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Electrocatalytic cascade assembly of benzylidenebarbiturates and cyclohexane-1,3-diones in methanol in the presence of sodium bromide as mediator in an undivided cell results in the formation of dihydro-2'H,3H-spiro[1-benzofuran-2,5'-pyrimidines] in 72–85% yields. This electrochemical process occurs under mild conditions, and the isolation procedure after the reaction is simple. The structures of the final compounds were confirmed by 1H–13C HMBC spectroscopy.
Fedor V. Ryzhkov; Michail N. Elinson; Yuliya E. Ryzhkova; Anatoly N. Vereshchagin; Artem N. Fakhrutdinov; Mikhail P. Egorov. Electrocatalytic cascade approach to the synthesis of dihydro-2'H,3H-spiro[1-benzofuran-2,5'-pyrimidines]. Chemistry of Heterocyclic Compounds 2021, 57, 672 -678.
AMA StyleFedor V. Ryzhkov, Michail N. Elinson, Yuliya E. Ryzhkova, Anatoly N. Vereshchagin, Artem N. Fakhrutdinov, Mikhail P. Egorov. Electrocatalytic cascade approach to the synthesis of dihydro-2'H,3H-spiro[1-benzofuran-2,5'-pyrimidines]. Chemistry of Heterocyclic Compounds. 2021; 57 (6):672-678.
Chicago/Turabian StyleFedor V. Ryzhkov; Michail N. Elinson; Yuliya E. Ryzhkova; Anatoly N. Vereshchagin; Artem N. Fakhrutdinov; Mikhail P. Egorov. 2021. "Electrocatalytic cascade approach to the synthesis of dihydro-2'H,3H-spiro[1-benzofuran-2,5'-pyrimidines]." Chemistry of Heterocyclic Compounds 57, no. 6: 672-678.
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.
The new electrocatalytic multicomponent transformation has been found: the electrolysis of arylaldehydes, N,N′‐dimethylbarbiturate, and cycloxehane‐1,3‐diones in alcohols in the presence of sodium bromide as a mediator in an undivided cell results in the formation of substituted unsymmetric spirobarbituric dihydrofurans in 62%–76% yields. The optimized reaction conditions and a mechanistic rationale for this electrocatalytic multicomponent transformation are presented. This new electrocatalytic process is a facile and efficient way to produce substituted unsymmetric spirobarbituric dihydrofurans containing both barbituric and 3,5,6,7‐tetrahydro‐1‐benzofuran‐4(2H)‐one fragments, which are promising compounds for different biomedical applications, among them are anticonvulsants, anti‐AIDS agents, and antiinflammatory remedies. The scaffold approach was employed to find a protein, which may be influenced by the synthesized compounds—human aldose reductase was proposed. It was shown by molecular docking studies that such a scaffold search is beneficial and tetrahydro‐2′H,4H‐spiro[benzofuran‐2,5′‐pyrimidines] used in this approach are promising for the development of novel aldose reductase inhibitors.
Michail N. Elinson; Yuliya E. Ryzhkova; Anatoly N. Vereshchagin; Fedor V. Ryzhkov; Mikhail P. Egorov. Electrocatalytic multicomponent one‐pot approach to tetrahydro‐2′ H , 4 H ‐spiro[benzofuran‐2,5′‐pyrimidine] scaffold. Journal of Heterocyclic Chemistry 2021, 58, 1484 -1495.
AMA StyleMichail N. Elinson, Yuliya E. Ryzhkova, Anatoly N. Vereshchagin, Fedor V. Ryzhkov, Mikhail P. Egorov. Electrocatalytic multicomponent one‐pot approach to tetrahydro‐2′ H , 4 H ‐spiro[benzofuran‐2,5′‐pyrimidine] scaffold. Journal of Heterocyclic Chemistry. 2021; 58 (7):1484-1495.
