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 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 |
S 10 S-N(H) approach in the synthesis of nitronyl nitroxides [Text] / O. N. Chupakhin, I. A. Utepova, M. V. Varaksin, E. V. Tretyakov, G. V. Romanenko, V. Ovcharenko, D. V. Stass // Journal of Organic Chemistry. - 2009. - Vol. 74, № 7. - P2870-2872 Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2009, v.74, p.2870.pdf |
S 81 Stable sigma(H)-adducts in reactions of ferrocenyllithium with azines [Electronic resource] / I. A. Utepova, A. E. Lakhina, M. V. Varaksin, I. S. Kovalev, V. L. Rusinov, P. A. Slepukhin, M. I. Kodess, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 10. - P2156-2161 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Stable sigma(H)-adducts as intermediates of the nucleophilic substitution of hydrogen in 3-(2-pyridyl)-1,2,4-triazines were obtained for the first time using ferrocenyllithium as a nucleophilic reagent. The three-dimensional structures of the reaction products were established based on the X-ray diffraction study of 1-[4-ethyl-6-phenyl-3-(2-pyridyl)-5(H)-1,2,4-triazin-5-yl]f \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (10), 2156.pdf |
F 42 Ferro- and antiferromagnetic interactions in polymeric and molecular complexes of Cu(hfac)2 with 1-oxoazin-2-yl-substituted nitronyl nitroxides [Text] / O. N. Chupakhin, E. V. Tretyakov, I. A. Utepova, M. V. Varaksin, G. V. Romanenko, A. S. Bogomyakov, S. L. Veber, V. Ovcharenko // Polyhedron. - 2011. - Vol. 30, № 4. - P647-653. - Bibliogr. : p. 653 (9 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Solid heterospin compounds based on Cu(hfac)2 complexes with a new group of nitronyl nitroxides bearing different azine-N-oxide substituents at position 2 of the 2-imidazoline ring (Ln) were studied. The major factor responsible for the change in the magnetic characteristics of the [Cu(hfac)2L1] complex with triazine nitronyl nitroxide with temperature was shown to be the specific pairwise packing of heterospin molecules with the dominant antiferromagnetic exchange between the radical fragments of adjacent molecules. For complexes of Cu(hfac)2 with 1-oxoazin-2-yl-substituted nitronyl nitroxides L2 and L4, 7-membered metallocycles were obtained, although they form rarely. It was shown that polymer chains formed in the solid complex with spin-labeled pyrazine-N-oxide [(Cu(hfac)2)3(L3)2] due to the cross-linking of {(Cu(hfac)2)2(L3)2} binuclear fragments via the bridging [Cu(hfac)2].???? \\\\Expert2\\nbo\\Polyhedron\\2011. v.30. p.647.pdf |
N 52 New approach to synthesis of nitronyl and imino nitroxides based on S(N)(H) methodology [Text] / E. V. Tretyakov, I. A. Utepova, M. V. Varaksin, S. E. Tolstikov, G. V. Romanenko, A. S. Bogomyakov, D. V. Stass, V. Ovcharenko, O. N. Chupakhin // ARKIVOC. - 2011. - Part 8. - P76-98 : ил. - Bibliogr. : p. 98 (36 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: It is shown that S(N)(H) approach opens new possibilities in the synthesis of polyfunctional nitronyl and imino nitroxides. It is found that the interaction of 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl lithium salt Li1 with 3,6-diaryl-1,2,4-triazines leads to formation of the corresponding triazines bearing nitronyl nitroxide or imino nitroxide substituent at position 5 of the heterocycle. The reaction of Li1 with pyridazine-N-oxide gives rise to nitroxide with buten-3-ynyl substituent 5. Spin-labeled 5 could be readily transformed by the use of 1,3-dipolar and nucleophilic addition reactions, as well as oxidative coupling, that gives a large group of new paramagnets: 2-(1H-pyrazol-5-yl)vinyl-, 2-ethynylcyclopropyl-, 2-(3-(ethoxycarbonyl) isoxazol-5-yl)vinyl-, 1-(pyrrolidin-1-yl)but-3-ynyl-substituted nitronyl nitroxide and a diradical -2,2'-((1E,7E)-octa-1,7-dien-3,5-diyne-1,8-diyl)bis(4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl). The new nitroxides were characterized by X-ray single crystal data, ESR and static magnetic susceptibility measurements |
