C 51 Chemistry of O- and C-adducts derived from 1,4-diazinium salts: the use of tetrahydropyrazines in the synthesis of condensed systems [Electronic resource] / G. L. Rusinov, P. A. Slepukhin, V. N. Charushin, O. A. Dyachenko, O. N. Kazheva, A. N. Chekhlov, E. V. Verbitskiy, M. I. Kodess, O. N. Chupakhin // Mendeleev Communications. - 2006. - Vol. 16, № 1. - P26-29 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 1-Ethyl-2,3-dicyano-5-nitromethyl-6-methoxy-1,4,5,6-tetrahydropyrazine reacts with N-methylquinoxalinium iodide in the presence of triethylamine to form octahydro-2,4a,5,10-tetraazabenzo[b]fluorene-3,4-dicarbonitrile, while our attempts to obtain similar polycyclic products from stereoisomeric 5-(S)- and 5-(R)-(1`-nitroprop-1`-yl)-6-methoxy-1,4,5,6-tetrahydropyrazines derived from the reaction of 1-nitropropane with 2,3-dicyano-5,6-dimethoxy-1-ethyl-1,4,5,6-tetrahydropyrazine. \\\\Expert2\\nbo\\Mendeleev Communications\\2006, v.1, p.26.pdf |
A 10 A new approach to incorporate the carboranyl fragment into 2,5-diazabicyclo[2.2.2]oct-2-enes [Electronic resource] / G. L. Rusinov, E. V. Verbitskiy, P. A. Slepukhin, O. N. Zabelina, I. N. Ganebnuikh, V. N. Kalinin, V. A. Ol'shevskaya // Mendeleev Communications. - 2009. - Vol. 19, № 5. - P243-245 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 5-(Het)aryl-2,3-dicyano-1-ethylpyrazinium salts have been established to react with 9-allyl-ortho- and 9-allyl-meta-carboranes in the presence of sodium iodide into carboranylmethyl derivatives of 2,5-diazabicyclo[2.2.2]oct-2-ene \\\\Expert2\\nbo\\Mendeleev Communications\\2009, v.19, p.243.pdf |
R 30 Reactions of radicals generated from 1-ethyl-1,4-diazinium salts: Addition to the C-C triple bond versus dimerization [Text] / G. L. Rusinov, E. V. Verbitskiy, P. A. Slepukhin, O. N. Zabelina, M. I. Kodess, M. A. Ezhikova, V. N. Charushin, O. N. Chupakhin // Heterocycles. - 2009. - Vol. 78, № 9. - P2315-2324 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Radical species generated from 5-aryl-substituted 1-ethyl-2,3-dicyano-1,4-diazinium salts by action of sodium iodide undergo dimerization into [2,2?]bipyrazinyl derivatives, as evidenced by NMR and X-ray crystallography data. The pyrazinyl radicals can also be involved into the addition reaction on the C-C triple bond, thus demonstrating a new synthetic route to modify the structure of pyrazines. The structures of E- and Z-isomers of 1-(1?,2?-dihydropyrazinyl-2?)-2-iodoethenes have been proved by 1H and 13C NMR spectroscopy and X-ray analysis |
S 83 Stereochemical features of addition of O- and C-nucleophiles to 5-(Het)aryl-2,3-dicyano-1-ethylpyrazinium salts [Electronic resource] / E. V. Verbitskiy, G. L. Rusinov, P. A. Slepukhin, A. N. Grishakov, M. A. Ezhikova, M. I. Kodess, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2008. - Vol. 44, № 2. - P302-310 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Stable delta(H)-adducts of O- and C-nucleophiles were obtained with cations of 5-(het)aryl-2,3-dicyano-1-ethylpyrazinium, and their structure was investigated by X-ray diffraction analysis. Analytical separation was performed of 1,2-dihydropyrazines into individual enantiomers by means of HPLC on columns with chiral sorbents \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2008, 44 (2), 302.pdf |
F 56 First example of direct introduction of nucleophiles bearing a stable radical moiety into azaaromatic substrates [Electronic resource] / E. V. Verbitskiy, G. L. Rusinov, P. A. Slepukhin, A. I. Matern, Yu. N. Shvachko, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2006. - Vol. 55, № 11. - P2114-2116 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Addition products of 4-hydroximino-2,2,6,6-tetramethylpiperidine-1-oxyl with 5-aryl-2,3-dicyano-1-ethylpyrazinium salts were isolated for the first time. Crystallographic data on the three-dimensional structures of ?H-adducts bearing a stable radical moiety were obtaned \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2006, 55 (11), 2114.pdf |