Chicago/Turabian StyleMichail N. Elinson; Yuliya E. Ryzhkova; Anatoly N. Vereshchagin; Fedor V. Ryzhkov; Mikhail P. Egorov. 2021. "Electrocatalytic multicomponent one‐pot approach to tetrahydro‐2′ H , 4 H ‐spiro[benzofuran‐2,5′‐pyrimidine] scaffold." Journal of Heterocyclic Chemistry 58, no. 7: 1484-1495.
Electrocatalytic transformation of aldehydes with two equivalents of 1,3-diethyl-2-thiobarbituric acid has been carried out in alcohols in an undivided cell in the presence of sodium halides with the selective formation of the substituted 5,5'-(arylmethylene)bis(1,3-diethyl-2-thiobarbituric acids) in 87–98% yields and with 870–980% current efficiency. This new one-pot electrochemically induced tandem Knoevenagel–Michael process is a simple and efficient approach to substituted 5,5'-(arylmethylene)bis(1,3-diethyl-2-thiobarbituric acids) containing two 1,3-diethyl-2-thiobarbituric acid fragments separated by C-aryl-substituted spacer, which are promising compounds for different biomedical applications, including anticonvulsant, antiAIDS agents and anti-inflammatory remedies. Theoretical studies were carried out to investigate the interaction of the synthesized compounds with beef and human catalases.
Michail N. Elinson; Anatoly N. Vereshchagin; Yuliya E. Ryzhkova; Kirill A. Karpenko; Fedor V. Ryzhkov; Mikhail P. Egorov. Electrocatalytic tandem assembly of aldehydes with 2-thiobarbituric acid into 5,5'-(arylmethylene)bis(1,3-diethyl-2-thiobarbituric acids) and evaluation of their interaction with catalases. Chemistry of Heterocyclic Compounds 2021, 57, 274 -283.
AMA StyleMichail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Ryzhkova, Kirill A. Karpenko, Fedor V. Ryzhkov, Mikhail P. Egorov. Electrocatalytic tandem assembly of aldehydes with 2-thiobarbituric acid into 5,5'-(arylmethylene)bis(1,3-diethyl-2-thiobarbituric acids) and evaluation of their interaction with catalases. Chemistry of Heterocyclic Compounds. 2021; 57 (3):274-283.
Chicago/Turabian StyleMichail N. Elinson; Anatoly N. Vereshchagin; Yuliya E. Ryzhkova; Kirill A. Karpenko; Fedor V. Ryzhkov; Mikhail P. Egorov. 2021. "Electrocatalytic tandem assembly of aldehydes with 2-thiobarbituric acid into 5,5'-(arylmethylene)bis(1,3-diethyl-2-thiobarbituric acids) and evaluation of their interaction with catalases." Chemistry of Heterocyclic Compounds 57, no. 3: 274-283.
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.
Multicomponent reactions (MCRs) are important processes, in which more than three different reactants directly get converted into one new structure bearing most of the atoms of these reactants. It is a very powerful tool in drug discovery and combinational chemistry. A new pseudo‐four‐component synthetic approach to 5‐(5‐hydroxy‐3‐methyl‐1H‐pyrazol‐4‐yl)‐substituted 5H‐chromeno[2,3‐b]pyridines with 68%–95% yields is reported. This MCR opens an efficient and convenient way to substituted 5H‐chromeno[2,3‐b]pyridines, which are promising compounds in medicinal chemistry and for the treatment of lung cancer through inhibition of aldo‐keto reductase 1B10. A new consensus approach of molecular docking and molecular dynamics was applied for the investigation of interaction of synthesized 5H‐chromeno[2,3‐b]pyridines and aldo‐keto reductase 1B10.
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‐1 H ‐pyrazol‐4‐yl)‐substituted 5 H ‐chromeno[2,3‐ b ]pyridines. Journal of Heterocyclic Chemistry 2020, 58, 793 -804.
AMA StyleFedor 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‐1 H ‐pyrazol‐4‐yl)‐substituted 5 H ‐chromeno[2,3‐ b ]pyridines. Journal of Heterocyclic Chemistry. 2020; 58 (3):793-804.
