O-57 One-Step Heterylation at the Upper Rim of Calix[4]arene with 1,2,4-Triazin-5(2H)-ones [Electronic resource] / D. G. Beresnev, N. A. Itsikson, O. N. Chupakhin, V. N. Charushin, M. I. Kodess, A. I. Butakov, G. L. Rusinov, Yu. Yu. Morzherin, A. I. Konovalov, I. S. Antipin // Journal of Organic Chemistry. - 2006. - Vol. 71, № 21. - P8272-8275 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient way to modify calix[4]arenes based on the direct C-C coupling reaction of their phenol moiety with 1,2,4-triazines has been advanced, and the ability of modified calixarenes to provide transport of La3+ and Ga3+ cations through organic membranes has been examined. ?? \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2006, v.71, N 21, p.8272.pdf |
E 31 Egorov, I. N. The direct arylation of 1,3,5-triazin-2,4(1H,3H)-dione [Text] / I. N. Egorov, V. L. Rusinov, O. N. Chupakhin // Tetrahedron Letters. - 2010. - Vol. 51, № . - P1717-1718 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Direct introduction of non-activated arenes to 1,3,5-triazin-2,4(1H,3H)-dione in the presence of AlCl3 is described \\\\Expert2\\nbo\\Tetrahedron Letters\\2010, v.51, p.1717.pdf |
E 27 Effective fluoroalkylation of aldehydes by delta-perfluoroalkyl-iron compounds [Text] / V. G. Ratner, V. B. Korolev, D. L. Chizhov, K. I. Pashkevich // Journal of Fluorine Chemistry. - 1992. - Vol. 58, № 2-3. - P355 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Organoiron compounds with ?-perfluoroalkyl-iron bonds are well-known and common compounds convenient to prepare and handle. However, their application in organic synthesis was restricted to the introduction of fluoroalkyl group only into electron rich organic molecules such as arenes and thiols |
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 |
8,9,10-Trifluoro-6-oxo-6H-pyrido[1,2-a]quinoline-5-carbonitrile in the synthesis of novel 1-heteryl-3,3-dimethyl-3,4-dihydroisoquinolines [Electronic resource] / T. S. Vshivkova, Yu. V. Shklyaev, E. V. Nosova, G. N. Lipunova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2012. - Vol.61, №8. - С. 1650-1652. - Bibliogr. : p. Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 3,4-dihydroisoquinolines -- THREE-COMPONENT CONDENSATION -- ISOBUTYRALDEHYDE Аннотация: 3,4-Dihydroisoquinolines containing the 8,9,10-trifluoro-6H-pyrido[1,2-a]quinolin-6-one substituent in position 1 were obtained by three-component reactions between arenes, isobutyraldehyde, and 8,9,10-trifluoro-6-oxo-6H-pyrido[1,2-a]quinoline-5-carbonitrile in H2SO4 \\\\expert2\\NBO\\Russian Chemical Bulletin\\2012, 61 (8), 1650-1652.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 |
T 44 The synthesis of polyarene-modified 5-phenyl-2,2'-bipyridines via the methodology and aza-Diels-Alder reaction [Electronic resource] / I. S. Kovalev, D. S. Kopchuk, A. F. Khasanov, V. L. Rusinov, O. N. Chupakhin // Mendeleev Communications. - 2014. - Vol.24, №2. - С. 117-118. - Bibliogr. : p. 118 (52 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TRIAZINE -- LIGANDS -- ARENES Аннотация: Nucleophilic substitution of hydrogen () in 6-phenyl-3-(2-pyridyl)-1,2,4- triazine under the action of lithium derivatives of polynuclear arenes followed by aza-Diels-Alder reaction with norbornadiene or morpholinocyclopentene gives the novel polyarenemodified photoluminescent 5-phenyl-2,2'-bipyridine ligands \\\\expert2\\nbo\\Mendeleev Communications\\2014, v.24, p. 117-118.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 |
T 98 Two Approaches in the Synthesis of Planar Chiral Azinylferrocenes [Electronic resource] / I. A. Utepova, O. N. Chupakhin, P. O. Serebrennikova, A. A Musikhina, V. N. Charushin // Journal of Organic Chemistry. - 2014. - Vol. 79, № 18. - С. 8659-8667. - Bibliogr. : p. 8666-8667 (34 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHIRAL AZINYLFERROCENES -- CROSS-COUPLING REACTION -- HALOGENATED AZINES Аннотация: Two synthetic routes to the chiral azinylferrocenes (CAFs) 5 and 15, key intermediates for the synthesis of new enantiomerically enriched P,N-ligands, have been compared. The first approach is based on the palladium-catalyzed cross-coupling reaction of halogenated azines with organozinc derivatives of ferrocenes (the Negishi reaction). The second approach exploits a new synthetic methodology, which provides a shorter pathway, through the direct C–H functionalization of aromatics by the C–C coupling of halogen-free (hetero)arenes with lithium ferrocenes bearing stereogenic C and S atoms. The palladium complexes of P,N-ligands have been used as catalysts for the Tsuji–Trost reaction, which proceeds with high enantioselectivity to give allylic substitution products in good yields. \\\\expert2\\nbo\\Journal of Organic Chemistry\\2014, v.79, p.8659.pdf |
