S 98 Synthesis of carborane analogues of gamma-aminobutanoic acid [Text] / V. A. Ol'shevskaya, R. Ayuob, Z. G. Brechko, P. V. Petrovskii, G. L. Levit, V. P. Krasnov, V. N. Charushin, O. N. Chupakhin, V. N. Kalinin // Journal of Organometallic Chemistry. - 2005. - Vol. 690, № 11. - P2761-2765 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: General method for preparation of high yields of novel N-protected carborane amino acid derivatives, 3-acylamino-1-carboxymethyl-2-R-o-carboranes (R = H, Me, Ph), is reported. The synthesis starts from readily available 3-amino-o-carboranes and includes the protection of amino group, introduction of carboxymethyl function to the carbon atom of polyhedron via the metallation of carborane CH bond with sodium amide in liquid ammonia, and treatment of corresponding sodium carboranes with sodium bromoacetate. Deprotection of N-acylated carborane amino acids is studied in acidic media. Depending on the procedure employed, closo- or nido-carborane amino acids were obtained \\\\Expert2\\nbo\\Journal of Organometallic Chemistry\\2005, v. 690, p.2761.pdf |
D 47 Determination of enantiomeric purity of 1-substituted 3-amino-1,2-dicarba-closo-dodecaboranes by HPLC on chiral stationary phases [Electronic resource] / V. P. Krasnov, A. M. Demin, G. L. Levit, L. Sh. Sadretdinova, A. N. Grishakov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 12. - P2535-2539 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A determination of enantiomeric purity of 1-substituted (Me, Ph, and Pri) 3-amino-1,2dicarba-closo-dodecaboranes by HPLC on chiral Chiralcel OD-H and Chiralpac AD stationary phases involving preliminary phthaloylation of 3-aminocarboranes has been suggested as a general method \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (12), 2535.pdf |
S 98 Synthesis of N-[(3-Amino-1,2-dicarba-closo-dodecaboran-1-yl)acetyl] Derivatives of alfa-Amino Acids [Text] / G. L. Levit, V. P. Krasnov, D. A. Gruzdev, A. M. Demin, I. V. Bazhov, O. N. Chupakhin, V. N. Charushin // Collection of Czechoslovak Chemical Communications. - 2007. - Vol. 72, № 12. - P1697-1706 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The N-[(3-amino-1,2-dicarba-closo-dodecaboran-1-yl)acetyl] derivatives of amino acids were prepared starting from N-protected (Ac, Form, Bz, and Boc) 3-amino-1-(carboxymethyl)-o-carboranes and alkyl esters of natural amino acids using the carbodiimide method of coupling and removing the ester groups. All the amides obtained were diastereoisomeric mixtures. Some diastereoisomers were separated and the assignment of the absolute configuration of aminocarborane fragments was performed by X-ray crystallography |
1,3-Dipolar cycloaddition of [(o-carboran-1-yl)methyl]azide to alkynes [Text] / V. A. Ol'shevskaya, E. V. Verbitskiy, G. L. Rusinov, V. N. Kalinin, V. N. Charushin // Doklady Chemistry. - 2010. - Vol. 434, № 2. - P245-248 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HETEROCYCLIC SYSTEMS -- CLOSO-CARBORANES -- CARBORANES \\\\Expert2\\nbo\\Doklady Chemistry\\2010, v. 434, N 1, p. 245-248.pdf |
E 54 Enantiomers of 3-amino-1-methyl-1,2-dicarba-closo-dodecarborane [Text] : доклад, тезисы доклада / V. P. Krasnov, G. L. Levit, V. N. Charushin, A. N. Grishakov, V. A. Ol'shevskaya, V. N. Kalinin, O. N. Chupakhin // Eleventh International Conference on Boron Chemistry "IMEBORON XI", M., July 28-Aug.2, 2002 : abstracts. - M., 2002. - 119 (P-41) Рубрики: ХИМИЧЕСКИЕ НАУКИ |
K 46 Kinetic resolution of 1-substituted 3-amino-1,2-dicarba-closo-dodecarboranes [Text] : доклад, тезисы доклада / V. P. Krasnov, G. L. Levit, A. M. Demin, M. I. Kodess, V. A. Ol'shevskaya, V. N. Kalinin, V. N. Charushin, O. N. Chupakhin // Euroboron 3, The 3rd European Meeting on Boron Chemistry, Pruhonice-by-Prague, Czech Republic, 12-16 Sept. 2004 : abstr. . - Pruhonice-by-Prague, Czech Republic, 2004. - P38 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
H 99 Hydrolysis of 1-methyl- and 1-phenyl-3-amino-1,2-dicarba-closo-dodecarborane amides [Text] : доклад, тезисы доклада / G. L. Levit, A. M. Demin, M. I. Kodess, M. A. Ezhikova, L. Sh. Sadretdinova, V. A. Ol'shevskaya, V. N. Kalinin, V. P. Krasnov, V. N. Charushin // Euroboron 3, The 3rd European Meeting on Boron Chemistry, Pruhonice-by-Prague, Czech Republic, 12-16 Sept. 2004 : abstr. . - Pruhonice-by-Prague, Czech Republic, 2004. - P39 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
N 89 Novel bis[(1,2,3-triazolyl)methyl]carborane derivatives via regiospecific copper-catalyzed 1,3-dipolar cycloaddition / V. A. Ol'shevskaya, E. V. Verbitskiy, G. L. Rusinov, V. N. Charushin, Evamarie Hey-Hawkins // Polyhedron. - 2012. - Vol.42, №1. - С. 302-306 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CARBORANES -- CARBABORANES -- TRIFLATES Аннотация: 1,2-Bis(azidomethyl)-о-carborane and 1,7-bis(azidomethyl)-m-carborane, prepared from the corresponding carboranylmethyl triflates and sodium azide, were conveniently functionalized by azide–alkyne cycloaddition affording novel bis[(1,2,3-triazolyl)methyl]carborane derivatives. Regiospecificity of this process was achieved by employing copper(II) acetate hydrate. Reaction of bis[(1,2,3-triazolyl)methyl]carborane derivatives with MeI yielded 3-methyl-1,2,3-triazolium carborane salts \\\\Expert2\\nbo\\Polyhedron\\2012. v.42. p.302.pdf |
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 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. |
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 |
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. |
Synthesis, characterization, and in vitro assessment of cytotoxicity for novel azaheterocyclic nido-carboranes – Candidates in agents for boron neutron capture therapy (BNCT) of cancer / M. V. Varaksin, L. A. Smyshliaeva, V. L. Rusinov [et al.] // Tetrahedron. - 2021. - Vol. 102. - P132525 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
1,3,7-triazapyrene-based ortho-carborane fluorophores: convenient synthesis, theoretical studies, and aggregation-induced emission properties / L. A. Smyshliaeva, M. V. Varaksin, E. I. Fomina [et al.] // Organometallics. - 2021. - Vol. 40, № 16. - P2792-2807 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient transition-metal-free approach, based on nucleophilic substitution of hydrogen (SNH), for consecutive regioselective C–H functionalization of 1,3,7-triazapyrene scaffolds with carboranyllithium and phenyllithium is reported. The theoretical calculations disclosed highlight key features in the regioselectivity and mechanism of the investigated SNH transformations. The novel 1,3,7-triazapyrene-based ortho-carboranes obtained have large potential in the field of molecular electronics as organic luminophores, which are characterized by the aggregation-induced emission and dual-emission effects. |