Chicago/Turabian StyleFedor V. Ryzhkov; Michail N. Elinson; Yuliya E. Ryzhkova; Anatoly N. Vereshchagin; Victor A. Korolev; Mikhail P. Egorov. 2020. "Pseudo‐four‐component synthesis and in silico studies of 5‐( 5‐hydroxy‐3‐methyl‐1 H ‐pyrazol‐4‐yl)‐substituted 5 H ‐chromeno[2,3‐ b ]pyridines." Journal of Heterocyclic Chemistry 58, no. 3: 793-804.
Multicomponent reactions employ three or more reactants to obtain heterocycles containing fragments of all starting materials in a onepot process. All new bonds are formed at once, hence multicomponent reactions are characterized by high bond-forming index. A new multicomponent, one-pot reaction yielding previously unknown 5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-5H-chromeno[2,3-b]pyridines in 52–94% yield has been found. This multicomponent approach allows to construct four new bonds to synthesize some 5H-chromeno[2,3-b]-pyridines under mild conditions. Molecular docking and dynamics studies of the synthesized structures were carried out to identify their interaction with the binding pocket of the neuropeptide Y1 receptor.
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. Chemistry of Heterocyclic Compounds 2020, 56, 1560 -1568.
AMA StyleFedor 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. Chemistry of Heterocyclic Compounds. 2020; 56 (12):1560-1568.
Chicago/Turabian StyleFedor V. Ryzhkov; Yuliya E. Ryzhkova; Michail N. Elinson; Anatoly N. Vereshchagin; Victor A. Korolev; Mikhail P. Egorov. 2020. "Quadruple Bond Forming Multicomponent Approach to 5-(3-chromenyl)-5H-chromeno[2,3-b]pyridines and Its Interaction with the Neuropeptide Y1 Receptor." Chemistry of Heterocyclic Compounds 56, no. 12: 1560-1568.
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.
The new electrochemically induced multicomponent assembling has been accomplished: the electrocatalytic transformation of aldehydes, 3‐aryl‐substituted isoxazol‐5(4H )‐ones and kojic acid has been carried out in alcohols in an undivided cell in the presence of sodium halides. This transformation proceeds with the selective formation of the earlier unknown substituted 4‐{[3‐hydroxy‐6‐(hydroxymethyl)‐4‐oxo‐4H ‐pyran‐2‐yl]‐(aryl)methyl}‐isoxazol‐5(2H )‐ones in 57–93 % yields with 190–310 % current efficiency. This new electrocatalytic process provides a facile and efficient way to the separated by C‐aryl‐substituted spacer 3‐arylisoxazol‐5(4H )‐one and kojic acid pharmacology active heterocyclic fragments, which are promising compounds for different biomedical applications, and, in particular, for regulation of inflammatory as was shown by docking studies in this research.
Michail N. Elinson; Yuliya E. Ryzhkova; Fedor Ryzhkov; Anatoly N. Vereshchagin; Natalia A. Leonova; Mikhail P. Egorov. Electrochemically Induced Facile and Efficient Multicomponent Approach to Medicinally Relevant 4‐[4‐oxo‐4 H ‐pyran‐2‐yl](aryl)‐methylisoxazol‐5(2 H )‐one Scaffold. ChemistrySelect 2020, 5, 5981 -5986.
AMA StyleMichail N. Elinson, Yuliya E. Ryzhkova, Fedor Ryzhkov, Anatoly N. Vereshchagin, Natalia A. Leonova, Mikhail P. Egorov. Electrochemically Induced Facile and Efficient Multicomponent Approach to Medicinally Relevant 4‐[4‐oxo‐4 H ‐pyran‐2‐yl](aryl)‐methylisoxazol‐5(2 H )‐one Scaffold. ChemistrySelect. 2020; 5 (20):5981-5986.
