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1.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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2.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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3.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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4.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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5.
Инвентарный номер: нет.
   
   A 89


   
    Asymmetric Reactions of a Series of Aromatic Azines with Nucleophiles / I. N. Egorov, T. A. Tseitler, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin // Heterocycles. - 2012. - Vol.86, №2. - С. 821-889
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
NUCLEOPHILIC ADDITION -- AZINE SERIES -- STEREOSELECTIVE FORMATION
Аннотация: Current review is devoted to the reactions of nucleophilic addition in azine series, leading to the stereoselective formation of optically active products. Three types of reactions are reviewed: the reactions of achiral nucleophiles with chiral azines; the reactions of chiral nucleophiles with achiral azines; reactions of achiral nucleophiles with achiral azines in the presence of chiral catalysts

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6.
Инвентарный номер: нет.
   
   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.)
ББК 54
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

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7.
Инвентарный номер: нет.
   
   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.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
AZINES -- LITHIUMALDONITRONES -- HETEROCYCLIC COMPOUNDS

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8.
Инвентарный номер: нет.
   


   
    New naphtho[1,8-ef]perimidines: synthesis, fluorescence studies and application for detection of nitroanalytes / I. L. Nikonov, L. K. Sadieva, M. I. Savchuk [et al.] // Chimica Techno Acta. - 2021. - Vol. 8, № 4. - Ст. 20218416
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
NAPHTHO[1,8-EF]PERIMIDINES -- FLUORESCENCE -- SENSOR -- EXPLOSIVES
Аннотация: A rational approach to the synthesis of substituted naphtho[1,8-ef]perimidines based on SNH methodology and cyclization reaction in the series of condensed azines with naphthalene substituents was presented. Photophysical properties of the obtained fluorophores were studied, in particular, green fluorescence in the 485–536 nm range with quantum yield up to 32.4% was detected. HOMO-LUMO energy values and distributions for the new compounds were calculated by the DFT method in comparison with nitroanalytes and perylene. Based on the data obtained, as well as on the results of fluorescence titration, the possibility of using the new diazaperylenes as potential chemosensors for the visual detection of nitro-containing explosives was shown.

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9.
Инвентарный номер: нет.
   


   
    Oxidizing agents in metal-catalyzed and metal-free C-H functionalization of heteroarenes / I. A. Utepova, O. N. Chupakhin, M. A. Trestsova [et al.] // Arkivoc. - 2021. - № 9. - P240-299
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
DIRECT С-H FUNCTIONALIZATION -- HETEROARENE -- OXIDIZING AGENTS
Аннотация: Oxidative C-H functionalization represents a crucial method to make new C-C, C-X (X = heteroatom) bonds. An optimal selection of the oxidizing agent goes hand in hand with the insight into the reaction mechanism. This review covers recent advances in methods of direct oxidative C-H functionalization of azines and their derivatives with heteroaromatic nucleophiles. Also we review the data on application of inorganic and organic oxidants for implementation of these reactions. C-H functionalizations under electrochemical and photocatalytic oxidation conditions are included as well.

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10.
Инвентарный номер: нет.
   


   
    Synthesis and properties of azines functionalized graphene with extremely high adsorptive ability to Eu3+ ions / O. N. Chupakhin, A. A Musikhina, I. A. Utepova [et al.] // Flatchem. - 2022. - Vol. 33. - P100348
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: In this work, a versatile synthetic protocol for obtaining of new promising carbon materials based on the C–C coupling of graphenide lithium species with azaaromatic compounds (1,10-phenanthroline, phenyl-1,2,5-oxadiazolo[3,4-b]pyrazine) has been suggested. It was shown that more electrophilic oxadiazolopyrazine gave the product with high degree of graphene functionalization and demonstrated non-isomorphic properties. At the same time, phenanthrolinyl graphene has less functionalization degree due to a lower electrophilicity of azine. However, the large size of pores between organic residues in phenanthrolinyl graphene allows adsorbing almost 10% of Eu3+. The mesurment of adsorption isotherm showed an extremely high affinity of phenanthrolinylgraphene to Eu (III) ions in netural or alkaline conditions, and the obtained hybrid material could work at least 5 sorption/desorption cycles. The structures of azine-graphene dyads were verified by complex of modern physicochemical analyses methods (the Raman spectroscopy, FTIR, XPS, SEM, EDS and TGA analyses).

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11.
Инвентарный номер: нет.
   


