This article is cited in 4 scientific papers (total in 4 papers)
Communications
2-(5-Arylterphenyl-4-yl)quinolines from 2-methylquinoline and 1-(het)aryl-3-phenylprop-2-yn-1-ones in just a one step: A miracle of molecular interplay
Abstract:
2-Methylquinoline reacts with 1-(het)aryl-3-phenylprop-2-yn-1-ones under mild transition metal-free conditions (55–60°C, 20 mol% KOH, H2O, MeCN) to afford 2-{5’-(het)aryl[1,1’ : 3’,1”]terphenyl-4’-yl}quinolines in up to 35% yield. The reaction likely proceeds via the intermediate 1,3-dipole followed by the double nucleophilic vinylation of the methyl group with two molecules of ynone and subsequent elimination of (het)arenecarboxylic acid.
Document Type:
Article
Language: English
Citation:
B. A. Trofimov, K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. V. Vashchenko, “2-(5-Arylterphenyl-4-yl)quinolines from 2-methylquinoline and 1-(het)aryl-3-phenylprop-2-yn-1-ones in just a one step: A miracle of molecular interplay”, Mendeleev Commun., 28:3 (2018), 267–269
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https://www.mathnet.ru/eng/mendc/v28/i3/p267
This publication is cited in the following 4 articles:
Kseniya V. Belyaeva, Lina P. Nikitina, Ludmila A. Oparina, Veronika S. Saliy, Denis N. Tomilin, Anton V. Kuzmin, Andrei V. Afonin, Boris A. Trofimov, “Catalyst-free nucleophilic substitution of hydrogen in quinoline rings by acylethynylpyrroles: stereoselective synthesis of 2-(E-2-acylethenylpyrrolyl)quinolines”, New J. Chem., 48:3 (2024), 1336
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
K. V. Belyaeva, L. P. Nikitina, V. S. Gen', A. V. Afonin, B. A. Trofimov, “Annulation of 1-methylisoquinoline with ethyl esters of 1-aryl-2-oxalylacetylenes: synthesis of functionalized oxazinoisoquinolines”, Russ Chem Bull, 72:11 (2023), 2687
Kseniya V. Belyaeva, Lina P. Nikitina, Andrei V. Afonin, Alexander V. Vashchenko, Boris A. Trofimov, “Synthesis of N-(Z)-acylethenyl-6-hydroxydihydrophenanthridines via the stereoselective functionalization of phenanthridine with acylacetylenes and water”, Tetrahedron Letters, 61:9 (2020), 151553