Three-Component Reaction of 4-Methylpyridine with Alkyl Propiolates and Secondary Phosphine Chalcogenides

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-C 2 - phosphoryl-1,2-dihydropyridines [when using bis(2-phenylethyl)phosphine oxide] or ( E )- N -eth...

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Bibliographic Details
Published in:Russian journal of general chemistry 2018-05, Vol.88 (5), p.912-918
Main Authors: Volkov, P. A., Telezhkin, A. A., Ivanova, N. I., Khrapova, K. O., Albanov, A. I., Gusarova, N. K., Trofimov, B. A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Phosphine oxide
Phosphorylation
Pyridine
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Summary: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-C 2 - phosphoryl-1,2-dihydropyridines [when using bis(2-phenylethyl)phosphine oxide] or ( E )- N -ethenyl-C 4 - 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.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363218050122