F 70 Fluorine-containing heterocycles. XV. Reactions of polyfluorobenzoyl isothiocyanates with amino azines and amino azoles [Electronic resource] / E. V. Nosova, G. N. Lipunova, A. A. Laeva, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 10. - P1544-1550. - Библиогр. : с. 1550 (9 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of tetra-and pentafluorobenzoyl isothiocyanates with aminoazoles and aminoazines led to the formation of fluorinated 1,3-benzothiazin-4-ones which reacted with cyclic amines in different ways. Replacement of the N=C=S fragment was observed in some reactions of polyfluorobenzoyl isothiocyanates with nucleophiles. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (10), 1544.pdf |
N 52 New method for the annelation of the pyridine fragment to azines [Electronic resource] / V. N. Charushin, A. M. Boguslavskii, M. G. Ponizovskii, M. I. Kodess, A. N. Chekhlov, Sh. G. Mkoyan, S. M. Aldoshin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1267-1271 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reaction of quinoxaline-2-carbaldehyde with ethyl (E)-3-aminocrotonate afforded ethyl 4-oxo-1,4-dihydropyrido[2,3-b]quinoxaline-3-carboxylate, which is a structural analog of nalidixic and 4-quinolone-3-carboxylic acids representing the basis of the known antibacterial drugs of the fluoroquinolone series \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1267.pdf |
F 70 Fluorinated azines and benzazines containing oxygen or sulfur atoms [Text] / E. V. Nosova, G. N. Lipunova, V. N. Charushin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2010. - Vol. 131, № 12. - P1267-1288 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: In the frames of this review article the recently obtained data on synthetic approaches to fluorinated oxa(thia)azines and benzazines, their chemical properties, structure, and biological activity have been analyzed \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2010, v. 131, p.1267.pdf |
T 44 The C-C coupling of ferrocenes with electron-deficlent azaaromatics - a new route for construction of heterocyclic ligands and complexes [] / O. N. Chupakhin, I. S. Kovalev, I. A. Utepova, V. L. Rusinov, V. N. Charushin // 20-th International Congress of Heterocyclic Chemistry, Palermo, July 31-August 5, 2005 : book of abstracts . - Palermo, Italy, 2005. - С. 507. - Библиогр.: с. 507 (3 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ |
S 98 Synthesis of chiral ferrocenylazines. Negishi cross-coupling or S N H reactions? [Electronic resource] / A. A Musikhina, I. A. Utepova, N. S. Serebryakov, O. N. Chupakhin, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2013. - Vol.49, №8. - С. 1191-1194. - Bibliogr. : p. 1194 (28 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- CHIRAL FERROCENYLAZINES -- NEGISHI Аннотация: Preparation of new hetaryl-containing planar chiral ferrocene by a nucleophilic substitution of hydrogen in azines was performed using a lithium derivative of (S)-ferrocenyl-p-tolylsulfoxide as s nucleophilic reagent \\\\expert2\\NBO\\Russian Journal of Organic Chemistry\\2013, 49, (8), 1191-1194.pdf |
S 98 Synthesis of new meso-substituted heterocyclic calix[4]arenes via SN H approach [Electronic resource] / M. V. Varaksin, I. A. Utepova, G. N. Chupakhin, V. N. Charushin // Macroheterocycles . - 2013. - Vol.6, №4. - С. 308-314. - Bibliogr. : p. 313-314 (42 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINES -- C-C COUPLING -- CALIX[4]ARENES Аннотация: An effective synthetic approach to heterocyclic derivatives of meso-substituted calixarenes has been suggested by using the SN H methodology based on the direct, non-catalyzed by transition metals, C-C coupling of 1,2,4-triazines with the lithium salts of tetramethoxycalix[4]arenes \\\\expert2\\NBO\\Macroheterocycles\\2013.6.4.308-314.pdf |