Chicago/Turabian StyleMichail N. Elinson; Yuliya E. Ryzhkova; Fedor Ryzhkov; Anatoly N. Vereshchagin; Natalia A. Leonova; Mikhail P. Egorov. 2020. "Electrochemically Induced Facile and Efficient Multicomponent Approach to Medicinally Relevant 4‐[4‐oxo‐4 H ‐pyran‐2‐yl](aryl)‐methylisoxazol‐5(2 H )‐one Scaffold." ChemistrySelect 5, no. 20: 5981-5986.
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.
Michail N. Elinson; Anatoly N. Vereshchagin; Fedor Ryzhkov; Yuliya E. Anisina. ‘Solvent-free’ and ‘on-solvent’ multicomponent reaction of isatins, malononitrile, and bicyclic CH-acids: fast and efficient way to medicinal privileged spirooxindole scaffold. Arkivoc 2018, 2018, 276 -285.
AMA StyleMichail N. Elinson, Anatoly N. Vereshchagin, Fedor Ryzhkov, Yuliya E. Anisina. ‘Solvent-free’ and ‘on-solvent’ multicomponent reaction of isatins, malononitrile, and bicyclic CH-acids: fast and efficient way to medicinal privileged spirooxindole scaffold. Arkivoc. 2018; 2018 (4):276-285.
Chicago/Turabian StyleMichail N. Elinson; Anatoly N. Vereshchagin; Fedor Ryzhkov; Yuliya E. Anisina. 2018. "‘Solvent-free’ and ‘on-solvent’ multicomponent reaction of isatins, malononitrile, and bicyclic CH-acids: fast and efficient way to medicinal privileged spirooxindole scaffold." Arkivoc 2018, no. 4: 276-285.
The new type of ‘on-solvent’ multicomponent reaction was found: transformation of benzaldehydes, malononitrile and 4–hydroxy-6-methylpyridin-2(1H)-one in the presence of sodium acetate as catalyst in a small amount of ethanol results in formation of substituted 2-amino-7-methyl-5-oxo-4-phenyl-5,6-dihydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles in excellent 92–99% yields. This novel ‘one-pot’ process opens an efficient and convenient way to functionalize pyrano[3,2-c]pyridine systems, which are promising compounds for different biomedical applications.
Michail N. Elinson; Fedor V. Ryzhkov; Anatoly N. Vereshchagin; Alexander S. Goloveshkin; Ivan S. Bushmarinov; Mikhail P. Egorov. Efficient and facile ‘on-solvent’ multicomponent synthesis of medicinally privileged pyrano[3,2-c]pyridine scaffold. Research on Chemical Intermediates 2018, 44, 3199 -3209.
AMA StyleMichail N. Elinson, Fedor V. Ryzhkov, Anatoly N. Vereshchagin, Alexander S. Goloveshkin, Ivan S. Bushmarinov, Mikhail P. Egorov. Efficient and facile ‘on-solvent’ multicomponent synthesis of medicinally privileged pyrano[3,2-c]pyridine scaffold. Research on Chemical Intermediates. 2018; 44 (5):3199-3209.
Chicago/Turabian StyleMichail N. Elinson; Fedor V. Ryzhkov; Anatoly N. Vereshchagin; Alexander S. Goloveshkin; Ivan S. Bushmarinov; Mikhail P. Egorov. 2018. "Efficient and facile ‘on-solvent’ multicomponent synthesis of medicinally privileged pyrano[3,2-c]pyridine scaffold." Research on Chemical Intermediates 44, no. 5: 3199-3209.
Michail N. Elinson; Fedor V. Ryzhkov; Anatoly N. Vereshchagin; Alexander D. Korshunov; Roman A. Novikov; Mikhail P. Egorov. ‘On-solvent’ new domino reaction of salicylaldehyde, malononitrile and 4-hydroxy-6-methylpyridin-2(1 H )-one: fast and efficient approach to medicinally relevant 4-pyridinyl-2-amino-4 H -chromene scaffold. Mendeleev Communications 2017, 27, 559 -561.
AMA StyleMichail N. Elinson, Fedor V. Ryzhkov, Anatoly N. Vereshchagin, Alexander D. Korshunov, Roman A. Novikov, Mikhail P. Egorov. ‘On-solvent’ new domino reaction of salicylaldehyde, malononitrile and 4-hydroxy-6-methylpyridin-2(1 H )-one: fast and efficient approach to medicinally relevant 4-pyridinyl-2-amino-4 H -chromene scaffold. Mendeleev Communications. 2017; 27 (6):559-561.
Chicago/Turabian StyleMichail N. Elinson; Fedor V. Ryzhkov; Anatoly N. Vereshchagin; Alexander D. Korshunov; Roman A. Novikov; Mikhail P. Egorov. 2017. "‘On-solvent’ new domino reaction of salicylaldehyde, malononitrile and 4-hydroxy-6-methylpyridin-2(1 H )-one: fast and efficient approach to medicinally relevant 4-pyridinyl-2-amino-4 H -chromene scaffold." Mendeleev Communications 27, no. 6: 559-561.
Anatoly N. Vereshchagin; Michail Elinson; Yuliya E. Anisina; Fedor Ryzhkov; Alexander S. Goloveshkin; Roman A. Novikov; Mikhail P. Egorov. Synthesis, structural, spectroscopic and docking studies of new 5C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles. Journal of Molecular Structure 2017, 1146, 766 -772.
AMA StyleAnatoly N. Vereshchagin, Michail Elinson, Yuliya E. Anisina, Fedor Ryzhkov, Alexander S. Goloveshkin, Roman A. Novikov, Mikhail P. Egorov. Synthesis, structural, spectroscopic and docking studies of new 5C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles. Journal of Molecular Structure. 2017; 1146 ():766-772.
Chicago/Turabian StyleAnatoly N. Vereshchagin; Michail Elinson; Yuliya E. Anisina; Fedor Ryzhkov; Alexander S. Goloveshkin; Roman A. Novikov; Mikhail P. Egorov. 2017. "Synthesis, structural, spectroscopic and docking studies of new 5C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles." Journal of Molecular Structure 1146, no. : 766-772.
A pot, atom and step economy (PASE) synthesis of new 5-C substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles was carried out. This process involves the one-pot, pseudo four-component reaction of salicylaldehydes, malononitrile, 1,3-cyclohexanediones and Et3N as a catalyst in acetonitrile at reflux. This novel one-pot reaction provides an effective and convenient way to 5-C cyclohexyl-functionalized chromeno[2,3-b]pyridines, which are promising compounds for different biomedical applications. The procedure utilizes readily available reagents, it is easily carried out and the work up is not complicated. 2,4-diamino-5-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitriles are crystallized directly from the reaction mixture and the isolation includes only filtration. Molecular docking studies of the synthesized 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles were also carried out to elucidate their relationship with the binding pockets of the mitogen activated protein kinase (MK).
Anatoly N. Vereshchagin; Michail N. Elinson; Yuliya E. Anisina; Fedor V. Ryzhkov; Roman A. Novikov; Mikhail P. Egorov. PASE Pseudo-Four-Component Synthesis and Docking Studies of New 5-C-Substituted 2,4-Diamino-5H-Chromeno[2,3-b]pyridine-3-Carbonitriles. ChemistrySelect 2017, 2, 4593 -4597.
AMA StyleAnatoly N. Vereshchagin, Michail N. Elinson, Yuliya E. Anisina, Fedor V. Ryzhkov, Roman A. Novikov, Mikhail P. Egorov. PASE Pseudo-Four-Component Synthesis and Docking Studies of New 5-C-Substituted 2,4-Diamino-5H-Chromeno[2,3-b]pyridine-3-Carbonitriles. ChemistrySelect. 2017; 2 (17):4593-4597.
Chicago/Turabian StyleAnatoly N. Vereshchagin; Michail N. Elinson; Yuliya E. Anisina; Fedor V. Ryzhkov; Roman A. Novikov; Mikhail P. Egorov. 2017. "PASE Pseudo-Four-Component Synthesis and Docking Studies of New 5-C-Substituted 2,4-Diamino-5H-Chromeno[2,3-b]pyridine-3-Carbonitriles." ChemistrySelect 2, no. 17: 4593-4597.
A new stereoselective cascade reaction of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid by the action of bromine in the presence of a base into substituted (barbituric acid)-5-spirocyclopropanes is described. The yields are in the range of 60%–75%. Nuclear magnetic resonance (NMR) studies indicate that this cascade transformation results in the stereoselective formation of spiro products with trans-configuration of aryl and alkoxycarbonyl substituents in the cyclopropane ring. The products are a perspective class of compounds with prominent pharmacological and physiological activity.
Michail N. Elinson; Anatoly N. Vereshchagin; Alexander D. Korshunov; Fedor V. Ryzhkov; Mikhail P. Egorov. Stereoselective cascade assembling of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid into (1R*,2S*)-1-cyano-5,7-dialkyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro[2.5]octane-1-carboxylates. Heterocyclic Communications 2017, 23, 85 -90.
AMA StyleMichail N. Elinson, Anatoly N. Vereshchagin, Alexander D. Korshunov, Fedor V. Ryzhkov, Mikhail P. Egorov. Stereoselective cascade assembling of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid into (1R*,2S*)-1-cyano-5,7-dialkyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro[2.5]octane-1-carboxylates. Heterocyclic Communications. 2017; 23 (2):85-90.
Chicago/Turabian StyleMichail N. Elinson; Anatoly N. Vereshchagin; Alexander D. Korshunov; Fedor V. Ryzhkov; Mikhail P. Egorov. 2017. "Stereoselective cascade assembling of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid into (1R*,2S*)-1-cyano-5,7-dialkyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro[2.5]octane-1-carboxylates." Heterocyclic Communications 23, no. 2: 85-90.
The general ‘on-solvent’ PASE approach was found to be medicinally relevant for 4H,5H-pyrano[4,3-b]pyran-5-one and 4,6-dihydro-5H-pyrano[3,2-c]pyridine-5-one scaffolds. Ammonium acetate-catalyzed multicomponent reaction of aldehydes and two different C–H acids in the presence of small amounts of EtOH results in fast (3 – 15 min) and efficient formation of scaffolds, promising for many diverse oriented medical applications.
Michail N. Elinson; Fedor V. Ryzhkov; Ruslan F. Nasybullin; Anatoly N. Vereshchagin; Mikhail P. Egorov. Fast Efficient and General PASE Approach to Medicinally Relevant 4H,5H-Pyrano-[4,3-b]pyran-5-one and 4,6-Dihydro-5H-pyrano-[3,2-c]pyridine-5-one Scaffolds. Helvetica Chimica Acta 2016, 99, 724 -731.
AMA StyleMichail N. Elinson, Fedor V. Ryzhkov, Ruslan F. Nasybullin, Anatoly N. Vereshchagin, Mikhail P. Egorov. Fast Efficient and General PASE Approach to Medicinally Relevant 4H,5H-Pyrano-[4,3-b]pyran-5-one and 4,6-Dihydro-5H-pyrano-[3,2-c]pyridine-5-one Scaffolds. Helvetica Chimica Acta. 2016; 99 (9):724-731.
Chicago/Turabian StyleMichail N. Elinson; Fedor V. Ryzhkov; Ruslan F. Nasybullin; Anatoly N. Vereshchagin; Mikhail P. Egorov. 2016. "Fast Efficient and General PASE Approach to Medicinally Relevant 4H,5H-Pyrano-[4,3-b]pyran-5-one and 4,6-Dihydro-5H-pyrano-[3,2-c]pyridine-5-one Scaffolds." Helvetica Chimica Acta 99, no. 9: 724-731.
