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A novel green on-water multicomponent approach for the synthesis of pyrrolo[2,3-d]pyrimidines was developed based on the multicomponent reaction of arylglyoxals, barbituric acids, and 6-aminopyrimidine-2,4(1H,3H)-diones. The studied non-catalytic process includes Knoevenagel condensation, Michael addition, and intramolecular heterocyclization. The structure of one of the pyrrolo[2,3-d]pyrimidine derivatives was determined by 2D NMR spectroscopy.
Yuliya E. Ryzhkova; Artem N. Fakhrutdinov; Michail N. Elinson. Green on-water multicomponent approach for the synthesis of pyrrolo[2,3-d]pyrimidines. Tetrahedron Letters 2021, 153336 .
AMA StyleYuliya E. Ryzhkova, Artem N. Fakhrutdinov, Michail N. Elinson. Green on-water multicomponent approach for the synthesis of pyrrolo[2,3-d]pyrimidines. Tetrahedron Letters. 2021; ():153336.
Chicago/Turabian StyleYuliya E. Ryzhkova; Artem N. Fakhrutdinov; Michail N. Elinson. 2021. "Green on-water multicomponent approach for the synthesis of pyrrolo[2,3-d]pyrimidines." Tetrahedron Letters , no. : 153336.
The ammonium salts of many drugs have significantly improved the solubility and, accordingly, the bioavailability of medicinal substances in the human body. 5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-5H-chromeno[2,3-b]pyridines are potential NPY1R ligands, which are attractive for antiobesity treatment. Ammonium salts of 5H-chromeno[2,3-b]pyridines were previously unknown. In this communication, it was found that the four-component reaction of salicylaldehyde, 2-aminoprop-1-ene-1,1,3-tricarbonitrile, 4-Hydroxy-2H-chromen-2-one and amines results in the formation of ammonium salts of 5-(3-chromenyl)-5H-chromeno[2,3-b]pyridines. The structure of these previously unknown compounds was confirmed by means of 1H, 13C NMR and IR spectroscopy, mass spectrometry and elemental analysis.
Yuliya Ryzhkova; Artem Fakhrutdinov; Michail Elinson. Ammonium Salts of 5-(3-Chromenyl)-5H-chromeno[2,3-b]pyridines. Molbank 2021, 2021, M1219 .
AMA StyleYuliya Ryzhkova, Artem Fakhrutdinov, Michail Elinson. Ammonium Salts of 5-(3-Chromenyl)-5H-chromeno[2,3-b]pyridines. Molbank. 2021; 2021 (2):M1219.
Chicago/Turabian StyleYuliya Ryzhkova; Artem Fakhrutdinov; Michail Elinson. 2021. "Ammonium Salts of 5-(3-Chromenyl)-5H-chromeno[2,3-b]pyridines." Molbank 2021, no. 2: M1219.
A continuously growing interest in convenient and ‘green’ reaction techniques encourages organic chemists to elaborate on new synthetic methodologies. Nowadays, organic electrochemistry is a new useful method with important synthetic and ecological advantages. The employment of an electrocatalytic methodology in cascade reactions is very promising because it provides the combination of the synthetic virtues of the cascade strategy with the ecological benefits and convenience of electrocatalytic procedures. In this research, a new type of the electrocatalytic cascade transformation was found: the electrochemical cyclization of 1,3-dimethyl-5-[[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl](aryl)methyl]pyrimidine-2,4,6(1H,3H,5H)-triones was carried out in alcohols in an undivided cell in the presence of sodium halides with the selective formation of spiro[furo[3,2-b]pyran-2,5′-pyrimidines] in 59-95% yields. This new electrocatalytic process is a selective, facile, and efficient way to create spiro[furo[3,2-b]pyran-2,5′-pyrimidines], which are pharmacologically active heterocyclic systems with different biomedical applications. Spiro[furo[3,2-b]pyran-2,5′-pyrimidines] were found to occupy the binding pocket of aldose reductase and inhibit it. The values of the binding energy and Lead Finder’s Virtual Screening scoring function showed that the formation of protein–ligand complexes was favorable. The synthesized compounds are promising for the inhibition of aldose reductase. This makes them interesting for study in the treatment of diabetes or similar diseases.
Michail Elinson; Anatoly Vereshchagin; Yuliya Ryzhkova; Fedor Ryzhkov; Artem Fakhrutdinov; Mikhail Egorov. Efficient Electrocatalytic Approach to Spiro[Furo[3,2-b]pyran-2,5′-pyrimidine] Scaffold as Inhibitor of Aldose Reductase. Electrochem 2021, 2, 295 -310.