O-57 One-Pot, Three-Component Synthesis of Novel Pyrroloacridinones via Intramolecular ipso Dearomatization–Intramolecular Aza-Michael Addition Sequence [Electronic resource] / Y. S. Rozhkova, K. A. Galata, A. A. Gorbunov, Yu. V. Shklyaev, M. A. Ezhikova, M. I. Kodess // Synlett. - 2014. - Vol. 25, № 18. - С. 2617-2623 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): INTRAMOLECULAR IPSO DEAROMATIZATION -- SPIRO-SUBSTITUTED CYCLOHEXA-2,5-DIENONE -- DOMINO REACTION Аннотация: A one-pot, three-component synthesis of novel pyrroloacridinones from a set of alkoxy arenes and 2,6-dialkylphenols, isobutyric aldehyde, and 2-aminobenzonitrile is described. We have demonstrated the efficacy of the combination of intramolecular electrophilic ipso dearomatization of suitable aromatic compounds leading to spiro-substituted cyclohexa-2,5-dienones and intramolecular aza-Michael addition for the preparation of complex aza-heterocyclic systems. \\\\expert2\\nbo\\Synlett\\2014, V.25, p. 2617.pdf |
S 70 Solvent-free synthesis of pillar[6]arenes [Electronic resource] / S. Santra, D. S. Kopchuk, I. S. Kovalev, G. V. Zyryanov, A. Majee, V. N. Charushin, O. N. Chupakhin // Green Chemistry. - 2016. - Vol. 18. - С. 423-426. - Bibliogr. : p. 5 (16 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PILLAR[6]ARENES -- SOLVENT-FREE PROCEDURE Аннотация: An efficient solvent-free procedure for the synthesis of pillar[6]arenes has been developed. The procedure involves the solid-state condensation of finely milled 1,4-dialkoxybenzene and paraformaldehyde by grinding in the presence of a catalytic amt. of H2SO4. The use of org. solvents for the extn. of products has also been avoided. Operational simplicity, compatibility with various 1,4-dialkoxybenzenes, non-chromatog. purifn. technique, high yields and mild reaction conditions are the notable advantages of this procedure. A large scale reaction demonstrated the practical applicability of this methodol. \\\\expert2\\nbo\\Green Chemistry\\2015. Accepted Manuscript. P. 1-5. pdf.pdf |
A 10 A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles [Electronic resource] / R. A. Irgashev, A. A. Karmatsky, G. L. Rusinov, V. N. Charushin // Beilstein Journal of Organic Chemistry. - 2015. - Vol. 11. - С. 1000-1007. - Bibliogr. : p. 1006-1007 (35 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALDOL-CROTONIC CONDENSATION -- LAWESSON'S REAGENT -- ISATIN Аннотация: A short and robust approach for the synthesis of 2-(hetero)aryl substituted thieno[2,3-b]indoles from easily available 1-alkylisatins and acetylated (hetero)arenes has been advanced. The two-step procedure includes the "aldol-crotonic" type of condensation of the starting materials, followed by treatment of the intermediate 3-(2-oxo-2-(hetero)arylethylidene) indolin-2-ones with Lawesson's reagent. The latter process involves two sequential reactions, namely reduction of the C=C ethylidene double bond of the intermediate indolin-2-ones followed by the Paal-Knorr cyclization, thus affording tricyclic thieno[2,3-b]indoles. \\\\expert2\\nbo\\Beilstein Journal of Organic Chemistry\\2015, v. 11, p.1000-1007.pdf |
R 74 Role of polar solvents for the synthesis of pillar[6]arenes [Electronic resource] / S. Santra, I. S. Kovalev, D. S. Kopchuk, G. V. Zyryanov, A. Majee, V. N. Charushin, O. N. Chupakhin // RSC Advances. - 2015. - Vol. 5, № 126. - С. 104278-104282. - Bibliogr. : p. 104282 (26 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HOST-GUEST COMPLEXATION -- WATER CHANNELS -- HIGH-YIELD SYNTHESIS Аннотация: An efficient procedure for the synthesis of pillar[6]arenes has been developed. The procedure involves the condensation of 1,4-dialkoxybenzenes and paraformaldehyde in the presence of a catalytic amount of H2SO4 or BF3 center dot OEt2 in polar solvent media (acetonitrile, ethyl alcohol, acetone etc.). In all cases the interaction afforded pillar[6]arenes in high yields. \\\\expert2\\nbo\\RSC Advances\\2015. Vol. 5, N 126. P. 104278-104282.pdf |
