Three-Component Reaction of 4-Methylpyridine with Alkyl Propiolates and Secondary Phosphine Chalcogenides
Publication type: Journal Article
Publication date: 2018-05-01
scimago Q4
wos Q4
SJR: 0.179
CiteScore: 1.4
Impact factor: 0.8
ISSN: 10703632, 16083350
General Chemistry
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.
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Volkov P. A. et al. Three-Component Reaction of 4-Methylpyridine with Alkyl Propiolates and Secondary Phosphine Chalcogenides // Russian Journal of General Chemistry. 2018. Vol. 88. No. 5. pp. 912-918.
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Volkov P. A., A. A. T., Ivanova N., Khrapova K. O., Albanov A. I., Gusarova N. K., Trofimov B. A. Three-Component Reaction of 4-Methylpyridine with Alkyl Propiolates and Secondary Phosphine Chalcogenides // Russian Journal of General Chemistry. 2018. Vol. 88. No. 5. pp. 912-918.
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RIS
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TY - JOUR
DO - 10.1134/s1070363218050122
UR - https://doi.org/10.1134/s1070363218050122
TI - Three-Component Reaction of 4-Methylpyridine with Alkyl Propiolates and Secondary Phosphine Chalcogenides
T2 - Russian Journal of General Chemistry
AU - Volkov, P. A.
AU - A. A., Telezhkin
AU - Ivanova, N.I.
AU - Khrapova, K O
AU - Albanov, A I
AU - Gusarova, N K
AU - Trofimov, B. A.
PY - 2018
DA - 2018/05/01
PB - Pleiades Publishing
SP - 912-918
IS - 5
VL - 88
SN - 1070-3632
SN - 1608-3350
ER -
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BibTex (up to 50 authors)
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@article{2018_Volkov,
author = {P. A. Volkov and Telezhkin A. A. and N.I. Ivanova and K O Khrapova and A I Albanov and N K Gusarova and B. A. Trofimov},
title = {Three-Component Reaction of 4-Methylpyridine with Alkyl Propiolates and Secondary Phosphine Chalcogenides},
journal = {Russian Journal of General Chemistry},
year = {2018},
volume = {88},
publisher = {Pleiades Publishing},
month = {may},
url = {https://doi.org/10.1134/s1070363218050122},
number = {5},
pages = {912--918},
doi = {10.1134/s1070363218050122}
}
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MLA
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Volkov, P. A., et al. “Three-Component Reaction of 4-Methylpyridine with Alkyl Propiolates and Secondary Phosphine Chalcogenides.” Russian Journal of General Chemistry, vol. 88, no. 5, May. 2018, pp. 912-918. https://doi.org/10.1134/s1070363218050122.