A 53 An unusual aromatisation of dihydropyrimidines facilitated by reduction of the nitro group [Electronic resource] / G. L. Rusinov, E. B. Gorbunov, V. N. Charushin, O. N. Chupakhin // Tetrahedron Letters. - 2007. - Vol. 48, № 33. - P5873-5876 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: An unusual aromatisation of the dihydropyrimidine fragment in 6-nitro-7-substituted-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines has first been found to occur in parallel with reduction of the nitro group using a number of reducing agents. \\\\Expert2\\nbo\\Tetrahedron Letters\\2007, v. 48, p.5873.pdf |
Y 12 Yachevskii, D. S. Synthesis of regioisomeric polyfluoroalkylpyrazolo[1,5-a]pyrimidines [Electronic resource] / D. S. Yachevskii, D. L. Chizhov, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 1. - P142-144. - Библиогр. : с. 144 (3 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The article discusses a study that illustrates the synthesis of regioisometric polyfluoroalkylpyrazolo[1,5-a]pyramidines in 2 schemes. Polyfluoroalkyl-containing 1,3,5-triketones are convenient and promising reagents for building up various heterocyclic systems. Reactions of triketones as well as their dehydration products are examined. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (1), 142.pdf |
F 70 Fluoro-containing Heterocycles: V. Cyclization of 3-Azolylamino-2-polyfluorobenzoylacrylates [Electronic resource] / G. N. Lipunova, E. V. Nosova, M. I. Kodess, V. N. Charushin, Yu. A. Rozin, O. M. Chasovskikh // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2001. - Vol. 37, № 4. - P570-576 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The heating of ethyl 3-azolylamino-2-polyfluorobenzoylacrylates in acetonitrile in the presence of KF gave rise to derivatives of 1-azolyl-substituted quinolones or azolo[1,5-a]pyrimidines?? \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (4), 570.pdf |
O-57 One-pot synthesis of 6H-pyrrolo[2,3-e[1,2,4]triazolo[1,5-a]pyrimidines on the basis of delta H-adducts of 6-Nitro[1,2,4]triazolo[1,5-a]pyrimidine with carbonyl compounds [Electronic resource] / E. B. Gorbunov, G. L. Rusinov, R. I. Ishmetova, V. N. Charushin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2008. - Vol. 44, № 1. - P128-132 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Aromatic, heteroaromatic, and aliphatic carbonyl compounds reacted with 6-nitro[1,2,4]triazolo[1,5-a]pyrimidine in the presence of a base to give stable ?H-adducts at C7. Reduction of the nitro group in the latter is accompanied by tandem autoaromatization of the azine ring and intramolecular cyclocondensation with formation of the corresponding 6H-pyrrolo[2,3-e][1,2,4]triazolo[1,5-a]pyrimidines \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2008, 44 (1), 128.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 |
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 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 91 Substituted pyrimidines: synthesis, photophysical properties and biological activity / E. M. Cherprakova, E. V. Verbitskiy, M. A. Kravchenko, I. D. Medvinskiy, G. L. Rusinov, 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. 77 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINES -- SYNTHESIS -- PHOTOPHYSICAL PROPERTIES -- BIOLOGICAL ACTIVITY |
C 75 Consecutive SNH and Pd-catalyzed coupling reactions – an efficient synthetic strategy to pyrimidines bearing electron-rich heterocyclic fragments / V. N. Charushin, O. N. Chupakhin, G. L. Rusinov, E. V. Verbitskiy, E. M. Cherprakova // 18th European Symposium on Organic Chemistry ESOC-2013, Marseille, France, 7-12 July 2013 : book of abstracts. - 2013. - 158 (P1-089) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- Pd-CATALYZED -- HETEROCYCLIC FRAGMENTS |
D 64 Dithienoquinazolines – A Convenient Synthesis by the Oxidative Photocyclization of 4,5-Dithienyl-Substituted Pyrimidines and Their Photophysical Properties [Electronic resource] / E. V. Verbitskiy, P. A. Slepukhin, M. S. Valova, E. M. Cherprakova, A. V. Schepochkin, G. L. Rusinov, V. N. Charushin // European Journal of Organic Chemistry. - 2014. - № 36. - С. 8133-8141 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DITHIENOQUINAZOLINES -- PYRIMIDINES -- PHOTOPHYSICAl PROPERTIES Аннотация: A convenient route to a new class of thienoacene systems bearing a fused pyrimidine ring is presented along with their optoelectronic properties. The photophysical and electrochemical properties of these newly developed thieno-aza-acenes have been investigated by UV/Vis absorption and photoluminescence spectrophotometry and cyclic voltammetry, and some crystal structures have also been determined. \\\\expert2\\nbo\\European Journal of Organic Chemistry\\2014, № 36. p.8133-8141.pdf |