O-72 Organolithium compounds in the nucleophilic substitution of hydrogen in arenes and hetarenes [Electronic resource] / I. S. Kovalev, D. S. Kopchuk, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Russian Chemical Reviews. - 2015. - Vol. 84, № 12. - С. 1191-1225. - Bibliogr. : p. 1224-1225 (237 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NUCLEOPHILIC SUBSTITUTION -- HYDROGEN -- ARENES AND HETARENES Аннотация: The review considers the most typical examples of the direct non-activated non-catalytic C–C bond formation in arenes and their metal complexes activated by electron-withdrawing substituents in the aromatic nucleus and in hetarenes (azines and their N-oxides, porphyrins, etc.) upon the reactions with aliphatic and (hetero)aromatic (hetero)organolithium nucleophiles. Particular attention is given to the direct introduction of nitroxide radicals and (hetero)organic moieties into mono-, di- and triazines and their N-oxides. The influence of the structures of the (hetero)aromatic substrate and the (hetero)organolithium nucleophile on the reaction pathway and rate and on the structure of the reaction product is analyzed. \\\\expert2\\nbo\\Russian Chemical Reviews\\2015, V.84, N12, p. 1191-1225.pdf |
H 99 Hypervalent Iodine(III) in Direct Oxidative Amination of Arenes with Heteroaromatic Amines [Electronic resource] / S. Manna, P. O. Serebrennikova, I. A. Utepova, A. P. Antonchick, O. N. Chupakhin // Organic Letters. - 2015. - Vol. 17, № 18. - С. 4588-4591. - Bibliogr. : p. 4591 (15 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): N BOND FORMATION -- CROSS-COUPLING REACTIONS -- C-H AMINATION Аннотация: A novel, mild, and practical method of amination of simple nonfunctionalized arenes under metal free conditions has been developed. The approach allows coupling of electron-rich arenes with amino derivatives of electron-deficient heterocycles providing rapid access to scaffolds of bioactive compounds and is based on the application of the hypervalent iodine(III) reagent as an oxidant. Regioselective functionalization of C-H bonds of arenes by the formation of C-N bonds under organocatalytic conditions was demonstrated. \\\\expert2\\nbo\\Organic Letters\\2015, v.17, N 18, p.4588-4591.pdf |
S 98 Synthesis and characterizations of new cadmium complexes based on poly(aza)arene-annelated 2,2 '-bipyridines [Electronic resource] / D. S. Kopchuk, P. A. Slepukhin, I. S. Kovalev, A. F. Khasanov, O. S. Taniya, O. V. Shabunina, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin // Polyhedron. - 2016. - Vol. 110. - С. 235-240 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): Cd(II) COMPLEX -- 2,2 '-BIPYRIDINES -- POLY(AZA)ARENES Аннотация: We have developed an efficient synthesis of new cadmium(II)-containing complexes based on poly(aza) arene-annelated 2,2'-bipyridines. All the complexes were characterized by X-ray structural analysis. The influence of the type of the ligand at the structural properties of the complexes has been studied. \\\\expert2\\NBO\\Polyhedron\\2016, v.110, p.235-240.pdf |
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 |
Direct C−H functionalization of calix[N](het)arenes (N=4,6): a brief update / A. Mukherjee, D. S. Kopchuk, I. S. Kovalev [et al.] // ChemistrySelect. - 2022. - Vol. 7, № 12. - Pe202103017 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Calix[n]arenes, their hetero derivatives, are the most popular hosts for the supramolecular and materials chemistry as they can form stable inclusion complexes with charged or neutral molecules, including gases. This short review highlights the most prospective synthetic approaches for direct modification of calix[4]arene core with various functional moieties as well as selected patterns of direct C−H-modification of calix[6]arenes and calix[4]pyrroles. |
Oxidative C–H functionalization of arenes: main tool of 21st century green chemistry. A review / A. V. Shchepochkin, F. V. Antipin, V. N. Charushin, O. N. Chupakhin // Doklady Chemistry. - 2021. - Vol. 499, № 1. - P123-157 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Recent advances in the field of direct oxidative C–H functionalization of inactivated arenes, as one of the main tools of green chemistry, are discussed. Examples of building carbon–carbon, carbon–oxygen, carbon–nitrogen, and carbon–sulfur bonds, using catalysis with palladium compounds, oxidation with hypervalent iodine derivatives, and through electrochemical and photochemical transformations, are given. |