov@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
N. K. Gusarova
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: boris_trofimov@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
B. A. Trofimov
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Author for correspondence.
Email: boris_trofimov@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
![](/img/style/loading.gif)