D 62 Direct Nucleophilic Functionaliation of Arines and their N-Oxidesby Lithiumaldonitrones / S. V. Mikhaylov, M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Уральский научный форум "Современные проблемы органической химии". XVII Молодежная школа-конф. по органической химии, Екатернинбург, 8-12 июня 2014 г. : сб. тез. - Екатеринбург, 2014. - С. 238. - Bibliogr. : p. 238 (3 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINES -- LITHIUMALDONITRONES -- HETEROCYCLIC COMPOUNDS |
T 98 Two Approaches in the Synthesis of Planar Chiral Azinylferrocenes [Electronic resource] / I. A. Utepova, O. N. Chupakhin, P. O. Serebrennikova, A. A Musikhina, V. N. Charushin // Journal of Organic Chemistry. - 2014. - Vol. 79, № 18. - С. 8659-8667. - Bibliogr. : p. 8666-8667 (34 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHIRAL AZINYLFERROCENES -- CROSS-COUPLING REACTION -- HALOGENATED AZINES Аннотация: Two synthetic routes to the chiral azinylferrocenes (CAFs) 5 and 15, key intermediates for the synthesis of new enantiomerically enriched P,N-ligands, have been compared. The first approach is based on the palladium-catalyzed cross-coupling reaction of halogenated azines with organozinc derivatives of ferrocenes (the Negishi reaction). The second approach exploits a new synthetic methodology, which provides a shorter pathway, through the direct C–H functionalization of aromatics by the C–C coupling of halogen-free (hetero)arenes with lithium ferrocenes bearing stereogenic C and S atoms. The palladium complexes of P,N-ligands have been used as catalysts for the Tsuji–Trost reaction, which proceeds with high enantioselectivity to give allylic substitution products in good yields. \\\\expert2\\nbo\\Journal of Organic Chemistry\\2014, v.79, p.8659.pdf |
M 45 Mechanism of nucleophilic substitution of hydrogen in azines IV. Role of one-electron transfer in reactions with arylamines / O. N. Chupakhin, V. N. Charushin, I. M. Sosonkin, E. G. Kovalev, G. L. Kalb, I. Ya. Postovskii // Chemistry of Heterocyclic Compounds. - 1977. - Vol. 13, № 5. - P562-566. - Bibliogr. : p. 566 (28 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): N-METHYLAZINIUM -- BENZOANNELATION EFFECT -- ELECTROPHILIC CATIONS Аннотация: A satisfactory correlation between the polarographic reduction potentials and the calculated energies of the lower vacant molecular orbitals was found for a number of N-methylazinium cations. The result of the aza effect and the benzoannelation effect is a shift of the reduction potentials to the positive region by 0.2-0.5 and 0.2-0.7 V, respectively. Electron transfer from N,N,N′,N′-tetramethyl-p-phenylenediamine to the most electrophilic cations was recorded. The possibility of the occurrence of reactions involving aminoarylation of the acridinium cation via a one-electron mechanism was demonstrated electrochemically and by model reactions |
C 47 Charushin, V. N. Cyclization of azines with bifunctional nucleophiles — a one-step route to condensed heterocycles (review) [Electronic resource] / V. N. Charushin, M. G. Ponizovskii, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 1985. - Vol. 21, № 8. - С. 839-853. - Bibliogr. : p. 851-853 (115 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BIFUNCTIONAL REAGENTS -- HETEROCYCLES Аннотация: Nucleophilic diaddition and disubstitution in the azine. series with the participation of bifunctional reagents, the result of which is the formation of condensed heterocycles, were examined. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1985, v.21, N 8, p. 839.pdf |
C 57 Chupakhin, O. N. Nucleophilic substitution of hydrogen in azines [Electronic resource] / O. N. Chupakhin, V. N. Charushin, H. C. Van der Plas // Tetrahedron. - 1988. - Vol. 44, № 1. - С. 1-34. - Bibliogr. : p. 32-34 (186 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINES -- HYDROGEN \\\\expert2\\nbo\\Tetrahedron\\1988, v. 44, p. 1-34.pdf |
