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1.
Инвентарный номер: нет.
   
   A 53


   
    An- и Sn - реакции в 1.2,4 - триазинах в синтезе новых супрамолекулярных соединений [] / О. Н. Чупахин, Г. Л. Русинов, Н. А. Ициксон, Д. Г. Береснев // Актуальные проблемы химии и технологии органических веществ. История, проблемы органического синтеза, перспективы : сб. науч. тр. / РАН, УрО, Ин-т орган. синтеза. - Екатеринбург, 2002. - С. 308-321 : рис. - Библиогр. : с. 319-321 (18 назв.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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2.
Инвентарный номер: нет.
   


    Chupakhin, O. N.
    Application of electrochemical oxidative methods in the C(SP2)–H functionalization of heterocyclic compounds / O. N. Chupakhin, A. V. Shchepochkin, V. N. Charushin // Advances in heterocyclic chemistry. - 2020. - Т. 131. - P1-47
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
C-H FUNCTIONALIZATION -- ELECTROCHEMICAL OXIDATION -- GREEN CHEMISTRY -- OCDC -- SN H REACTIONS
Аннотация: New atom-economic and environmentally friendly processes should replace the traditional ways of building C–C, C–N, C–O, C–P, C–S bonds, which are usually based on the replacement of a halogen atom, and, therefore, required the preliminary modification of substrates, and the use of aggressive reagents, harsh conditions or expensive catalysts. In recent years, the direct metal-free functionalization of the C(sp2)–H bond, which provides the most efficient and low-waste pathway for molecular transformation, has attracted increasing attention. However, these transformations usually require stoichiometric amounts of chemical oxidizing agents. The modern world and its sustainable development trends are forcing the chemical industry to improve in an environmentally friendly direction and meet the requirements of “green chemistry.” In this regard, the use of electrochemical methods is extremely important. Electrochemical anodic oxidation is an ideal option for the replacement of chemical oxidizers in C–H functionalization reactions. The data on the main electrochemical methods and approaches used for the direct functionalization of the C(sp2)–H bond in heterocyclic compounds are classified and summarized in this paper.

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3.
Инвентарный номер: нет.
   
   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
ББК 24
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.

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4.
Инвентарный номер: нет.
   
   D 62


   
    Direct C—C-coupling of ferrocenyl- and cymantrenyllithium [Electronic resource] / I. A. Utepova, A. A Musikhina, Yu. A. Kvashnin, M. A. Shcherbakova, P. O. Serebrennikova, G. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №12. - С. 2531-2535. - Bibliogr. : p. 2535 (15 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
FERROCENYLLITHIUM -- CYMANTRENYLLITHIUM -- HYDROGEN
Аннотация: A direct C—C coupling of ferrocenyl and cymantrenyllithium with 5 (het)aryl 1,2,5 oxadiazolo[3,4 b]pyrazines was accomplished. Main characteristics of the SN H reaction prod ucts were obtained, as well as crystallographic data on the spatial structure of oxadiazolopyr azinylferrocenes and cymantrenes synthesized

\\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (12), 2531-2535.pdf
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5.
Инвентарный номер: нет.
   
   H 10


   
    H-1 and C-13-NMR investigations on-adduct formation of 1,2,4-triazine 4-oxides and 3-chloro-6-phenyl-1,2,4-triazine with liquid ammonia and alkylamines [Text] / A. Rykowski, O. N. Chupakhin, D. N. Kozhevnikov, V. N. Kozhevnikov, V. L. Rusinov, der Plas H. C. Van // Heterocycles. - 2001. - Т. 55, № 1. - P127-133
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: 1H- and 13C-NMR spectra of the ?-adducts formed between 6-phenyl-1,2,4-triazine 4-oxide (1a), 3-ethyl-6-phenyl-1,2,4-triazine 4-oxide (1b) and liquid ammonia, methylamine or dimethylamine are described, together with 1H NMR spectra of 3-chloro-6-phenyl-1,2,4-triazine (7) in liquid ammonia. The results of the NMR study have shown that the carbon C-5 in 1a-b and 7 is the preferred site for nucleophilic attack by liquid ammonia and alkylamines at low temperatures (from -75° to -20°C). The ?-adduct (5e) formed between 1a and dimethylamine at -75°C on heating to -20°C irreversibly converts to open-chain product (3a), via intermediary C-3 ?-adduct (6). The amination of 7 into 3-amino-6-phenyl-1,2,4-triazine (10) occurs via SN(AE) mechanism involving the isomerisation of the C-5 ?-adduct (8) into the C-3 ?-adduct (9) as confirmed by a 15N study with labeled liquid ammonia.

