C 47 Charushin, V. N. Nucleophilic aromatic substitution of hydrogen and related reactions [Electronic resource] / V. N. Charushin, O. N. Chupakhin // Mendeleev Communications. - 2007. - Vol. 17, № 5. - P249-254 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The classical concept of nucleophilic aromatic substitution (SNAripso) has been complemented with a new synthetic methodology (SNH), enabling one to build new carbon–carbon C(sp2)–C(sp3), C(sp2)–C(sp2) and C(sp2)–C(sp) or carbon–heteroatom C(sp2)–X (X is O, N, P, S, halogen) bonds through nucleophilic displacement of hydrogen in an aromatic ring. \\\\Expert2\\nbo\\Mendeleev Communications\\2007, v.17, p.249.pdf |
I-69 Intramolecular nucleophilic substitution of hydrogen in (quinoxalinyl-2)aminovinyl derivatives as a new approach to pyrrolo- and indolo[2,3-beta]quinoxalines [Text] / S. K. Kotovskaya, V. N. Charushin, N. M. Perova, M. I. Kodess, O. N. Chupakhin // Synthetic Communications. - 2004. - Vol. 34, № 14. - P2531-2537 : ил. - Библиогр.: с. 2537 (10 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NUCLEOPHILIC SUBSTITUTION -- HYDROGEN -- KETONE Аннотация: Pyrrolo[2,3-beta]- and indolo[2,3-e]quinoxalines were obtained by the reaction of 2-aminoquinoxalines with ketones followed by the intramolecular displacement of hydrogen at C-3 in (quinoxalinyl-2)aminovinyl derivatives. |
F 70 Fluoro-containing Heterocycles: VI. New Derivatives of 1,3,4-Thiadiazino[6,5,4-i,j]quinoline [Electronic resource] / E. V. Nosova, G. N. Lipunova, L. P. Sidorova, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2001. - Vol. 37, № 8. - P1169-1176 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A series of new tricyclic fluoroquinolones was prepared by replacing fluorine atoms in derivatives of 2-R-8-Y-7-oxo-9,10-difluoro-7H-1,3,4-thiadiazino[6,5,4-i,j]quinoline-6-carboxylic acids. In acids and esters containing a hydrogen atom in position 8 occurred replacement of F10 by amine rests, and in compounds with a fluorine in position 8 was substituted either F8or F10 and F8depending on the amine character \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (8), 1169.pdf |
T 19 Tandem of nucleophilic substitution of hydrogen and cyclocondensation with participation of nitro group in the synthesis of fluorine-containing 3-amino-1,2,4-benzotriazines [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). - 2006. - Vol. 55, № 7. - P1243-1247 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 3-fluoro-1-nitrobenzenes with guanidine hydrochloride in THF in the presence of ButOK gave isomeric 5-and 7-fluoro-containing 3-amino-1,2,4-benzotriazines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2006, 55 (7), 1243.pdf |
S 98 Synthesis of fluorine-containing quinoline-2,3-dicarboxylates from products of vicarious nucleophilic substitution of hydrogen in 3-fluoronitroarenes [Electronic resource] / S. K. Kotovskaya, G. A. Zhumabaeva, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 1. - P170-175 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 3-fluoro-4-R-6-phenylsulfonylmethylnitrobenzenes with dimethyl fumarate or diethyl maleate in acetonitrile in the presence of an excess of K2CO3 and a catalytic amount of 18-crown-6 afforded mixtures of dialkyl 6-R-7-fluoro- and dialkyl 6-R-7-phenylsulfonylquinoline-2,3-carboxylate N-oxides, as well as dialkyl 6-R-7-fiuoro- quinoline-2,3-carboxylates (alkyl is methyl or ethyl), which were resolved by column chromatography and identified by 1H NMR spectroscopy and X-ray diffraction \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (1), 170-175.pdf |
C 45 Changes in the vibrational characteristics of substituted 1,2,4,5-tetrazines after complexation with 1,2,3-benzotriazole: A theoretical study [Electronic resource] / N. N. Ivshina, E. V. Bartashevich, V. A. Potemkin, M. A. Grishina, R. I. Ishmetova, G. L. Rusinov, N. I. Latosh, P. A. Slepukhin, V. N. Charushin // Journal of Structural Chemistry. - 2009. - Vol. 50, № 6. - P1053-1058 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The complexation of 3,6-substituted 1,2,4,5-tetrazines with benzotriazole was studied theoretically based on the vibrational spectra. For model complexes, the energy was minimized by the geometrical parameters, and the spectral characteristics were calculated by the PM3 method. The shift of the bond vibration frequencies of the atoms involved in complexation after the formation of different various intermolecular contacts was determined. This made it possible to determine the type of intermolecular interaction and suggest the structures of the complexes \\\\Expert2\\nbo\\Journal of Structural Chemistry\\2009, V. 50, N 6, p.1053.pdf |
C 57 Chupakhin, O. N. Nucleophilic aromatic substitution of hydrogen [Text] : научное издание / O. N. Chupakhin, V. N. Charushin, Henk C. van der Plas. - [S. l.] : Academic Press, 1994. - 376p. - Б. ц. Рубрики: ХИМИЧЕСКИЕ НАУКИ |
