This article is cited in 11 scientific papers (total in 11 papers)
Communications
Structural effect in the reductive vinylation/phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides: protonation vs. zwitterion generation
Abstract:
The non-catalyzed reaction of 2- and 3-substituted pyridines with alkyl propiolates and secondary phosphine chalcogenides (50–52°C, MeCN) produces stereo-, regio- and chemoselectively 1-[(E)-2-(alkoxycarbonyl)ethenyl]-4-chalcogenophosphoryl- 1,4-dihydropyridines in 57–90% yields, the adducts of pyridines with alkyl propiolates being the zwitterionic intermediates. 4-Methylpyridine mainly catalyzes nucleophilic addition of secondary phosphine chalcogenides to alkyl propiolates.
Citation:
N. K. Gusarova, P. A. Volkov, N. I. Ivanova, K. O. Khrapova, A. A. Telezhkin, A. I. Albanov, B. A. Trofimov, “Structural effect in the reductive vinylation/phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides: protonation vs. zwitterion generation”, Mendeleev Commun., 27:6 (2017), 553–555
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This publication is cited in the following 11 articles:
V. N. Charushin, E. V. Verbitskiy, O. N. Chupakhin, D. V. Vorobyeva, P. S. Gribanov, S. N. Osipov, A. V. Ivanov, S. V. Martynovskaya, E. F. Sagitova, V. D. Dyachenko, I. V. Dyachenko, S. G. Krivokolylsko, V. V. Dotsenko, A. V. Aksenov, D. A. Aksenov, N. A. Aksenov, A. A. Larin, L. L. Fershtat, V. M. Muzalevskiy, V. G. Nenajdenko, A. V. Gulevskaya, A. F. Pozharskii, E. A. Filatova, K. V. Belyaeva, B. A. Trofimov, I. A. Balova, N. A. Danilkina, A. I. Govdi, A. S. Tikhomirov, A. E. Shchekotikhin, M. S. Novikov, N. V. Rostovskii, A. F. Khlebnikov, Yu. N. Klimochkin, M. V. Leonova, I. M. Tkachenko, V. A.-o. Mamedov, V. L. Mamedova, N. A. Zhukova, V. E. Semenov, O. G. Sinyashin, O. V. Borshchev, Yu. N. Luponosov, S. A. Ponomarenko, A. S. Fisyuk, A. S. Kostyuchenko, V. G. Ilkin, T. V. Beryozkina, V. A. Bakulev, A. S. Gazizov, A. A. Zagidullin, A. A. Karasik, M. E. Kukushkin, E. K. Beloglazkina, N. E. Golantsov, A. A. Festa, L. G. Voskresenskii, V. S. Moshkin, E. M. Buev, V. Ya. Sosnovskikh, I, “The chemistry of heterocycles in the 21st century”, Russian Chem. Reviews, 93:7 (2024), RCR5125
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
Dmitry V. Moiseev, “Phospha-Mannich reactions of phosphinous acids R
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P–OH and their derivatives”, Phosphorus, Sulfur, and Silicon and the Related Elements, 198:11 (2023), 867
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
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
N. K. Gusarova, B. A. Trofimov, “Organophosphorus chemistry based on elemental phosphorus: advances and horizons”, Russian Chem. Reviews, 89:2 (2020), 225–249
P. A. Volkov, A. A. Telezhkin, N. I. Ivanova, K. O. Khrapova, A. I. Albanov, N. K. Gusarova, B. A. Trofimov, “Three-Component Reaction of 4-Methylpyridine with Alkyl Propiolates and Secondary Phosphine Chalcogenides”, Russ J Gen Chem, 88:5 (2018), 912
Boris A. Trofimov, Pavel A. Volkov, Kseniya O. Khrapova, Anton A. Telezhkin, Nina I. Ivanova, Alexander I. Albanov, Nina K. Gusarova, Oleg N. Chupakhin, “Metal-free site selective cross-coupling of pyridines with secondary phosphine chalcogenides using acylacetylenes as oxidants”, Chem. Commun., 54:27 (2018), 3371
Ch. Zheng, X. Hu, Q. Tao, “Synthesis, structures and magnetic properties of two iron(ii) tris(pyridyl)phosphine sulfide complexes”, Mendeleev Commun., 28:2 (2018), 208–210
S. F. Malysheva, V. A. Kuimov, A. B. Trofimov, N. A. Belogorlova, Yu. I. Litvintsev, A. M. Belogolova, N. K. Gusarova, B. A. Trofimov, “2-Halopyridines in the triple reaction in the Pn/KOH/DMSO system to form tri(2-pyridyl)phosphine: Experimental and quantum-chemical dissimilarities”, Mendeleev Commun., 28:5 (2018), 472–474
V. K. Brel, “1,4-Unsubstituted 2-phosphorylated vinylacetylenes as valuable phosphorus-containing dipolarophiles”, Mendeleev Commun., 28:6 (2018), 653–654
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