Д 26 9-Allyl-1,7-dicarbadodecaborane as a dienophile in aza Diels-Alder reactions of 1,2,4-triazines: synthesis of pyridines bearing a carborane cage [Electronic resource] / A. M. Prokhorov, P. A. Slepukhin, V. L. Rusinov, V. N. Kalinin, D. N. Kozhevnikov // Tetrahedron Letters. - 2008. - Vol. 49, № 23. - P3785-3789 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TRIAZINES -- PYRIDINES Аннотация: The synthesis of pyridine and bipyridine derivatives of m-carborane via aza Diels–Alder reaction of 1,2,4-triazines with 9-allyl m-carborane and their structural characterization and photophysical properties are described. The products 3- and 4-(m-carborane-9-ylmethyl)-2,2`-bipyridines form Zn(II) complexes on reaction with ZnCl2, which increases significantly their fluorescence intensity. \\\\Expert2\\nbo\\Tetrahedron Letters\\2008, v. 49, p.3785.pdf |
C 21 Carborane-Functionalized Polyaza Aromatic Ligands: Synthesis, Crystal Structure, and a Copper(II) Complex [Text] / A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin, I. V. Glukhov, M. Yu. Antipin, O. N. Kazheva, A. N. Chekhlov, O. A. Dyachenko // Organometallics. - 2006. - Vol. 25, № 12. - P2972-2977 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A consecutive aromatic nucleophilic substitutions of hydrogen in 1,2,4-triazine 4-oxides and an aza Diels?Alder reaction is a versatile route to carborane-functionalized bi- and terpyridines and their 1,2,4-triazine analogues. The heterocycles facilitate deboronation of the substituted carboranes, and the carborane moiety has a significant influence on the coordination properties of the ligands as well |
C 75 Consecutive nucleophilic substitution and aza Diels-Alder reaction-an efficient strategy to functionalized 2,2'-bipyridines [Electronic resource] / D. N. Kozhevnikov, V. N. Kozhevnikov, A. M. Prokhorov, M. M. Ustinova, V. L. Rusinov, O. N. Chupakhin, G. G. Aleksandrov, B. Koenig // Tetrahedron Letters. - 2006. - Vol. 47, № 6. - P869-872 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: An efficient strategy for the synthesis of functionalized 2,2`-bipyridines is reported. The strategy is based on readily available 3-pyridyl-1,2,4-triazine 4-oxides and uses a reaction sequence of nucleophilic substitution of hydrogen and aza Diels-Alder reaction. \\\\Expert2\\nbo\\Tetrahedron Letters\\2006, v. 47, p.869.pdf |
L 81 Lithiacarboranes and 1,2,4-triazine 4-oxides: SNH reactions and ring transformations [Electronic resource] / O. N. Chupakhin, A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, I. A. Glukhov, Z. A. Starikova, V. A. Ol'shevskaya, V. N. Kalinin, M. Yu. Antipin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1223-1231. - Библиогр. : с. 1231 (14 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 1-lithia-1,2- or 1,7-dicarba-closo-dodecaborane with 1,2,4-triazine 4-oxides can follow two competitive pathways: deoxygenative nucleophilic substitution of hydrogen to form 1-(1,2,4-triazin-5-yl)-1,2- or 1,7-dicarba-closo-dodecaboranes and the transformation of the 1,2,4-triazine ring into the triazoline ring giving rise to 1-(2-acetyl-1-aroyl-3-aryl-1,2,4-triazolin-5-yl)-1,2-dicarba-closo-dodecaboranes. Introduction of the electron-withdrawing triazine ring into the carborane cage substantially facilitates deboronation to give 1-(1,2,4-triazin-5-yl)-1,2-1,7-dicarba-nido-undecaboranes. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1223-1231.pdf |
A 94 Auto-aromatization of the sigma(H)-adducts of 1,2,4-triazine 4-oxides with carbanions in reactions of nucleophilic substitution of hydrogen [Electronic resource] / D. N. Kozhevnikov, A. M. Prokhorov, V. L. Rusinov, O. N. Chupakhin // Mendeleev Communications. - 2000. - Vol.10, N6. - P227-228 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 1,2,4-triazine 4-oxides react with stable carbanions to form 5-substituted 1,2,4-triazines as the products of deoxygenation nucleophilic substitution of hydrogen |
A 77 Aromatic nucleophilic substitution in 1,2,4-triazine 4-oxides with Grignard reagents [Text] / A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin // Polish Journal of Chemistry. - 2003. - Vol. 77, № 9. - P1157-1161 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Addition of the Grignard reagents to 1,2,4-triazine 4-oxides followed by aromatization of the intermediate ?H-adducts by dehydrogenation or dehydration was used for synthesis of 5-alkyl- or 5-aryl-substituted 1,2,4-triazines and their 4-oxides. |
T 44 The amidine rearrangement in 5-amino-6-aryl-1,2,4-triazine-4-oxides initiated by hydroxylamine [Text] / O. N. Chupakhin, V. N. Kozhevnikov, A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov // Tetrahedron Letters. - 2000. - Vol. 41, № 38. - P7379-7382 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