AMA StyleMichail Elinson, Anatoly Vereshchagin, Yuliya Ryzhkova, Fedor Ryzhkov, Artem Fakhrutdinov, Mikhail Egorov. Efficient Electrocatalytic Approach to Spiro[Furo[3,2-b]pyran-2,5′-pyrimidine] Scaffold as Inhibitor of Aldose Reductase. Electrochem. 2021; 2 (2):295-310.
Chicago/Turabian StyleMichail Elinson; Anatoly Vereshchagin; Yuliya Ryzhkova; Fedor Ryzhkov; Artem Fakhrutdinov; Mikhail Egorov. 2021. "Efficient Electrocatalytic Approach to Spiro[Furo[3,2-b]pyran-2,5′-pyrimidine] Scaffold as Inhibitor of Aldose Reductase." Electrochem 2, no. 2: 295-310.
Michail N. Elinson; Yuliya E. Ryzhkova; Fedor V. Ryzhkov. Multicomponent design of chromeno[2,3-b]pyridine systems. Russian Chemical Reviews 2021, 90, 94 -115.
AMA StyleMichail N. Elinson, Yuliya E. Ryzhkova, Fedor V. Ryzhkov. Multicomponent design of chromeno[2,3-b]pyridine systems. Russian Chemical Reviews. 2021; 90 (1):94-115.
Chicago/Turabian StyleMichail N. Elinson; Yuliya E. Ryzhkova; Fedor V. Ryzhkov. 2021. "Multicomponent design of chromeno[2,3-b]pyridine systems." Russian Chemical Reviews 90, no. 1: 94-115.
The Pot, Atom, and Step Economy (PASE) approach is based on the Pot economy principle and unites it with the Atom and Step Economy strategies; it ensures high efficiency, simplicity and low waste formation. The PASE approach is widely used in multicomponent chemistry. This approach was adopted for the synthesis of previously unknown hydroxyquinolinone substituted chromeno[2,3-b]pyridines via reaction of salicylaldehydes, malononitrile dimer and hydroxyquinolinone. It was shown that an ethanol-pyridine combination is more beneficial than other inorganic or organic catalysts. Quantum chemical studies showed that chromeno[2,3-b]pyridines has potential for corrosion inhibition. Real time 1H NMR monitoring was used for the investigation of reaction mechanism and 2-((2H-chromen-3-yl)methylene)malononitrile was defined as a key intermediate in the reaction.
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 2020, 25, 2573 .
AMA StyleFedor 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. 2020; 25 (11):2573.
Chicago/Turabian StyleFedor V. Ryzhkov; Yuliya E. Ryzhkova; Michail N. Elinson; Stepan V. Vorobyev; Artem N. Fakhrutdinov; Anatoly N. Vereshchagin; Mikhail P. Egorov. 2020. "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, no. 11: 2573.
In this communication, the electrochemically induced multicomponent transformation of 3-methylbenzaldehyde, 3-(4-bromophenyl)isoxazol-5(4H)-one and kojic acid in n-PrOH in an undivided cell in the presence of sodium bromide was carefully investigated to give 3-(4-bromophenyl)-4-{[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl](m-tolyl)methyl}isoxa- zol-5(2H)-one in good yield. The structure of the new compound was established by means of elemental analysis, mass-, nuclear magnetic resonance and infrared spectroscopy. Furthermore, its structure was determined and confirmed by X-ray analysis. The synthesized compound is a promising compound for different biomedical applications, and, in particular, for the regulation of inflammatory diseases, as shown by docking studies in this research.
Yuliya E. Ryzhkova; Fedor V. Ryzhkov; Michail N. Elinson. 3-(4-Bromophenyl)-4-{[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl](m-tolyl)methyl}isoxazol-5(2H)-one. Molbank 2020, 2020, M1135 .
AMA StyleYuliya E. Ryzhkova, Fedor V. Ryzhkov, Michail N. Elinson. 3-(4-Bromophenyl)-4-{[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl](m-tolyl)methyl}isoxazol-5(2H)-one. Molbank. 2020; 2020 (2):M1135.
Chicago/Turabian StyleYuliya E. Ryzhkova; Fedor V. Ryzhkov; Michail N. Elinson. 2020. "3-(4-Bromophenyl)-4-{[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl](m-tolyl)methyl}isoxazol-5(2H)-one." Molbank 2020, no. 2: M1135.