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 |
V 29 Varaksin, M. V. Direct C-C coupling of cyclic aldonitrones with 1,2,4-triazines using SN H reactions [Электронный ресурс] / M. V. Varaksin, I. A. Utepova, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 2012. - Vol.48, №8. - P1213-1219 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,4-TRIAZINES -- ALDONITRONES -- SnH REACTIONS Аннотация: New nitrogen heterocyclic derivatives were obtained by a direct uncatalyzed by metals C-C cross-coupling of a cyclic aldonitrone lithium derivative with 1,2,4-triazines \\\\Expert2\\NBO\\Chemistry of Heterocyclic Compounds\\2012, v.48, N 8, p.1213-1219.pdf |
S 98 Synthesis of nitroxyl radical by direct nucleophilic functionalization of a C-H bond in the azadiene systems [Electronic resource] / M. V. Varaksin, E. V. Tretyakov, I. A. Utepova, G. V. Romanenko, A. S. Bogomyakov, D. V. Stass, R. S. Sagdeev, V. Ovcharenko, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2012. - Vol.61, №7. - С. 1469-1473. - Bibliogr. : p. 1473 (15 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NITRONES -- NITRONYL NITROXYLS -- ESR SPECTRA Аннотация: Cyclic dinitrones underwent nucleophilic substitution of the hydrogen atom in the reaction with a paramagnetic carbanion, the lithium derivative of 4,4,5,5 tetramethyl 4,5 dihydro 1H imidazol 1 oxyl 3 oxide, to give polyfunctional nitronyl nitroxyls \\\\expert2\\NBO\\Russian Chemical Bulletin\\2012, 61 (7), 1469-1473.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 |
S 10 S-N(H) Approach in the Synthesis of meso-Substituted Heterocyclic Calix[4]arenes / K. A. Khlamkin, 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. 236. - Bibliogr. : p. 236 (4 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HETEROCYCLES -- HETEROCYCLIC COMPOUNDS -- CALIXARENES |
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 |
D 62 Direct C(sp2)-H Bond Functionalization in Cyclic Aldonitrones: Palladium(II)-Catalyzed Oxidative Cross-Coupling and Eliminative SNH Reactions / M. V. Varaksin, O. N. Chupakhin, V. N. Charushin, S. V. Mikhaylov, I. A. Utepova, B. A. Trofimov // 18th European Symposium on Organic Chemistry ESOC-2013, Marseille, France, 7-12 July 2013 : book of abstracts. - Marseille, France, 2013. - С. 329 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PALLADIUM(II) -- SNH REACTIONS -- CYCLIC ALDONITRONES |
H 62 Heterocyclic and Open-Chain Carboranes via Transition-Metal-Free C-H Functionalization of Mono- and Diazine-N-oxides [Electronic resource] / L. A. Galliamova, M. V. Varaksin, O. N. Chupakhin, P. A. Slepukhin, V. N. Charushin // Organometallics. - 2015. - Vol. 34, № 21. - С. 5285-5290. - Bibliogr. : p. 5290 (27 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CYCLOMETALATED IRIDIUM COMPLEXES -- NEUTRON-CAPTURE THERAPY -- PHARMACOPHORES Аннотация: For the first time, the direct C(sp(2))-H functionalization methodology has successfully been applied to cause nucleophilic modification of mono- and diazine-N-oxides with the 1,2-closo-carborane moiety. As a result of these cross-coupling reactions uncatalyzed by transition metals, a series of novel C-modified heterocyclic and open-chain (vinyl acetylene) carboranes have been obtained. Complexes of phenanthrolinyl-substituted omicron-carborane with Cu(II) of various architectures have been synthesized. \\\\expert2\\nbo\\Organometallics\\2015. V. 34, N 21. P. 5285.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 |
