Аннотация:
The new multicomponent reaction comprises the triethylamine catalyzed assembling of salicylaldehydes, 2-aminoprop- 1-ene-1,1,3-tricarbonitrile and 3-methyl-2-pyrazolin-5-one in small amount of propanol, which affords substituted 2,4-diamino-5-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitriles in 63–98% yields. This process is in agreement with PASE principles and opens the way to new chromeno[2,3-b]pyridine scaffold containing 3-methyl-2-pyrazolin-5-one fragment, which is promising for various biomedical applications.
Образец цитирования:
M. N. Elinson, A. N. Vereshchagin, Yu. E. Anisina, A. S. Goloveshkin, I. E. Ushakov, M. P. Egorov, “PASE facile and efficient multicomponent approach to the new type of 5-C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine scaffold”, Mendeleev Commun., 28:4 (2018), 372–374
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc1770
https://www.mathnet.ru/rus/mendc/v28/i4/p372
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
Younesse Ait Elmachkouri, Ezaddine Irrou, Hanae El Monfalouti, Ahmed Mazzah, Tuncer Hökelek, Joel T. Mague, Mohamed Labd Taha, Nada Kheira Sebbar, “Crystal structure, Hirshfeld surface analysis, crystal voids, interaction energy calculations and energy frameworks and DFT calculations of ethyl 2-cyano-3-(3-hydroxy-5-methyl-1H-pyrazol-4-yl)-3-phenylpropanoate”, Acta Crystallogr E Cryst Commun, 80:2 (2024), 240
Lokesh Kumar S, Sumaiya Tabassum, Sagar K S, Santhosh Govindaraju, “A Mini Review on the Multicomponent Synthesis of Pyridine Derivatives”, ChemistrySelect, 7:47 (2022)
Fedor V. Ryzhkov, Michail N. Elinson, Yuliya E. Ryzhkova, Anatoly N. Vereshchagin, Victor A. Korolev, Mikhail P. Egorov, “Pseudo‐four‐component synthesis and in silico studies of 5‐(5‐hydroxy‐3‐methyl‐1H‐pyrazol‐4‐yl)‐substituted 5H‐chromeno[2,3‐b]pyridines”, Journal of Heterocyclic Chem, 58:3 (2021), 793
Lakha V. Chopda, Pragnesh N. Dave, “12-Phosphomolybdic acid H3[PMo12O40] over natural bentonite as a heterogeneous catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones”, Results in Chemistry, 3 (2021), 100169
М. Н. Элинсон, Ю. Е. Рыжкова, Ф. В. Рыжков, “Мультикомпонентный дизайн хромено[2,3-b]пиридиновых систем”, Усп. хим., 90:1 (2021), 94–115; M. N. Elinson, Yu. E. Ryzhkova, F. V. Ryzhkov, “Multicomponent design of chromeno[2,3-b]pyridine systems”, Russian Chem. Reviews, 90:1 (2021), 94–115
Fedor V. Ryzhkov, Yuliya E. Ryzhkova, Michail N. Elinson, Stepan V. Vorobyev, Artem N. Fakhrutdinov, Anatoly N. Vereshchagin, Mikhail P. Egorov, “Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-b]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism”, Molecules, 25:11 (2020), 2573
Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Anisina, Stepan K. Krymov, Artem N. Fakhrutdinov, Alexander S. Goloveshkin, Mikhail P. Egorov, “Pot, atom and step economic (PASE) assembly of salicylaldehydes, malononitrile dimer and 4-hydroxypyridine-2(1H)-ones into medicinally relevant 5H-chromeno[2,3-b]pyridine scaffold”, Mol Divers, 24:3 (2020), 617
Majid Heravi, Vahideh Zadsirjan, Recent Advances in Applications of Name Reactions in Multicomponent Reactions, 2020, 139
Fedor V. Ryzhkov, Yuliya E. Ryzhkova, Michail N. Elinson, Anatoly N. Vereshchagin, Victor A. Korolev, Mikhail P. Egorov, “Quadruple Bond Forming Multicomponent Approach to 5-(3-chromenyl)-5H-chromeno[2,3-b]pyridines and Its Interaction with the Neuropeptide Y1 Receptor”, Chem Heterocycl Comp, 56:12 (2020), 1560
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
M. N. Elinson, A. N. Vereshchagin, Yu. E. Ryzhkova, S. K. Krymov, N. A. Leonova, A. S. Goloveshkin, M. P. Egorov, “Electrocatalytic one-pot multicomponent assembly of aldehydes, 2,4-dihydro-3H-pyrazol-3-ones and kojic acid”, Mendeleev Commun., 30:2 (2020), 223–225
Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Anisina, Stepan K. Krymov, Artem N. Fakhrutdinov, Mikhail P. Egorov, “Selective multicomponent 'one-pot' approach to the new 5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)chromeno[2,3-b]pyridine scaffold in pyridine–ethanol catalyst/solvent system”, Monatsh Chem, 150:6 (2019), 1073
Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Anisina, Artem N. Fakhrutdinov, Alexander S. Goloveshkin, Mikhail P. Egorov, “Pot‐, Atom‐ and Step‐Economic (PASE) Multicomponent Approach to the 5‐(Dialkylphosphonate)‐Substituted 2,4‐Diamino‐5H‐chromeno[2,3‐b]pyridine Scaffold”, Eur J Org Chem, 2019:26 (2019), 4171
I. G. Mamedov, V. N. Khrustalev, P. V. Dorovatovskii, F. N. Naghiev, A. M. Maharramov, “Efficient synthesis of new tricyclic pyrano[3,2-c]pyridine derivatives”, Mendeleev Commun., 29:2 (2019), 232–233
M. N. Elinson, A. N. Vereshchagin, Yu. E. Anisina, S. K. Krymov, A. N. Fakhrutdinov, M. P. Egorov, “Multicomponent assembling of salicylaldehydes, kojic acid and malonic acid derivatives”, Mendeleev Commun., 29:5 (2019), 581–583
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