C 47 Charushin, V. N. Reactions of Azines with Bifunctional Nucleophiles: Cyclizations and Ring Transformations [Electronic resource] / V. N. Charushin, O. N. Chupakhin, H. C. Van der Plas // Advances in Heterocyclic Chemistry. - 1988. - Vol. 43 (C). - С. 301-353. - Bibliogr. : p. 347-353 (200 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINES -- BIFUNCTIONAL REAGENTS -- CYCLOADDUCTS Аннотация: Reactions of azines with bifunctional nucleophiles can give rise to several cycloadducts, the structure depending on the nature of reagents, the structure of the azine substrate, and the reaction conditions. Three types of cycloadducts are proposed to be formed in reactions of azines with such 1,3-N,C-dinucleophiles as acetamidines and acetimino esters. Ortho-cyclization products can usually be isolated, while meta- and para-bridged cycloadducts are unstable and are often transformed into other heterocyclic systems. Their presence as intermediates can, however, often is rationalized by spectroscopic methods or 15N-labeling studies. Many of the reactions discussed provide a very convenient synthetic route to a great variety of azine derivatives. It seems to be a very interesting and promising area of heterocyclic chemistry and there is no doubt that further investigations into this field also allow new syntheses of useful compounds to be developed \\\\expert2\\nbo\\Advances in Heterocyclic Chemistry\\1988. V. 43 (C). P. 301-353.pdf |
D 62 Direct nuclophilic C-H functionalization of azines and their N-oxides by lithium derivatives of aldonitrones [Electronic resource] / M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Tetrahedron. - 2015. - Vol. 71, №38. - С. 7077-7082. - Bibliogr. : p. 7082 (23 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DIPOLE-STABILIZED CARBANIONS -- ORGANIC-SYNTHESIS -- CHEMICAL-PROPERTIES; Аннотация: Novel ligands of the azine family for complexing with metals have been obtained as a result of the uncatalyzed C-C coupling reactions of quinoline, quinoxaline, 1,10-phenantroline, and their N-oxides with (1-oxido-3-phenyl-1,4-diazaspiro[4.5]deca-1,3-dien-2-yl)lithium \\\\expert2\\nbo\\Tetrahedron\\2015, v. 71 , p. 7077-7082.pdf |
A 23 Aerobic oxidative C-H/C-H coupling of azaaromatics with indoles and pyrroles in the presence of TiO2 as a photocatalyst [Electronic resource] / I. A. Utepova, M. A. Trestsova, O. N. Chupakhin, V. N. Charushin, A. A. Rempel // Green Chemistry. - 2015. - Vol. 17, № 8. - С. 4401-4410. - Bibliogr. : p. 4409-4410 (30 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BOND ACTIVATION -- INHIBITORS -- HYDROGEN Аннотация: In this paper we wish to report a highly selective and benign method for the double C-H/C-H coupling of azaaromatics with indoles or pyrrole in the presence of air oxygen/TiO2, as an effective photocatalytic oxidative system. It has been shown that this versatile approach can be applied for direct C-H functionalisation of a variety of azaaromatic systems, such as mono-, di- and triazines, substituted and unsubstituted azines and their benzo-annelated analogues. \\\\expert2\\nbo\\Green Chemistry\\2015, v.17, N 8, p.4401-4410.pdf |
O-72 Organolithium compounds in the nucleophilic substitution of hydrogen in arenes and hetarenes [Electronic resource] / I. S. Kovalev, D. S. Kopchuk, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Russian Chemical Reviews. - 2015. - Vol. 84, № 12. - С. 1191-1225. - Bibliogr. : p. 1224-1225 (237 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NUCLEOPHILIC SUBSTITUTION -- HYDROGEN -- ARENES AND HETARENES Аннотация: The review considers the most typical examples of the direct non-activated non-catalytic C–C bond formation in arenes and their metal complexes activated by electron-withdrawing substituents in the aromatic nucleus and in hetarenes (azines and their N-oxides, porphyrins, etc.) upon the reactions with aliphatic and (hetero)aromatic (hetero)organolithium nucleophiles. Particular attention is given to the direct introduction of nitroxide radicals and (hetero)organic moieties into mono-, di- and triazines and their N-oxides. The influence of the structures of the (hetero)aromatic substrate and the (hetero)organolithium nucleophile on the reaction pathway and rate and on the structure of the reaction product is analyzed. \\\\expert2\\nbo\\Russian Chemical Reviews\\2015, V.84, N12, p. 1191-1225.pdf |