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6.
Инвентарный номер: нет.
   
   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
ББК 54
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
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7.
Инвентарный номер: нет.
   


   
    Novel pentafluorophenyl- and alkoxyphenyl-appended 2,2'-bipyridine push-pull fluorophores: a convenient synthesis and photophysical studies / T. D. Moseev, E. A. Nikiforov, M. V. Varaksin [et al.] // Synthesis. - 2021. - Vol. 53, № 19. - P3597-3607
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
2,2′-BIPYRIDINES -- 1,2,4-TRIAZINES -- POLYFLUOROARENES
Аннотация: A convenient method for the synthesis of new highly in non-polar solvents soluble photoactive pentafluorophenyl-substituted and extended alkoxyphenyl-substituted 2,2′-bipyridines is reported. The synthetic strategy for the preparation of such ligands involves a sequence of several structural transformations, such as O-alkylation, nucleophilic substitution of hydrogen (SN H) in 1,2,4-triazine precursors via the ‘addition–elimination’ scheme, and the subsequent conversion of the obtained 1,2,4-triazines into 2,2′-bipyridines by means of the aza-Diels–Alder reaction. The photophysical properties of the synthesized novel pentafluoroaryl-substituted 2,2′-bipyridines were comprehensively studied. The obtained photophysical data indicate the competitive advantages of the herein reported pentafluoroarylated push–pull fluorophores, bearing extended aliphatic moieties, over their analogues containing benzoxy or phenolic fragments in terms of improvement in quantum yield and well-pronounced positive solvatochromism confirmed by the mathematical analysis according to the Lippert–Mataga equation.

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8.
Инвентарный номер: нет.
   
   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
ББК 54
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
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9.
Инвентарный номер: нет.
   
   R 30


   
    Reactivity of polychlorinated biphenyls in nucleophilic and electrophilic substitutions [Electronic resource] / T. I. Gorbunova, J. O. Subbotina, V. I. Saloutin, O. N. Chupakhin // Journal of Hazardous Materials. - 2014. - Vol.278. - С. 491-499. - Bibliogr. : p. 498-499 (58 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CONGENERS -- DESCRIPTORS -- ELECTROPHILIC SUBSTITUTION
Аннотация: To explain the chemical reactivity of polychlorinated biphenyls in nucleophilic (SN) and electrophilic (SE) substitutions, quantum chemical calculations were carried out at the B3LYP/6-31G(d) level of the Density Functional Theory in gas phase. Carbon atomic charges in biphenyl structure were calculated by the Atoms-in-Molecules method. Chemical hardness and global electrophilicity index parameters were determined for congeners. A comparison of calculated descriptors and experimental data for congener reactivity in the SN and SE reactions was made. It is shown that interactions in the SN mechanism are reactions of the hard acid-hard base type, these are the most effective in case of highly chlorinated substrates. To explain the congener reactivity in the SE reactions, correct descriptors were not established. The obtained results can be used to carry out chemical transformations of the polychlorinated biphenyls in order to prepare them for microbiological destruction or preservation

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10.
Инвентарный номер: нет.
   
   S 69


   
    S-N(H) reactions of 3-fluoronitroarenes with chloromethyl sulfone as the method for the construction of 6-fluoro-3-sulfonylindoles [Electronic resource] / G. A. Zhumabaeva, S. K. Kotovskaya, N. M. Perova, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2007. - Vol. 56, № 10. - P2048-2053
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: 5-R-6-Fluoro-3-phenylsulfonylindoles were synthesized by the SN(H) reaction of 3-fluoronitrobenzenes with chloromethyl phenyl sulfone in DMSO in the presence of KOH with subsequent reduction of the nitro group and intramolecular cyclization of imidates

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2007, 56 (10), 2048.pdf
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