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 |
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 \\\\expert2\\NBO\\Macroheterocycles\\2013.6.4.308-314.pdf |
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 |
Aryne-mediated transformations of 5-perfluorophenyl-substituted 3-(pyridin-2-yl)-1,2,4-triazines in the design of novel 10-(1h-1,2,3-triazol-1-yl)pyrido[1,2-a]indole fluorophores / T. D. Moseev, M. V. Varaksin, I. A. Lavrinchenko [и др.] // Tetrahedron. - 2020. - Vol. 76, № 18. - P131147 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,3-TRIAZOLES -- ARYNE-MEDIATED TRANSFORMATIONS -- CAOSAMBHWGMFEW-UHFFFAOYSA-N -- CYFQLMLVDSTHGC-UHFFFAOYSA-N -- FLUOROARENES Аннотация: A number of novel fluorinated derivatives of the family of pyrido[1,2-a]indole fluorophores have first been synthesized via the aryne-mediated domino transformations of 5-(perfluorophenyl)-3-(pyridin-2-yl)-1,2,4-triazines. A comprehensive study of photophysical properties of the obtained polyfluoroaryl substituted derivatives, in which polyfluoroaryl, 1,2,3-triazole, and pyridoindole subunits contribute to a joint chromophore system, has shown that these compounds proved to exhibit a fluoresce with green light in acetonitrile solutions. |
Single-crystal x-ray diffraction studies in a series of 5-pentafluorophenyl-2,2'-bipyridines and their fused analogs / M. V. Varaksin, E. S. Starnovskaya, D. S. Kopchuk [и др.] // Russian journal of general chemistry. - 2020. - Т. 90, № 2. - P235-237 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 6-ARYL-5-PENTAflUOROPHENYL-2,2'-BIPYRIDINES -- LIGANDS -- SINGLE-CRYSTAL X-RAY DIFFRACTION ANALYSIS -- STRUCTURAL EFFECT Аннотация: Structure of three 6-aryl-5-pentafluorophenyl-2,2'-bipyridines has been studied by means of single-crystal X-ray diffraction analysis. The effect of some functional fragments on the structural organization of compounds, in particular, donor and acceptor substituents in the aryl moiety, as well as annulated benzene and cyclopentane rings on the molecular structure and crystal packing of pentafluorophenyl-modified 2,2'-bipyridine ligand systems has been analyzed. |
Azaheterocyclic derivatives of ortho - carborane: synthetic strategies and application opportunities / L. A. Smyshliaeva, M. V. Varaksin, V. N. Charushin, O. N. Chupakhin // Synthesis. - 2020. - Vol. 52, № 3. - P337-352 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZAHETEROCYCLES -- CARBORANES -- CARBORYNE -- CROSS-COUPLING REACTIONS -- DECABORANE Аннотация: Azaheterocyclic derivatives of 1,2-dicarba- closo -dodeca borane (ortho -carborane) are known to be of particular interest due to numerous plausible applications, particularly, in medicine, materials science, and advanced technologies. Three principal synthetic strategies resulting in azaheterocyclic carboranes, in which boron-enriched and azaheterocyclic fragments are linked to each other, either directly by means of the C-C bonds or through a short spacer (CH 2, CH 2 S, CH 2 O, etc.), have been outlined. These synthetic approaches are of general character and can be used both individually and in combination to afford promising organoboron clusters of diverse architectures. 1 Introduction 2 C-C Cross-Coupling Strategies in the Synthesis of Azahetero cyclic Carboranes 3 Carboryne-Based Transformation Strategies 4 Condensation Strategies: Reactions of Decaborane B 10 H 14 with Substituted Acetylenes 5 Conclusion and Outlook. |
Azaheterocyclic derivatives of ortho -carborane: synthetic strategies and application opportunities / L. A. Smyshliaeva, M. V. Varaksin, V. N. Charushin, O. N. Chupakhin // Synthesis. - 2020. - Т. 52, № 3. - P337-352 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CARBORANES -- AZAHETEROCYCLES -- DECABORANE -- CROSS-COUPLING REACTIONS -- CARBORYNE Аннотация: Azaheterocyclic derivatives of 1,2-dicarba- closo -dodeca borane (ortho -carborane) are known to be of particular interest due to numerous plausible applications, particularly, in medicine, materials science, and advanced technologies. Three principal synthetic strategies resulting in azaheterocyclic carboranes, in which boron-enriched and azaheterocyclic fragments are linked to each other, either directly by means of the C-C bonds or through a short spacer (CH 2, CH 2 S, CH 2 O, etc.), have been outlined. These synthetic approaches are of general character and can be used both individually and in combination to afford promising organoboron clusters of diverse architectures. 1 Introduction 2 C-C Cross-Coupling Strategies in the Synthesis of Azahetero cyclic Carboranes 3 Carboryne-Based Transformation Strategies 4 Condensation Strategies: Reactions of Decaborane B 10 H 14 with Substituted Acetylenes 5 Conclusion and Outlook. |
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 |
Aryne-mediated transformations of 5-perfluorophenyl-substituted 3-(pyridin-2-yl)-1,2,4-triazines / T. D. Moseev, M. V. Varaksin, E. A. Nikiforov [et al.] // Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - P274-276 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIDO[1,2-A]INDOLES -- ARYNE -- REARRANGEMENT |
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 |