S 98 Synthesis and characterization of new complexes derived from 4-thienyl substituted pyrimidines [Electronic resource] / E. M. Cherprakova, E. V. Verbitskiy, M. A. Kiskin, G. G. Aleksandrov, P. A. Slepukhin, A. A. Sidorov, D. V. Starichenko, Yu. N. Shvachko, I. L. Eremenko, G. L. Rusinov, V. N. Charushin // Polyhedron. - 2015. - Vol. 100. - С. 89-99. - Bibliogr. : p. 98-99 (42 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINE -- CYCLOPALLADATION -- MAGNETIC-PROPERTIES Аннотация: The behavior of 4-thienyl substituted pyrimidine ligands (L1-3) has been studied for the series of their reactions with various salts of 3d metals (Co, Zn, Ni, Cu) and platinoids (Pt, Pd). In particular, mononuclear Co(OTf)(2)(L1-3)(2)(H2O)(2)(MeCN)(2) (1), binuclear Co-2(Piv)(2)(L1-3)(4) (2a,b), Cu-2(Piv)(2)(L1-3)(2) (5a,b), heterometallic polynuclear Li2Co2(Piv)(6)(L1-3)(2) (4) and chelate [(L-1)Pd(OAc)](2) (6) complexes have been obtained. The structures of all complexes have been established by X-ray diffraction. Also magnetic properties of coordination compounds 1, 2, 4 and 5 have been studied in details. In particular, mononuclear Co(II) complexes I and 4 proved to exhibit paramagnetism with large positive zero-field splitting parameters. Dinuclear Co(II) complexes 2a,b show weak antiferromagnetic interactions. Dinuclear Cu(II) complexes 5a,b demonstrate strong antiferromagnetic superexchange interactions via four carboxylate bridges. The systems 2a,b and 5a,b are isolated as exchange coupled dimers \\\\expert2\\nbo\\Polyhedron\\2015, v.100, p.89-99.pdf |
S 98 Synthesis, and structure-activity relationship for C(4) and/or C(5) thienyl substituted pyrimidines, as a new family of antimycobacterial compounds [Electronic resource] / E. V. Verbitskiy, E. M. Cherprakova, P. A. Slepukhin, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // European Journal of Medicinal Chemisrty. - 2015. - Vol. 96. - С. 225-234. - Bibliogr. : p. 234 (36 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\expert2\\nbo\\European Journal of Medicinal Chemistry\\2015, v.96, p.225-234.pdf |
S 98 Synthesis of 2H-azolo[1,5-a][1,2,3]triazolo[4,5-e]pyrimidines [Electronic resource] / E. B. Gorbunov, G. L. Rusinov, E. N. Ulomskii, M. L. Isenov, V. N. Charushin // Chemistry of Heterocyclic Compounds. - 2015. - Vol. 51, № 5. - С. 491-495. - Bibliogr. : p. 494-495 (27 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2015, v.51, N 5, p. 491-495.pdf |
S 98 Synthesis, Photophysical and Redox Properties of the D-pi-A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety [Electronic resource] / E. V. Verbitskiy [и др.] // Journal of Fluorescence. - 2015. - Vol. 25, № 3. - С. 763-775. - Bibliogr. : p. 774-775 (51 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINES -- CARBAZOLE -- DYE-SENSITIZED SOLAR CELLS Аннотация: Novel donor-pi-acceptor dyes bearing the pyrimidine unit as an electron-withdrawing group have been synthesized by using combination of two processes, based on the microwave-assisted Suzuki cross-coupling reaction and nucleophilic aromatic substitution of hydrogen. Spectral properties of the obtained dyes in six aprotic solvents of various polarities have been studied by ultraviolet-visible and fluorescence spectroscopy. In contrast to the absorption spectra, fluorescence emission spectra displayed a strong dependence from their solvent polarities. The nature of the observed long wavelength maxima has been elucidated by means of quantum chemical calculations. The electrochemical properties of these dyes have been investigated by using cyclic voltammetry, while their photovoltaic performance was evaluated by a device fabrication study. The experimental and calculation data show that all of the dyes can be regarded as potentially good photosensitizers for dye-sensitized solar cells. \\\\expert2\\nbo\\Journal of Fluorescence\\2015, v.25, p.763-775.pdf |