T 82 Transformations of C-adducts of 1,4-diazinium salts with dicarbonyl compounds into polycyclic systems [Electronic resource] / E. V. Verbitskiy, P. A. Slepukhin, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 3. - P652-656 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: C-Adducts of 5-(het)aryl-2,3-dicyano-1-pyrazinium salts containing a residue of a 1,3-dicarbonyl compound at position 6 can be involved in the cyclization with hydrazine hydrate giving rise to pyrazino[2,3-c]pyridazines along with the expected pyrazole derivatives. The reactions of the same ?H-adducts with hydroxylamine unexpectedly afforded triazacyclopenta[a]indene derivatives. The crystallographic data on the three-dimensional structures of new polycyclic compounds were obtained \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (3), 652.pdf |
1,3-Dipolar cycloaddition of [(o-carboran-1-yl)methyl]azide to alkynes [Text] / V. A. Ol'shevskaya, E. V. Verbitskiy, G. L. Rusinov, V. N. Kalinin, V. N. Charushin // Doklady Chemistry. - 2010. - Vol. 434, № 2. - P245-248 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HETEROCYCLIC SYSTEMS -- CLOSO-CARBORANES -- CARBORANES \\\\Expert2\\nbo\\Doklady Chemistry\\2010, v. 434, N 1, p. 245-248.pdf |
R 30 Reactions of sigma(H)-adducts of 1-ethyl-1,4-diazinium salts with arylalkynes as a one-step approach to pyrrolo[1,2-a]pyrazine derivatives [Electronic resource] / E. V. Verbitskiy, P. A. Slepukhin, M. A. Ezhikova, M. I. Kodess, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 6. - P1291-1293 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The O- and C-adducts of 5-aryl and 5-hetaryl-2,3-dicyano-1-ethylpyrazinium salts are hidden sources of ylides, which can be used for the cyclization with arylacetylenes giving rise to pyrrolo[1,2-a]pyrazines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (6), 1291-1293.pdf |
S 59 Sigma(H)-Adducts of N-alkylpyrazinium and quinoxalinium salts with nucleophiles. The 1H and 13C NMR spectra and the crystal structures of P-adducts [Electronic resource] / E. V. Verbitskiy, M. V. Berezin, P. A. Slepukhin, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 1. - P176-181 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The previously unknown addition products of P-nucleophiles to 5-aryl- and 5-hetaryl- 2,3-dicyano-1-ethylpyrazinium salts and to 5-aryl- and 5-hetaryl-14nethylquinoxalinium salts were synthesized. The three-dimensional structures of the P- sigma(H)-adducts of the 1,4-diazine series were established by X-ray diffraction \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (1), 176-181.pdf |
E 43 Electrochemical sensor based on metal-containing receptors for urea measurements [Text] : доклад, тезисы доклада / A. Kozitsina [и др.] // International Congress on Analytical Sciences "ICAS - 2006",M., June 25-30 2006 : book of abstracts. - М., 2006. - Vol. 1. - P291 : табл. - Bibliogr. : p. 291 (1 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ |
R 30 Reactions of radicals generated from 1-ethyl-1,4-diazinium salts: addition to the C-C triple bond dimerization [Text] / G. L. Rusinov, E. V. Verbitskiy, P. A. Slepukhin, O. N. Zabelina, M. I. Kodess, M. A. Ezhikova, V. N. Charushin, O. N. Chupakhin // Heterocycles : an International Journal for Reviews and communications in Heterocyclic Chemistry. - 2011. - V. 78, № 9. - P2315-2324 : граф., табл. - Библиогр.: с. 2323-2324 (32 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Radical species generated from 5-aryl-substituted 1-ethyl-2,3-dicyano-1,4-diazinium salts by action of sodium iodide undergo dimerization into [2,2']bipyrazinyl derivatives, as evidenced by NMR and X-ray crystallography data. The pyraziny! radicals can also be involved into the addition reaction on the C-C tziple bond, thus demonstrating a new synthetic route to modify the structure of pyrazines. The structures of E- and Z-isomers of 1-(1',2'-dihydropyrazinyl-2')-2-iodoethenes have been proved by 1H and 13C NMR spectroscopy and X-ray analysis. |