S 98 Synthesis of chelating polymer sorbents by using the S-N(H) methodology / A. V. Pestov, P. A. Slepukhin, Yu. G. Yatluk, V. N. Charushin, O. N. Chupakhin // Journal of Applied Polymer Science . - 2012. - Vol.125, №3. - С. 1970-1978 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): FUNCTIONALIZATION OF POLYMERS -- PHENOL -- X-RAY ANALYSIS Аннотация: The article describes a new synthetic approach to modify the structure of phenol-formaldehyde and resorcinol-formaldehyde resins, which enables one to functionalize a polymer matrix by using the S?NH (nucleophilic aromatic substitution of hydrogen) methodology. Direct heteroarylation of phenol (resorcinol) fragments in polymer chains with 1,2,4-triazine derivatives illustrates a new synthetic method in the polymer chemistry. The feature of this methodology is that it provides an opportunity to accomplish direct one-pot polymer transformations by incorporating of rather complicated chelating groups through the displacement of hydrogen in phenol moieties. It has been shown that in order to obtain chemically modified polymers on the basis of phenol-formaldehyde and resorcinol-formaldehyde resins with a high degree of substitution with chelating units, a polymer matrix has to react with 3-(pyridin-2'-yl)-1,2,4-triazin-5(2H)-one. Also, it has been found that polymer sorbents with a high selectivity can be obtained by using the template method. Targeted synthesis of model compounds, as structural units of the chelating polymers, and elucidation of the structure of their complexes with copper (II) ions have shown that the most plausible type of coordination is formation of the bridge 1 : 1 complexes of the a,a'-bipyridinyl type. \\\\expert2\\nbo\\Journal of Applied Polymer Science\\2012, vol.125,p.1970.pdf |
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 |
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 |
P 17 Palladium(II)-Catalyzed Oxidative C–H/C–H Coupling and Eliminative SNH Reactions in Direct Functionalization of Imidazole Oxides with Indoles / M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Journal of Organic Chemistry. - 2012. - Vol.77, №20. - С. 9087-9093 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): IMIDAZOLE OXIDES -- INDOLES Аннотация: Two novel synthetic approaches to realize the direct C(sp2)–H bond functionalization in cyclic nitrones are reported. Palladium(II)-catalyzed oxidative C–C coupling of 2,2-dialkyl-4-phenyl-2H-imidazole 1-oxides with indoles was shown to result in the formation of 5-indolyl-3-yl derivatives, while nucleophilic substitution of hydrogen (SNH) at C(5) of the same imidazole system was found to afford the corresponding deoxygenated compounds \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2010, v.77, p.9087.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 |
S 98 Synthesis, spectral and electrochemical properties of pyrimidine-containing dyes as photosensitizers for dye-sensitized solar cells [Electronic resource] / E. V. Verbitskiy [и др.] // Dyes and Pigments. - 2014. - Vol.100. - С. 201-214. - Bibliogr. : p. 213-214 (37 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ORGANIC DYES -- PYRIMIDINE -- MICROWAVE-ASSISTED Аннотация: Six novel donor–π–acceptor organic dyes bearing a pyrimidine as the anchoring group have been obtained in good yields by combination of the microwave-assisted Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen reactions. Their absorption, photoluminescence and electrochemical properties were fully investigated in detail. The infrared spectra of dyes adsorbed on TiO2 indicate the formation of coordinate bonds between the pyrimidine ring of dyes and the Lewis acid sites (exposed Tin+ cations) of the TiO2 surface. This work demonstrates that the pyrimidine rings of dye sensitizers that form a coordinate bond with the Lewis acid site of a TiO2 surface are promising candidates as the electron-withdrawing anchoring group. The data from quantum calculations show that all of the dyes are potentially good photosensitizers for dye-sensitized solar cells \\\\expert2\\NBO\\Dyes and Pigments\\2014, v. 100, p.201-214.pdf |
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 |
D 62 Direct nucleophilic functionalization of C(sp2)–H-bonds in arenes and hetarenes by electrochemical methods [Electronic resource] / A. V. Shchepochkin, O. N. Chupakhin, V. N. Charushin, V. A. Petrosyan // Russian Chemical Reviews. - 2013. - Vol.82, №8. - С. 747-772. - Bibliogr. : p. 770-772 (133 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NUCLEOPHILIC FUNCTIONALIZATION -- C(sp2)–H-BONDS -- HETARENES Аннотация: The data on the main electrochemical methods and approaches used for the direct functionalization of the C(sp2)–H-bond proceeding via the mechanisms of nucleophilic substitution of hydrogen (SNH-reaction) are classified and summarized. The important features of preparative electrochemical processes are considered. A special emphasis is placed on the synthetic potential of the discussed transformations \\\\expert2\\NBO\\Russian Chemical Reviews\\2013, V.82, N8, p.747.pdf |