1,2,4-Triazinylcarboranes: a new approach to the synthesis and the crystal structures of 1-(3,6-ditolyl-1,2,4-triazin-5-yl)-2-phenyl-1,2-dicarba-closo-dodecaborane and 1,7-bis[6-phenyl-3-(4-chlorophenyl)-1,2,4-triazin-5-yl]-1,7-dicarba-closo-dodecaborane [Electronic resource] / O. N. Chupakhin, A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, V. N. Kalinin, V. A. Ol'shevskaya, I. A. Glukhov, M. Yu. Antipin // Mendeleev Communications. - 2003. - Vol. 13, № 4. - P165-167 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TRIAZINYLCARBORANES -- SYNTHESIS -- CRYSTAL STRUCTURES Аннотация: The reactions of the lithio derivatives of 1,2- or 1,7-dicarba-closo-dodecaboranes with 1,2,4-triazine 4-oxides represent a versatile synthetic approach to carboranes bearing heteroaromatic substituents?????? |
N 91 Nucleophilic substitution or dipolar 1,3-cycloaddition in reactions of cyanamide with 4-arylpyrimidine 1-oxides [Electronic resource] / A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 5. - P1195-1197 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Pyrimidine 1-oxides with cyanamide afforded 2-ureidopyrimidines as the result of the nucleophilic substitution of hydrogen, whereas the formation of similar 2-trichloroacetylaminopyrimidines occurs as dipolar 1,3-cycloaddition of the same oxides to trichloroacetonitrile under much more drastic conditions and in lower yields?? \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (5), 1195.pdf |
P 93 Prokhorov, A. M. CuCl2 induced reactions of 6-ethynyl- and 6-cyano-5-aryl-2,2-bipyridines with various N- and O-nucleophiles in comparison with the reactions of relative 1,2,4-triazines [Text] / A. M. Prokhorov, P. A. Slepukhin, D. N. Kozhevnikov // Journal of Organometallic Chemistry. - 2008. - Vol. 693, № 10. - P1886-1894 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Meanwhile 5-aryl-6-cyano-2,2-bipyridines are very stable towards various nucleophiles, addition copper(II) chloride to the reactional mixture facilitates nucleophilic addition to the cyano group dramatically. The cyanobipyridines react easily with water, methanol, ethanolamine in the presence of CuCl2 yielding well-crystallized complexes containing carboxylates, carboximidates or carboxamidines as ligands. 5-Cyano-1,2,4-triazines are more active in the reactions due to higher electron-withdrawing properties of this heterocycle. Due to the same reason acetylene moiety of 5-ethynyl-3-pyridyl-1,2,4-triazine adds water quite easily but in the presence of copper chloride as well \\\\Expert2\\nbo\\Journal of Organometallic Chemistry\\2008, v.693, p.1886.pdf |
P 93 Prokhorov, A. M. Direct introduction of acetylene moieties into azines by S(N)H methodology [Text] / A. M. Prokhorov, M. Makosza, O. N. Chupakhin // Tetrahedron Letters. - 2009. - Vol. 50, № 13. - P1444-1446 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the corresponding ethynylazines 2a–g. Reaction with lithium acetylide requires subsequent acylation of the intermediate anionic adduct for rearomatization whereas in the case of potassium acetylide, auto-aromatization takes place?? \\\\Expert2\\nbo\\Tetrahedron Letters\\2009, V. 50, N 13, p.1444.pdf |
N 91 Nucleophilic substitution of hydrogen vs 1,3-dipolar cycloaddition in reactions of azine N-oxides with cyanamide [Text] : доклад, тезисы доклада / O. N. Chupakhin, V. L. Rusinov, D. N. Kozhevnikov, A. M. Prokhorov // XXth European Colloquium on Heterocyclic Chemistry, Stockholm,Sweden, 18-21 Aug. 2002 г. - Stockholm, 2002. - PA:9 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
N 91 Nucleophilic substitution of hydrogen in the reaction of 1,2,4-triazin-4-oxides with cyanamide [Electronic resource] / V. N. Kozhevnikov, A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2000. - Vol. 49, № 6. - P1122-1124 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: It was shown that cyanamide can successfully be used in reactions of nucleophilic substitution of hydrogen with 1,2,4-triazin-4-oxides in the presence of a base to give 5-cyanoimino-1,2,4-triazines. It was found by13C NMR spectroscopy that these compounds and their alkylation products at the cyclic nitrogen atom exist in the form of 5-cyanoimino-2,5-dihydro-1,2,4-triazines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2000, 49 (6), 1122.pdf |
S 10 S-N(H) reactions of pyrazine N-oxides and 1,2,4-triazine 4-oxides with CH-active compounds [Electronic resource] / D. N. Kozhevnikov, I. S. Kovalev, A. M. Prokhorov, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 7. - P1588-1594 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Nucleophilic substitution of hydrogen in pyrazine N-oxides under the action of CH-active compounds requires activation with acylating agents. This activation facilitates aromatization of intermediate H adducts via elimination of the acid residue to form substituted pyrazines. More electrophilic 1,2,4-triazine 4-oxides react with carbanions derived from CH-active compounds without additional activation according to a scheme, which has previously been unknown for azine N-oxides. This scheme involves aromatization of H adducts through elimination of water by the E1cb mechanism. The reaction products occur in DMSO-d6 solutions predominantly as 6-methylene-1,6-dihydropyrazines and 5-methylene-4,5-dihydro-1,2,4-triazines.??nucleophilic substitution of hydrogen - 1,2,4-triazine 4-oxide - pyrazine 1-oxide - carbanion - CH-active compounds?? \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (7), 1588.pdf |