R 30 Reactions of 5-(het)aryl-1-ethyl-2(1H )-pyrazinones with terminal arylacetylenes promoted by microwave radiation / E. V. Verbitskiy, E. M. Cheprakova, P. A. Slepukhin, M. G. Pervova, M. A. Samorukova, O. N. Zabelina, G. L. Rusinov, V. N. Charushin // Chemistry of Heterocyclic Compounds. - 2011. - Vol. 47, № 6. - P710-718. - Bibliogr. : p. 718 (13 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ARYLACETYLENES -- MICROWAVE RADIATION -- IONIC LIQUID Аннотация: The reaction of 5-(het)aryl-1-ethyl-2(1H)-pyrazinones with terminal arylacetylenes, leading to a mixture of two isomeric 4-aryl- and 5-aryl-substituted 2(1H)-pyridones has been investigated. The regioselectivity of this reaction has been shown on the basis of reaction mixtures study by chromato-mass spectrometry. A crystallographic investigation of the synthesized 2(1H)-pyridones and also a forecast of their potential biological activity have been carried out \\\\Expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2011, v.47, N 6, p.710-718.pdf |
M 65 Microwave-promoted reactions of 5-(het)-aryl-1-ethyl-2(1h)-pyrazinones with terminal arylacetylenes / E. V. Verbitskiy, E. M. Cheprakova, P. A. Slepukhin, I. G. Pervova, M. A. Samorukova, O. N. Zabelina, G. L. Rusinov, V. N. Charushin // Chemistry of Heterocyclic Compounds. - 2011. - № 6. - С. 860-870 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRAZINONES -- ARYLACETYLENES |
C 73 Combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen (HSN) reactions as a versatile route to pyrimidines bearing thiophene fragments / E. V. Verbitskiy, E. M. Cherprakova, P. A. Slepukhin, M. I. Kodess, M. A. Ezhikova, M. G. Pervova, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Tetrahedron. - 2012. - Vol.68, №27-28. - С. 5445-5452 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SUZUKI–MIYAURA -- CROSS-COUPLING -- PYRIMIDINES Аннотация: It has been shown that combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen is a versatile method for the synthesis of 4-(thiophen-2-yl)-, 5-(thiophen-2-yl)-, and 4,5-di(thiophen-2-yl) substituted pyrimidines from the commercially available 5-bromopyrimidine. The HSN (AE)- and HSN (AO)-reactions of 5-bromopyrimidine with thiophene and 2-bromothiophene have been studied by gas–liquid chromatography/mass-spectrometry. The structures of intermediate σH-adducts, as well as thiophene-(thiophenyl)pyrimidine and bithiophene-(thiophenyl)pyrimidine dyads have first been established by X-ray crystallography analysis \\\\Expert2\\nbo\\Tetrahedron\\2012, v. 68, p. 5445.pdf |
σH-Adducts of 1-alkyl-1,4-diazinium salts as the sources of biradicals in the synthesis of tetraazaphenanthrenes / E. V. Verbitskiy, P. A. Slepukhin, M. A. Ezhikova, M. I. Kodess, Yu. N. Shvachko, D. V. Starichenko, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 975-980 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PH-ADDUCTS -- BIRADICALS -- TETRAAZAPHENANTHRENES Аннотация: O- and C-Adducts of 5-(het)aryl-2,3-dicyano-1-ethylpyrazinium salts are latent sources of biradicals capable of forming tetraazaphenanthrene derivatives via dimerization. The mechanisms of the reactions were examined using ESR spectroscopy. The stereochemistry of the resulting heterocyclic systems was studied by NMR spectroscopy. The crystallographic data on their three-dimensional structures were obtained \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2011, 60 (5), 975-980.pdf |
C 75 Consecutive S-N(H) and Suzuki–Miyaura Cross-Coupling Reactions – an Efficient Synthetic Strategy to Pyrimidines Bearing Pyrrole and Indole Fragments / E. V. Verbitskiy, G. L. Rusinov, V. N. Charushin, O. N. Chupakhin, E. M. Cheprakova, P. A. Slepukhin, M. G. Pervova, M. I. Kodess // European Journal of Organic Chemistry. - 2012. - Vol. 2012, №33. - С. 6612-6621 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHETIC METHODS -- CROSS-COUPLING -- NITROGEN HETEROCYCLES Аннотация: The combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen reactions is a versatile tool for the syntheses of 4-(1R-pyrrol-2-yl)- and 4-(1R-indol-3-yl)-5-(hetero)aryl-substituted pyrimidines from commercially available 5-bromopyrimidine. The SNH [AE, (addition–elimination)] and SNH [AO, (addition–oxidation)] reactions of 5-bromopyrimidine with pyrroles and indoles were studied by gas chromatography–mass spectrometry. The structures of the intermediate σH adducts as well as the pyrrole-(hetero)arylpyrimidine and indole-(hetero)arylpyrimidine dyads were established for the first time by X-ray crystal structure analysis \\\\Expert2\\nbo\\European Journal of Organic Chemistry\\2012, p.6612.pdf |