S 98 Synthesis of 6-thienyl-substituted 2-amino-3-cyanopyridines [Electronic resource] / E. V. Verbitskiy, E. M. Cheprakova, M. G. Pervova, G. G. Danagulyan, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2015. - С. 689-694. - Bibliogr. : p. 694 (25 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINES -- TRANSFORMATIONS OF HETEROCYCLE -- PYRIDINES Аннотация: An efficient method for the synthesis of 6-thienyl-substituted 2-amino-3-cyanopyridines by the ring transformation in the corresponding pyrimidines was developed. Further modification of the pyridines obtained under conditions of a room temperature aerobic Suzuki reaction in the presence of trans-bis(dicyclohexylamine) palladium(II) acetate as a catalyst was studied. \\\\expert2\\nbo\\Russian Chemical Bulletin\\2015, 64 (3), 689-694.pdf |
S 98 Synthesis of new C(4) and/or C(5) thienyl substituted pyrimidines as potential antimycobacterial agents. / E. V. Verbitskiy, E. M. Cheprakova, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // 19h European Symposium on Organic Chemistry (ESOC-2015), 12th-16th July, Lisboa, Portugal, 2015. : book of abstr. . - Lisboa, 2015. - С. 450 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINES -- ANTIMYCOBACTERIAL AGENTS -- SYNTHESIS |
D 47 Detection of nitroaromatic explosives by new D-π-A sensing fluorophores on the basis of the pyrimidine scaffold [Electronic resource] / E. V. Verbitskiy, A. A. Baranova, K. I. Ludovik, M. Z. Shafikov, K. O. Khokhlov, E. M. Cheprakova, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Analytical and Bioanalytical Chemistry. - 2016. - Ahead of Print Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NITROAROMATIC EXPLOSIVES -- PYRIMIDINE SCAFFOLD Аннотация: A series of D-π-A- type dyes based on pyrimidines, bearing various thiophene linkers, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that the emission of all derivs. is sensitive to the presence of nitroarom. explosives, such as 2,4,6-trinitrophenol (PA), 2,4,6-trinitrotoluene (TNT), and 2,4-dinitrotoluene (DNT), in their acetonitrile solns. The detection limits of fluorophores to PA, TNT, and DNT proved to be in the range from 5.83 × 10-6 to 2.38 × 10-7 mol/L, 1.70 × 10-4 to 8.40 × 10-6 mol/L, and 8.39 × 10-5 to 6.87 × 10-6 mol/L, resp. The theor. investigation into the quenching mechanism in the presence of fluorophore has been performed. All compds. have shown a good efficiency as sensor materials when tested as elements of the original device < \\\\expert2\\nbo\\Analytical and Bioanalytical Chemistry\\2016, Ahead Print.pdf |
S 98 Synthesis and evaluation of antitubercular activity of fluorinated 5-aryl-4-(hetero)aryl substituted pyrimidines [Электронный ресурс] / E. V. Verbitskiy, S. A. Baskakova, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Bioorganic and Medicinal Chemistry. - 2016. - Vol. 24, № 16. - С. 3771-3780 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINE -- ANTIMYCOBACTERIAL ACTIVITY -- TUBERCULOSIS Аннотация: Various 5-(fluoroaryl)-4-(hetero)aryl substituted pyrimidines have been synthesized based on the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (S-N(H)) reactions starting from commercially available 5-bromopyrimidine and their antitubercular activity against Mycobacterium tuberculosis H(37)Rv has been explored. The outcome of the study disclose that, some of the compounds have showed promising activity in micromolar concentration against Mycobacterium tuberculosis H(37)Rv, Mycobacterium avium, Mycobacterium terrae, and multidrug-resistant strains isolated from tuberculosis patients in Ural region (Russia). The data concerning the 'structure-activity' relationship for fluorinated compounds have been discussed \\\\expert2\\NBO\\Bioorganic and Medicinal Chemistry\\2016, V.24, N 16, p.3771-3780.pdf |
D 62 Direct Modification of Quercetin by 6-Nitroazolo[1,5-a]Pyrimidines [Electronic resource] / E. B. Gorbunov, G. L. Rusinov, E. N. Ulomskii, O. S. Eltsov, V. L. Rusinov, V. G. Kartsev, V. N. Charushin, I. A. Khalymbadzha, O. N. Chupakhin // Chemistry of Natural Compounds. - 2016. - Vol. 52, № 4. - С. 708-710 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DERIVATIVES -- INHIBITORS -- ANALOGS |