C 47 Charushin, V. N. The Reactions of Azines on Treatment with 1,3-Bifunctional Nucleophiles [Electronic resource] / V. N. Charushin, O. N. Chupakhin // Russian Chemical Reviews. - 1984. - Vol. 53, № 10. - P956-970. - Bibliogr. : p. 969-970 (152 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINES -- 1,3-BIFUNCTIONAL NUCLEOPHILES -- FURAN -- PYRROLE -- IMIDAZOLE Аннотация: The literature data on the o-cyclisation reactions of azines with 1,3-bifunctional nucleophiles, which make it possible to annelate furan, pyrrole, imidazole, and other five-membered rings to an aromatic aza-ring are surveyed and described systematically. The cyclisation reactions leading to m-linked cyclic adducts or products of the transformation of azines via the intermediate formation of cyclic m- and p-adducts are also examined. \\\\expert2\\nbo\\Russian Chemical Reviews\\1984, V.53, N10, p. 956-970.pdf |
C 10 C-H functionalization of azines. Anodic dehydroaromatization of 9-(hetero)aryl-9,10-dihydroacridines [Electronic resource] / A. V. Shchepochkin, O. N. Chupakhin, V. N. Charushin, D. V. Steglenko, V. I. Minkin, G. L. Rusinov, A. I. Matern // RSC Advances. - 2016. - Vol. 6, № 81. - С. 77834-77840 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HYDRIDE TRANSFER-REACTIONS -- AROMATIC-SUBSTITUTION -- NUCLEOPHILIC-SUBSTITUTION Аннотация: Data on anodic dehydroaromatization of 9,10-dihydroacridines, bearing aryl and heteroaryl fragments, are presented. Effects of both electron-donating and electron-withdrawing substituents on the current-voltage characteristics of these compounds have been established. The experimental data proved to be in a good agreement with quantum chemical calculations. A simple and convenient method for the electrochemical conversion of dihydroacridines into the corresponding 9-(hetero)aryl-N-methylacridinium salts has been advanced \\\\expert2\\NBO\\RSC Advances\\2016. Vol. 6, N 81. P. 77834.pdf |
D 62 Direct C-Li/C-H coupling of pentafluorophenyl lithium with azines - an atom- and step-economical strategy for the synthesis of polyfluoroaryl azaaromatics / M. V. Varaksin, T. D. Moseev, V. N. Charushin, O. N. Chupakhin // Journal of organometallic chemistry. - 2018. - Vol. 867. - P278-283 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINE-N-OXIDES -- AZINES -- C-C COUPLING -- C-H FUNCTIONALIZATION -- PENTAFLUOROPHENYL LITHIUM Аннотация: The SN H methodology has successfully been applied for the direct C(sp2)-H functionalization of azaaromatics through the C-Li/C-H coupling of pentafluorophenyl lithium with azines and their N-oxides. As a result, a number of novel fluorinated biheterocyclic ensembles, that are of interest in the design of bioactive molecules and advanced materials, have been prepared in good to excellent yields under rather mild condition. |
Direct c-li/c-h coupling of c6f5li with azines and azoles n-oxides as efficient approach toward to polyfloorinated azaheterocycles / T. D. Moseev, M. V. Varaksin, E. A. Virlova [et al.] // Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - P276-277 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): C-C COUPLING -- NUCLEOPHILIC SUBSTITUTION OF HYDROGEN -- FLUORINE -- FLUORARENES |
Synthesis of meso-substituted calix[4]arenes via reaction of nucleophilic substitution of hydrogen (snh) in azine or azine-n-oxides / T. D. Moseev, M. V. Varaksin, I. A. Lavrinchenko [et al.] // Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - P273-274 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CALIX[4]ARENES -- AZINES -- C-C COUPLING -- NUCLEOPHILIC SUBSTITUTION OF HYDROGEN |