Methodology of C(sp2)-H functionalization in mono- and diazine N-oxides in the synthesis of heterocyclic meso-substituted calixarenes [Electronic resource] / M. V. Varaksin, O. N. Chupakhin, V. N. Charushin, K. A. Khlamkin, I. A. Utepova // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2015. - Vol. 6, № 5. - С. 1093-1096 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): MESO-SUBSTITUTED CALIXARENES -- MESO-SUBSTITUTED AZINYLCALIXARENES -- METAL CATALYSIS Аннотация: Earlier unknown meso-substituted azinylcalixarenes were obtained by a direct cross-coupling of 2-lithium-25,26,27,28-tetramethoxycalix[4]arenes with mono- and diazine N-oxides without transition metal catalysis. \\\\expert2\\nbo\\Russian Chemical Bulletin\\2015, 64 (5), 1093-1096.pdf |
D 62 Direct CC coupling of phthalazine-N-oxide with the carboranyl anion - An original approach to C-modification of carboranes / M. V. Varaksin, L. A. Galliamova, O. A. Stepanova, O. S. Eltsov, O. N. Chupakhin, V. N. Charushin // Journal of Organometallic Chemistry. - 2017. - Vol. 830. - P93-99 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CARBORANES -- C-C COUPLING -- PHTHALAZINE-N-OXIDE Аннотация: An original transition metal-free approach based on the direct CC coupling of phtalazine-N-oxide with the carboranyl anion has been developed. A series of the novel C-modified closo-carboranes such as 1-(2-oxido-3-acyl-3,4-dihydrophtalazinyl-4-yl)-1,2-dicarba-closo-dodecaboranes and 1-(2-formylbenzyl)-1,2-dicarba-closo-dodecaborane have been obtained. The synthesized boron clusters could be of interest as promising building blocks in design of BNCT delivery agents. |
D 62 Direct c[sbnd]c coupling of phthalazine-n-oxide with the carboranyl anion – an original approach to c-modification of carboranes / M. V. Varaksin, L. A. Galliamova, O. A. Stepanova, O. S. Eltsov, O. N. Chupakhin, V. N. Charushin // Journal of Organometallic Chemistry. - 2017. - Vol. 830. - P93-99 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CARBORANES -- C[SBND]C COUPLING -- PHTHALAZINE-N-OXIDE Аннотация: An original transition metal-free approach based on the direct C[sbnd]C coupling of phtalazine-N-oxide with the carboranyl anion has been developed. A series of the novel C-modified closo-carboranes such as 1-(2-oxido-3-acyl-3,4-dihydrophtalazinyl-4-yl)-1,2-dicarba-closo-dodecaboranes and 1-(2-formylbenzyl)-1,2-dicarba-closo-dodecaborane have been obtained. The synthesized boron clusters could be of interest as promising building blocks in design of BNCT delivery agents. |
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. |
V 29 Varaksin, M. V. Strategy of direct C(SP2)-H functionalization in non-aromatic azaheterocycles as an efficient approach towards novel 2H-imidazole derivatives / M. V. Varaksin, A. A. Akulov, T. D. Moseev, O. N. Chupakhin, V. N. Charushin // Современные синтетические методологии для создания лекарственных препаратов и функциональных материалов (MOSM2018): вторая международная научно-практическая конференция : материалы и доклады. - Екатеринбург, 2019. - С. 139-140 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
S 68 Smyshliaeva, L. A. C-H functionalization methodology in the synthesis of novel azaheterocyclic carboranes / L. A. Smyshliaeva, M. V. Varaksin, V. N. Charushin, O. N. Chupakhin // Современные синтетические методологии для создания лекарственных препаратов и функциональных материалов (MOSM2018): вторая международная научно-практическая конференция : материалы и доклады. - Екатеринбург, 2019. - С. 206 Рубрики: ХИМИЧЕСКИЕ НАУКИ |