Abstract:
Reactions between 3-phenyl-2-propynenitrile, secondary phosphine oxides and pyridinoids have been implemented and studied. Pyridine and isoquinoline react with propynenitrile and phosphine oxides at room temperature according to the N-vinylation/C-phosphorylation scheme to afford (Z)-N-(2-cyano-1-phenyl)ethenyl phosphoryl-1,4-dihydropyridines or -1,2-dihydroiso quinolines. In the case of pyridine on heating (80−85∘C), the reaction gives 4-phosphorylpyridines (SHNAr reaction) and 3-phenyl-acrylonitrile oligomers.
Citation:
P. A. Volkov, N. K. Gusarova, K. O. Khrapova, A. A. Telezhkin, A. I. Albanov, S. F. Vasilevskii, B. A. Trofimov, “A mechanistic insight into the chemoselectivity of the reaction between 3-phenyl-2-propynenitrile, secondary phosphine oxides and pyridinoids”, Mendeleev Commun., 31:5 (2021), 670–672
\Bibitem{VolGusKhr21}
\by P.~A.~Volkov, N.~K.~Gusarova, K.~O.~Khrapova, A.~A.~Telezhkin, A.~I.~Albanov, S.~F.~Vasilevskii, B.~A.~Trofimov
\paper A mechanistic insight into the chemoselectivity of the reaction between 3-phenyl-2-propynenitrile, secondary phosphine oxides and pyridinoids
\jour Mendeleev Commun.
\yr 2021
\vol 31
\issue 5
\pages 670--672
\mathnet{http://mi.mathnet.ru/mendc1018}
\crossref{https://doi.org/10.1016/j.mencom.2021.09.026}
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https://www.mathnet.ru/eng/mendc1018
https://www.mathnet.ru/eng/mendc/v31/i5/p670
This publication is cited in the following 7 articles:
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A. A Telezhkin, P. A Volkov, K. O Khrapova, “Nucleophilic substitution of hydrogen in pyridine and its derivatives by organophosphorus nucleophiles in the presence of electron-deficient acetylenes”, Žurnal organičeskoj himii, 59:10 (2023), 1269
P. A. Volkov, K. O. Khrapova, A. A. Telezhkin, A. I. Albanov, K. A. Apartsin, B. A. Trofimov, “SNHAr Reaction of Pyridines with Bis(polyfluoroalkyl)phosphonates Assisted by Electron-Deficient Acetylenes”, Russ J Gen Chem, 92:9 (2022), 1712
Boris A. Trofimov, Pavel A. Volkov, Anton A. Telezhkin, “Electron-Deficient Acetylenes as Three-Modal Adjuvants in SNH Reaction of Pyridinoids with Phosphorus Nucleophiles”, Molecules, 26:22 (2021), 6824
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