Аннотация:
The Knövenagel–Michael–Mannich cascade reaction of aromatic aldehyde (3 equiv.), malononitrile (2 equiv.) and ammonium acetate or aqueous ammonia provides convenient stereoselective access to cis,cis-2,4,6-triaryl-3,3,5,5-tetracyanopiperidines in 62–94% yields. Six new bonds form as a result of the domino process, ammonium acetate serving as a nitrogen source.
Образец цитирования:
A. N. Vereshchagin, K. A. Karpenko, M. N. Elinson, E. O. Dorofeeva, A. S. Goloveshkin, M. P. Egorov, “Pseudo six-component stereoselective synthesis of 2,4,6-triaryl-3,3,5,5-tetracyanopiperidines”, Mendeleev Commun., 28:4 (2018), 384–386
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc1774
https://www.mathnet.ru/rus/mendc/v28/i4/p384
Эта публикация цитируется в следующих 16 статьяx:
Fábio Pedroso de Lima, Marta Costa, Ana Sousa, Maria Fernanda Proença, “The Chromenopyridine Scaffold: A Privileged Platform in Drug Design”, Molecules, 29:13 (2024), 3004
Julio C. Flores-Reyes, Vanesa del C. Cotlame-Salinas, Ilich A. Ibarra, Eduardo González-Zamora, Alejandro Islas-Jácome, “Pseudo-multicomponent reactions”, RSC Adv., 13:24 (2023), 16091
Nikita A. Frolov, Anatoly N. Vereshchagin, “Piperidine Derivatives: Recent Advances in Synthesis and Pharmacological Applications”, IJMS, 24:3 (2023), 2937
K. A. Karpenko, T. M. Iliyasov, A. N. Fakhrutdinov, A. S. Akulinin, M. N. Elinson, A. N. Vereshchagin, “Study on formation mechanism of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylic esters”, Russ Chem Bull, 71:6 (2022), 1278
Carolina S. Marques, Elisabete P. Carreiro, António P. S. Teixeira, Heterocycles, 2022, 215
Anatoly N. Vereshchagin, Taigib M. Iliyasov, Kirill A. Karpenko, Radmir N. Akchurin, Mikhail E. Minyaev, “Tetrahydropyridines' Stereoselective Formation, How Lockdown Assisted in the Identification of the Features of Its Mechanism”, Molecules, 27:14 (2022), 4367
T. M. Iliyasov, K. A. Karpenko, A. D. Vinokurov, A. N. Fakhrutdinov, A. A. Tyutin, M. N. Elinson, A. N. Vereshchagin, “Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers”, Mendeleev Commun., 32:5 (2022), 629–631
Anatoly N. Vereshchagin, Taygib M. Iliyasov, Kirill A. Karpenko, Vladimir A. Smirnov, Ivan E. Ushakov, Michail N. Elinson, “Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines”, Chem Heterocycl Comp, 57:9 (2021), 929
Anatoly N. Vereshchagin, Kirill A. Karpenko, Michail N. Elinson, Alexandra P. Minaeva, Alexander S. Goloveshkin, Karl A. Hansford, Mikhail P. Egorov, “One-pot five-component high diastereoselective synthesis of polysubstituted 2-piperidinones from aromatic aldehydes, nitriles, dialkyl malonates and ammonium acetate”, Mol Divers, 24:4 (2020), 1327
Fedor V. Ryzhkov, Michail N. Elinson, Yuliya E. Ryzhkova, Anatoly N. Vereshchagin, Alexander S. Goloveshkin, Mikhail P. Egorov, “Stereoselective domino assembling of five molecules: one-pot approach to (2 ′ R * ,3S * ,4 ′ R * )-2 ′ ,4 ′ -diaryl-1 ′ ,4 ′ -dihydro-2 ′ H-spiro[indoline-3,3 ′ -pyridines]”, Comptes Rendus. Chimie, 23:2 (2020), 159
Anatoly N. Vereshchagin, Kirill A. Karpenko, Michail N. Elinson, Alexander S. Goloveshkin, Evgeniya O. Dorofeeva, Mikhail P. Egorov, “Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers”, Res Chem Intermed, 46:2 (2020), 1183
В. Г. Ненайденко, “На пути к молекулярной сложности. Многокомпонентные реакции, включающие пять и более компонентов”, Усп. хим., 89:11 (2020), 1274–1336; V. G. Nenajdenko, “Access to molecular complexity. Multicomponent reactions involving five or more components”, Russian Chem. Reviews, 89:11 (2020), 1274–1336
O. I. Afanasyev, I. R. Cherkashchenko, A. Kuznetsov, F. Kliuev, S. Semenov, O. Chusova, G. Denisov, D. A. Chusov, “Alkyl formates as reagents for reductive amination of carbonyl compounds”, Mendeleev Commun., 30:1 (2020), 112–113
M. N. Elinson, A. N. Vereshchagin, Yu. E. Anisina, N. A. Leonova, M. P. Egorov, “On water noncatalytic tandem Knoevenagel–Michael reaction of aldehydes, N,N'-dimethylbarbituric acid and cyclohexane-1,3-diones”, Mendeleev Commun., 30:1 (2020), 15–17
A. N. Vereshchagin, K. A. Karpenko, M. N. Elinson, S. V. Gorbunov, Yu. E. Anisina, M. P. Egorov, “Stereoselective multicomponent synthesis of (2RS,6SR)-2,6-diaryl-3,3,5,5-tetracyanopiperidines”, Russ Chem Bull, 67:8 (2018), 1534
A. N. Vereshchagin, K. A. Karpenko, T. M. Iliyasov, M. N. Elinson, E. O. Dorofeeva, A. N. Fakhrutdinov, M. P. Egorov, “Diastereoselective multicomponent synthesis of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylates”, Russ Chem Bull, 67:11 (2018), 2049
Обратная связь: