S. V. Karpov
Chuvash State University
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Featured researches published by S. V. Karpov.
Russian Journal of Organic Chemistry | 2011
S. V. Karpov; Ya. S. Kayukov; I. N. Bardasov; O. V. Ershov; O. E. Nasakin; O. V. Kayukova
Reactions of 2-aroyl-1,1,3,3-tetracyanopropenides with thiols in acid medium led to the formation of the corresponding 2-alkylsulfanyl-substituted 2-(5-amino-2-aryl-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles.
Russian Journal of Organic Chemistry | 2011
S. V. Karpov; Ya. S. Kayukov; I. N. Bardasov; O. V. Kayukova; O. V. Ershov; O. E. Nasakin
Potassium 2-aroyl-1,1,3,3-tetracyanopropenides reacted with concentrated hydrochloric acid to give the corresponding 2-[5-amino-2-aryl-2-chloro-4-cyanofuran-3(2H)-ylidene]propanedinitriles.
Russian Journal of Organic Chemistry | 2012
Ya. S. Kayukov; I. N. Bardasov; S. V. Karpov; O. V. Ershov; O. E. Nasakin; O. V. Kayukova; V. A. Tafeenko
Reaction of 2,2,3,3-tetracyanocyclopropyl ketones with water solution of sodium hydroxide after neutralization with sulfuric acid leads to the formation of 4-amino-1-hydroxy-3,6-dioxo-2,3,5,6-tetrahydro-1Hpyrrolo[3,4-c]pyridine-7-carbonitriles. Pivaloyltetracyanocyclopropane reacts in another way and is converted into sodium 6a-tert-butyl-3,4-dicyano-5-oxo-1,5,6,6a-tetrahydropyrrolo[2,3-b]pyrrol-2-olate. 1-Benzoyl-1-methylcyclopropane-2,2,3,3-tetracarbonitrile reacts with the sodium hydroxide with the retention of the threemembered ring and the formation of 11-methyl-4-phenyl-3,5,9-triazatetracyclo[5.3.1.01,7.04,11]undecane-2,6,8,10-tetraone.
Journal of Organic Chemistry | 2016
S. V. Karpov; Arthur A. Grigor’ev; Yakov S. Kayukov; Irina V. Karpova; O. E. Nasakin; V. A. Tafeenko
A novel route for synthesis of 2-acyl-1,1,3,3-tetracyanopropenides (ATCN) salts in high yields and excellent purities starting from readily available methyl ketones, malononitrile, bromine, and alkali metal acetates is reported. The starting aryl(heteroaryl) methyl ketones were oxidized to the corresponding α-ketoaldehydes by new a DMSO-NaBr-H2SO4 oxidation system in yields up to 90% within a short reaction time of 8-10 min. The subsequent stages of ATCN preparation are realized in aqueous media without use of any toxic solvents, in accordance with principle 5 of green chemistry. Lithium, sodium, potassium, rubidium, and cesium 2-benzoyl-1,1,3,3-tetracyanopropenides were characterized by X-ray diffraction analysis. These salts show a good potential for synthesis of five- and six-membered heterocycles and may serve as potentially useful ligands in coordination and supramolecular chemistry.
Chemistry of Heterocyclic Compounds | 2017
Arthur A. Grigor’ev; S. V. Karpov; Yakov S. Kayukov; O. E. Nasakin; Iuliia A. Gracheva; V. A. Tafeenko
n 2-Acyl-1,1,3,3-tetracyanopropenides undergo cascade heterocyclization under the action of mercaptoacetic esters, leading to the formation of new 3,6-diamino-4-aroyl-5-cyanothieno[2,3-b]pyridine-2-carboxylates. The fast and convenient synthetic way to highly substituted thieno[2,3-b]pyridine scaffold is described.
Russian Journal of Organic Chemistry | 2013
Ya. S. Kayukov; S. V. Karpov; M. M. Rizatdinov; I. N. Bardasov; O. V. Ershov; O. E. Nasakin; V. A. Tafeenko
Reactions of 2-acyl(aroyl)-1,1,3,3-tetracyanopropenides with hydrazine hydrate followed by neutralization led to the formation of 2-amino-4-[hydrazono(aryl)methyl]-2-oxo-1,2-dihydropyridine-3,5-dicarbonitriles.
Russian Journal of Organic Chemistry | 2012
Ya. S. Kayukov; S. V. Karpov; I. N. Bardasov; O. V. Kayukova; O. V. Ershov; O. E. Nasakin
The reaction of sodium 2-acyl(aroyl)-1,1,3,3-tetracyanopropenides with hydroiodic acid at heating led to the formation of 1-alkyl(aryl)-4-amino-6-iodo-3-oxo-1,3-dihydrofuro[3,4-c]pyridine-7-carbonitriles.
Russian Journal of Organic Chemistry | 2011
S. V. Karpov; Ya. S. Kayukov; I. N. Bardasov; O. V. Kayukova; K. V. Lipin; O. E. Nasakin
Abstract2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides reacted with hydrogen halides along two concurrent pathways with formation of furan or pyridine derivatives. The reaction in butan-2-ol afforded 2-amino-4-acyl-(aroyl)-6-halopyridine-3,5-dicarbonitriles, whereas the major products in the reactions with HCl and HBr in aqueous solution were the corresponding 2-(5-amino-2-aryl-2-chloro(bromo)-4-cyano-2,3-dihydrofuran-3-ylidene)malononitriles. The reaction with aqueous hydrogen iodide was accompanied by reductive deiodination and produced 2-(5-amino-2-aryl-4-cyano-2,3-dihydrofuran-3-ylidene)malononitriles.
Russian Journal of Organic Chemistry | 2014
Ya. S. Kayukov; S. V. Karpov; O. V. Kayukova; O. V. Ershov; O. E. Nasakin
Reactions of 2-aroyl-1,1,3,3-tetracyanopropenides with hydrogen halides in solvents of low dielectric permittivity result in the formation of 6-amino-2-aroyl-2-halopyridine-3,5-dicarbonitriles. 2-Acyl-1,1,3,3-tetracyanopropenides under similar conditions afford 2-(2-alkylidene-5-amino-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles. In solvents of high dielectric permittivity the result of the reaction depends on the nature of the hydrogen halide and the acyl(aroyl) substituent: With HCl and HBr 2-aroyl-1,1,3,3-tetracyanopropenides form 2-(5-amino-2-aryl-2-halo-4-cyano-2,3-dihydrofuran-3-ylidene)-propanedinitriles, and 2-acyl-1,1,3,3-tetracyanopropenides give 2-(2-alkylidene-5-amino-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles; with HI depending on the reaction conditions and the structure of the acyl substituent 2-(5-amino-2-aryl-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles, 2-(5-amino-4-cyano-2,3-dihydrofuran-3-ylidene) propane-dinitrile, 2-amino-4-(dimethoxybenzyl)-6-iodo-5-cyanonicotinamide, 4-amino-6-iodo-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitrile, or 4-amino-6-iodo-3-oxo-1-ethylidene-1,3-dihydrofuro[3,4-c]pyridine-7-carbonitrile are obtained.
Russian Journal of Organic Chemistry | 2012
Ya. S. Kayukov; S. V. Karpov; I. N. Bardasov; O. V. Ershov; M. Yu. Belikov; O. E. Nasakin; O. V. Kayukova
Reactions of aliphatic 2,2,3,3-tetracyanocyclopropyl ketones with aqueous ammonia afforded 4-alkyl- 4-amino-2-oxo-3-azabicyclo[3.1.0]hexane-1,6,6-tricarbonitriles with conservation of the three-membered ring. Reactions of the same compounds with primary amines were accompanied by opening of the cyclopropane ring, and they led to the formation of 5-amino-6,6a-dimethyl-2-oxo-1,2,6,6a-tetrahydropyrrolo[2,3-b]-pyrrole-3,4-dicarbonitriles as a result of successive heterocyclizations.