   
    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

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12.
Инвентарный номер: нет.
   
   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
ББК 54
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
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13.
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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14.
Инвентарный номер: нет.
   


   
    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

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15.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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16.
Инвентарный номер: нет.
   
   D 62


   
    Direct introduction of heterocyclic units into porphyrin derivatives [Electronic resource] / O. N. Chupakhin, G. L. Rusinov, D. G. Beresnev, S. Sh. Bashirov, M. G. P. M. S. Neves, J. A. S. Cavaleiro // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 1. - P160-163 : ил. - Библиогр.: с. 163 (10 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
1,2,4-TRIAZHIES -- HETERYLPORPHYRINS -- MESO-TETRAARYLPORPHYRINS -- NONSYMMETRICAL PORPHYRINS -- QUINAZOLINE
Аннотация: In the reaction with quinazoline and 5-phenyl-1,2,4-triazin-5(2H)-one, 5,10,15,20-tetra(4-methoxyphenyl)porphyrin exhibits nucleophilic properties. In quinazoline excess, C-C coupling occurs at the C=N bond of azines and position 3 of the aryl ring to form 5,10,15,20-tetrakis(3-heteryl-4-methoxyphenyl) porphyrins. Monoheteryl-substituted porphyrin was obtained by the reaction of equimolar amounts of 5,10,15,20-tetra(4-methoxyphenyl)porphyrin and 5-phenyl-1,2,4-triazin-5(2H)-one.

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (1), 160.pdf
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17.
Инвентарный номер: нет.
   
   P 93


    Prokhorov, A. M.
    Direct introduction of acetylene moieties into azines by S(N)H methodology [Text] / A. M. Prokhorov, M. Makosza, O. N. Chupakhin // Tetrahedron Letters. - 2009. - Vol. 50, № 13. - P1444-1446
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the corresponding ethynylazines 2a–g. Reaction with lithium acetylide requires subsequent acylation of the intermediate anionic adduct for rearomatization whereas in the case of potassium acetylide, auto-aromatization takes place??

\\\\Expert2\\nbo\\Tetrahedron Letters\\2009, V. 50, N 13, p.1444.pdf
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18.
Инвентарный номер: нет.
   
   S 10


   
    S-N(H) Reactions of ferrocenyllithium and azine N-oxides [Text] / O. N. Chupakhin, M. V. Varaksin, I. A. Utepova, V. L. Rusinov // ARKIVOC. - 2009. - Vol. 2009, № 6. - P208-220
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A non-catalytic C-C coupling of ferrocenyllithium and heterocyclic N-oxides 2 was carried out for the first time using the reaction of nucleophilic substitution of hydrogen (SNH) in azines

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19.
Инвентарный номер: нет.
   
   A 89


   
    Asymmetric induction in the nucleophilic addition in the series of aromatic azines [Electronic resource] / I. N. Egorov, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Reviews. - 2005. - Vol. 74, № 12. - P1073-1087
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Stereoselective reactions of nucleophilic addition to the C=N bond in aromatic azines resulting in chiral products are reviewed. Various methods of inducing the optical activity are discussed.

\\\\Expert2\\nbo\\Russian Chemical Reviews\\2005, V.74, p.1073.pdf
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20.
Инвентарный номер: нет.
   
   Ч-92


    Чупахин, О. Н.
    Нуклеофильная атака на незамещенный атом углерода азинов и нитроаренов - эффективная методология построения гетероциклических систем [] = Nucleophilic attack on the unsubstituted carbon atoms of azines and nitroarenes as an efficient strategy for constructing heterocyclic systems : обзор / О. Н. Чупахин, Д. Г. Береснев // Успехи химии. - 2002. - Т. 71, N 9. - 803-818: схем. - Библиогр. : с. 817-818 (69 назв.) . - ISSN 0042-1308
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Обобщены данные о новых методах синтеза конденсированных азинов с помощью нуклеофильной атаки на незамещенный атом углерода азинов и нитроаренов. Рассмотрены тандемы реакций нуклеофильного присоединения AN-AN, нуклеофильного присоединения-замещения AN-S(ipso)N, нуклеофильного замещения S(H)N-S(ipso)N и S(H)N-S(H)N, протекающих между азинами и бинуклеофилами; внутримолекулярные S(H)N-реакции в ряду азинов и нитроаренов, а также другие методы синтеза конденсированных гетероциклов, основанные на процессах нуклеофильного замещения типа S(H)N

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