I-60 Influence of pi stacking on the magnetic properties of the copper(II) complex with 6-phenyl-3-(2-pyridyl)-5-trifluoroacetylmethylidene-4,5-dihydro-1,2,4-triazine [Electronic resource] / A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin, G. G. Aleksandrov, Yu. N. Shvachko, D. V. Starichenko, A. V. Korolev, D. V. Bukhvalov, V. V. Ustinov // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 3. - P561-566 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The new N,N,O-ligand 6-phenyl-3-(2-pyridyl)-5-(trifluoroacetylmethylidene)-4,5-dihydro-1,2,4-triazine (L) was synthesized, and its complex with CuII was prepared. The structure of the complex was established by X-ray diffraction. Magnetic measurements and ESR studies were carried out. Ab initio calculations of the electronic structure, exchange interactions, and the effective magnetic moment were performed. The intrastack polarization effect between the ? states of 1,2,4-triazine and the d states of copper was revealed and numerically validated \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (3), 561.pdf |
5-Acylmethyl-3-(2-pyridyl)-1,2,4-triazines: Synthesis and Complexes with Cu(II) [Electronic resource] / A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, A. I. Matern, M. M. Nikitin, O. N. Chupakhin, I. L. Eremenko, G. G. Aleksandrov // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 11. - P1702-1705 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 5-Acylmethyl-3-(2-pyridyl)-1,2,4-triazines are easily prepared from accessible 3-(2-pyridyl)-1,2,4-triazine 4-oxides by reaction of the latter with acetophenone or trifluoroacetone in the presence of NaH. The compounds obtained behaved as efficient ligands in reaction with CuCl2 furnishing dimeric neutral complexes with Cu(II) whose structure was investigated by means of X-ray diffraction analysis \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2005, 41 (11), 1702-1705.pdf |
1,2,4-Triazine method of bipyridine ligand synthesis for the preparation of new luminescent Eu(III) complexes [Text] / A. M. Prokhorov, V. N. Kozhevnikov, D. S. Kopchuk, D. N. Kozhevnikov // Tetrahedron. - 2011. - Vol. 67, № 3. - P597-607 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The ‘triazine’ methodology for the synthesis of functionalised bipyridine ligands proved to be a convenient method for the preparation of luminescent Eu(III) complexes. The approach allows flexible construction of chromophore and coordination sphere with control of photophysical properties. Europium (III) complexes [Eu1]-[Eu5] prepared in this way exhibit intense long-life metal-centered luminescence in aqueous media. The aromatic substituent in the position 5 of bipyridine has a significant influence on luminescence parameters and is used to introduce functionality for bioconjugation. The complexes [Eu4] and [Eu5] bearing primary amine groups are ready-to-go luminescent ‘tags’ for peptide labeling \\\\Expert2\\nbo\\Tetrahedron\\2011, v. 67, p. 597.pdf |
K 80 Kozhevnikov, D. N. Triazines, Tetrazines and Fused Ring Polyaza Systems [Text] / D. N. Kozhevnikov, A. M. Prokhorov // Progress in Heterocyclic Chemistry. - 2011. - Vol. 22. - P427-447 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
L 96 Luminescent metallocomplexes of functionalized pyridines : from ligand design towards special properties [Text] : доклад, тезисы доклада / D. N. Kozhevnikov, D. S. Kopchuk, M. Z. Shafikov, A. M. Prokhorov // International conference "Topical Problems of Organometallic and Coordination Chemistry", V Razuvaev lectures, N. Novgorod, September 3-9 2010 : book of abstracts . - Nizhny Novgorod, 2010. - S13 : рис. Рубрики: ХИМИЧЕСКИЕ НАУКИ |
2,2 '-Bipyridinyl carboranes as B,N,N-ligands in cyclometallated complexes of platinum(II) [] / A. M. Prokhorov, P. A. Slepukhin, V. L. Rusinov, V. N. Kalinin, D. N. Kozhevnikov // Chemical Communications. - 2011. - Vol. 47, № 27. - С. 7713-7715 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): O-CARBORANE -- METALLACARBORANES -- PHOTOLUMINESCENT Аннотация: Novel B,N,N-cyclometallated Pt(II) complexes of 2,2'-bipyridin-6-yl carboranes exhibit absorption and emission similar to relative Pt(II) complexes of aromatic C,N,N-ligands: the same transitions but lower intensities. DFT calculations suggest the former emits from the (3)MLCT state while for the latter the mixed (3)ICT-MLCT transitions should be considered \\\\expert2\\NBO\\Chemical Communications\\2011,v.47. p.7713.pdf |