N 89 Novel bis[(1,2,3-triazolyl)methyl]carborane derivatives via regiospecific copper-catalyzed 1,3-dipolar cycloaddition / V. A. Ol'shevskaya, E. V. Verbitskiy, G. L. Rusinov, V. N. Charushin, Evamarie Hey-Hawkins // Polyhedron. - 2012. - Vol.42, №1. - С. 302-306 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CARBORANES -- CARBABORANES -- TRIFLATES Аннотация: 1,2-Bis(azidomethyl)-о-carborane and 1,7-bis(azidomethyl)-m-carborane, prepared from the corresponding carboranylmethyl triflates and sodium azide, were conveniently functionalized by azide–alkyne cycloaddition affording novel bis[(1,2,3-triazolyl)methyl]carborane derivatives. Regiospecificity of this process was achieved by employing copper(II) acetate hydrate. Reaction of bis[(1,2,3-triazolyl)methyl]carborane derivatives with MeI yielded 3-methyl-1,2,3-triazolium carborane salts \\\\Expert2\\nbo\\Polyhedron\\2012. v.42. p.302.pdf |
R 30 Reactions of pyrazinium salts with phenols:from σH-adducts to SN Hproducts and transformations into benzo[b]furans / E. V. Verbitskiy, Yu. A. Kvashnin, P. A. Slepukhin, A. V. Kuchin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushina // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 919-928 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DIHYDROPYRIDINES -- NUCLEOPHILIC SUBSTITUTION -- HYDROGEN Аннотация: The reaction of 5-(het)aryl-2,3-dicyano-1-ethylpyrazinium salts with phenol derivatives affords relatively stable dihydropyrazines, whereas the reactions of 6-(het)aryl-1,2,5-oxadiazolo[3,4-b]pyrazin-4-ium protic salts, depending on the phenol structure, result in products of nucleophilic substitution of hydrogen or open-chain transformation products: benzo[b]furan-substituted derivatives. The crystallographic data on the spatial structure of all types of the synthesized products were obtained \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2011, 60 (5), 919-928.pdf |
S 98 Synthesis, crystal structures, and properties of 5-(het)aryl-3-cyano-1-ethyl-2(1H)-pyr / E. V. Verbitskiy, M. V. Berezin, P. A. Slepukhin, O. N. Zabelina, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 906-913 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- PYRAZINONES -- CRYSTAL STRUCTURES Аннотация: A simple method for the synthesis of 5-(het)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones was proposed. The method is based on the hydrolysis of the corresponding 2,3-dicyanopyrazinium salts. The spectral properties of pyrazinones were studied and their crystallographic investigation was carried out. The possibility of introduction of 5-(het)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones into the [2+4] cycloaddition under the microwave activation conditions was sho \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2011, 60 (5), 906-913.pdf |
M 65 Microwave-assisted palladium-catalyzed C–C coupling versus nucleophilic aromatic substitution of hydrogen (SNH) in 5-bromopyrimidine by action of bithiophene and its analogues [Электронный ресурс] / E. V. Verbitskiy, E. M. Cheprakova, E. F. Zhilina, M. I. Kodess, M. A. Ezhikova, M. G. Pervova, P. A. Slepukhin, V. N. Charushin // Tetrahedron. - 2013. - Vol.69, №25. - P5164-5172 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): C–H BOND ACTIVATIONS -- PYRIMIDINES -- PALLADIUM Аннотация: 5-Bromopyrimidine reacts with 2,2′-bithiophene, [2,2′:5′,2″]terthiophene and 2-phenylthiophene in the presence of a palladium catalyst to give 5-(het)aryl substituted pyrimidines due to the palladium-catalyzed aryl–aryl C–C coupling. However 5-bromo-4-(het)aryl-pyrimidines have been prepared from the same starting materials through the SNH-reaction catalyzed by a Lewis acid. Conditions for both types of reactions were optimized. All components of the reaction mixtures, including by-products, have been elucidated by gas–liquid chromatography/mass-spectrometry. Evidence for the structure of 4- and 5-bithiophenyl-substituted pyrimidines has first been obtained by means of X-ray crystallography analysis. Molecular orbital calculations (TDDFT), as well as the redox and optical measurements for all new compounds have also been performed \\\\Expert2\\NBO\\Tetrahedron\\2013, v. 68, p. 5164.pdf |