Michail N. Elinson; Fedor V. Ryzhkov; Anatoly N. Vereshchagin; Tatiana A. Zaimovskaya; Victor A. Korolev; Mikhail P. Egorov. Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4’-pyrano[3,2-c]pyridine]-2,5’(6’H)-dione scaffold. Mendeleev Communications 2016, 26, 399 -401.
AMA StyleMichail N. Elinson, Fedor V. Ryzhkov, Anatoly N. Vereshchagin, Tatiana A. Zaimovskaya, Victor A. Korolev, Mikhail P. Egorov. Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4’-pyrano[3,2-c]pyridine]-2,5’(6’H)-dione scaffold. Mendeleev Communications. 2016; 26 (5):399-401.
Chicago/Turabian StyleMichail N. Elinson; Fedor V. Ryzhkov; Anatoly N. Vereshchagin; Tatiana A. Zaimovskaya; Victor A. Korolev; Mikhail P. Egorov. 2016. "Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4’-pyrano[3,2-c]pyridine]-2,5’(6’H)-dione scaffold." Mendeleev Communications 26, no. 5: 399-401.
This review is concerned with modern trends in the use of electrochemically induced chain reactions in cascade and multicomponent electroorganic synthesis. The review summarizes the data on the use of electrochemically induced chain reactions in cascade and multicomponent organic synthesis, which were published mainly in the last decade.
Michail N. Elinson; Anatoly N. Vereshchagin; Fedor V. Ryzhkov. Catalysis of Cascade and Multicomponent Reactions of Carbonyl Compounds and C-H Acids by Electricity. The Chemical Record 2016, 16, 1950 -1964.
AMA StyleMichail N. Elinson, Anatoly N. Vereshchagin, Fedor V. Ryzhkov. Catalysis of Cascade and Multicomponent Reactions of Carbonyl Compounds and C-H Acids by Electricity. The Chemical Record. 2016; 16 (4):1950-1964.
Chicago/Turabian StyleMichail N. Elinson; Anatoly N. Vereshchagin; Fedor V. Ryzhkov. 2016. "Catalysis of Cascade and Multicomponent Reactions of Carbonyl Compounds and C-H Acids by Electricity." The Chemical Record 16, no. 4: 1950-1964.
Fast (3 min) pot, atom and step economics (PASE) potassium fluoride catalyzed multicomponent reaction of isatins, malononitrile and 4-hydroxy-6-methyl-2H-pyran-2-one results in efficient formation of substituted spirooxindole-3,4′-pyrano[4,3-b]pyrans in 92–96% yields. The developed ‘on-solvent’ approach to the substituted spirooxindole-3,4′-pyrano[4,3-b]pyrans – the pharmacologically perspective substances with known antiviral, antileishmanial, anticonvulsant and anti-HIV activities – is beneficial from the viewpoint of diversity-oriented large-scale processes and represents fast and environmentally benign synthetic concept for the multicomponent reactions strategy.
Michail N. Elinson; Fedor Ryzhkov; Victor A. Korolev; Mikhail P. Egorov. Pot, atom and step-economic (PASE) synthesis of medicinally relevant spiro[oxindole-3,4′-pyrano[4,3-b]pyran] scaffold. Heterocyclic Communications 2016, 22, 11 -15.
AMA StyleMichail N. Elinson, Fedor Ryzhkov, Victor A. Korolev, Mikhail P. Egorov. Pot, atom and step-economic (PASE) synthesis of medicinally relevant spiro[oxindole-3,4′-pyrano[4,3-b]pyran] scaffold. Heterocyclic Communications. 2016; 22 (1):11-15.
Chicago/Turabian StyleMichail N. Elinson; Fedor Ryzhkov; Victor A. Korolev; Mikhail P. Egorov. 2016. "Pot, atom and step-economic (PASE) synthesis of medicinally relevant spiro[oxindole-3,4′-pyrano[4,3-b]pyran] scaffold." Heterocyclic Communications 22, no. 1: 11-15.