B 62 Bis(1,1,1,3,5,5,5-heptafluoro-4-iminopent-2-ene-2-aminato)copper(ii) — a new metal-containing matrix in the design of heterospin systems [Electronic resource] / S. V. Fokin, V. Ovcharenko, G. V. Romanenko, E. V. Tretyakov, A. S. Bogomyakov, V. I. Saloutin, T. I. Filyakova, L. V. Saloutina, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 816-823. - Bibliogr. : p. 823 (11 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): COPPER(II) -- BISCHELATES -- NITROXIDES Аннотация: The first heterospin compounds based on bis(1,1,1,3,5,5,5 heptafluoro 4 iminopent 2 ene 2 aminato)copper(II) (CuL2) and nitronyl nitroxide radicals, 2 R 4,4,5,5 tetramethyl 4,5 dihydro 1H imidazole 3 oxide 1 oxyls (NIT R, where R = H, Me, Ph, and 1 methyl pyrazol 4 yl), were synthesized and structurally characterized. An important peculiarity of the structure of synthesized solid phases is the formation of a supramolecular structure due to hydrogen bonds between the oxygen atoms of the nitronyl nitroxide fragments of NIT R and the hydrogen atoms of the NH groups of CuL2 \\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (5), 816-823.pdf |
S 98 Synthesis of 4-(thien-2-yl)-substituted coumarins through Lewis acid catalyzed Michael addition of thiophenes to 3-benzoylcoumarins followed by oxidation [Electronic resource] / R. A. Irgashev, A. A. Karmatsky, G. L. Rusinov, V. N. Charushin // Tetrahedron Letters. - 2014. - Vol.55, №26. - С. 3603-3606 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): THIOPHENES -- 3-BENZOYLCOUMARINS -- Lewis acid Аннотация: 3-Benzoyl-4-(thien-2-yl)coumarins have been obtained in good yields according to the SNH addition–oxidation protocol, involving the diastereoselective addition of thiophenes at C-4 of 3-benzoylcoumarins under BBr3 catalysis, followed by oxidation of the intermediate 3,4-trans-3-benzoyl-4-(thien-2-yl)-3,4-dihydrocoumarins with DDQ. This two-step procedure can be regarded as nucleophilic substitution of hydrogen (SNH) on the heterocyclic ring of coumarins \\\\expert2\\nbo\\Tetrahedron Letters\\2014, v. 55, p. 3603.pdf |
S 98 Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions [Electronic resource] / M. A. Kravchenko, E. V. Verbitskiy, I. D. Medvinskiy, G. L. Rusinov, V. N. Charushin // Bioorganic and Medicinal Chemistry Letters. - 2014. - Vol. 24, №14. - С. 3118-3120 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINE -- ANTIMICOBACTERIAL -- TUBERCULOSIS Аннотация: Combination of the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (SNH) reactions proved to be a convenient method for the synthesis of 5-styryl-4-(hetero)aryl substituted pyrimidines from commercially available 5-bromopyrimidine. All intermediate 5-bromo-4-(hetero)aryl substituted pyrimidines and also the targeted 5-styryl-4-(hetero)arylpyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H37Rv, avium, terrae, and multi-drug-resistant strain isolated from tuberculosis patients in Ural region (Russia). It has been found that some of these compounds possess a low toxicity and have a bacteriostatic effect, comparable and even higher with that of first-line antituberculosis drugs \\\\expert2\\nbo\\Bioorganic and Medicinal Chemistry Letters\\2014, v. 24, p. 3118.pdf |
S 90 Study of the supramolecular structures of complexes of carborane-containing pyridazines with 2,3,5,6-tetrachloro-1,4-dihydroxybenzene [Electronic resource] / P. A. Slepukhin, S. G. Tolshchina, A. V. Ignatenko, E. F. Zhilina, V. N. Charushin // Crystallography Reports. - 2014. - Vol.59, №2. - С. 202-206. - Bibliogr. : p. 206 (9 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIDAZINES -- HETEROCYCLIC SUBSTITUENTS -- CARBORANE MOIETY Аннотация: The structures and characteristic features of the molecular packing patterns of complexes of pyridazines containing heterocyclic substituents and the carborane moiety with 2,3,5,6-tetrachlorohydroquinone (TCHQ) were investigated. It was shown that TCHQ can form supramolecular assemblies with carborane-containing substituted pyridazines. The stoichiometry and three-dimensional structures of these assemblies depend on the substituents in the pyridazine ring and are formed via O-H⋯N hydrogen bonding between TCHQ and heterocyclic molecules \\\\expert2\\NBO\\Crystallography Reports (Кристаллография)\\2014, v.59, N 2, p.202-206.pdf |
C 47 Charushin, V. N. Metal Free C-H Functionalization of Aromatics. Nucleophilic Displacement of Hydrogen / V. N. Charushin, O. N. Chupakhin. - [Б. м.] : Springer International Publishing Switzerland, 2014. - 283 с. - ISBN 1861-9282 : Б. ц. Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AROMATIC COMPOUNDS -- AROMATIC NUCLEOPHILES |