F 12 Facile Synthesis of 6-aryl-3-pyridyl-1,2,4-triazines as a key step towards hightly fluorescent 5-substituted bipyridines and their Zn(II) and Ru(II) complexes [Electronic resource] / V. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, M. M. Ustinova, B. Konig, D. N. Kozhevnikov // Tetrahedron. - 2008. - Vol. 64, № 37. - P8963-8973 : рис., табл. - Библиогр. : с. 8973 (21 назв.) . - ISSN 0040-4020 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A wide series of substituted bipyridines were obtained through the synthesis of 1,2,4-triazines and their aza Diels–Alder reactions. The reported method facilitates the synthesis of functionally diverse bipyridines that provides fine-tuning of photophysical properties of new ligands and their Zn(II) and Ru(II) complexes. Some of substituted bipyridines exhibit ‘off–on’ fluorescence response toward Zn2+ cations.???? \\\\Expert2\\nbo\\Tetrahedron\\2008, v. 64, N37, p. 8963.pdf |
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 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 |
S 98 Synthesis, structure and luminescence of ruthenium complexes with 6-cyano-2,2'-bipyridines [Electronic resource] / V. N. Kozhevnikov, D. N. Kozhevnikov, O. V. Shabunina, V. L. Rusinov, O. N. Chupakhin, M. Zabel, B. Koenig // Mendeleev Communications. - 2005. - Vol. 15, № 1. - P6-8 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The crystallographic data, NMR and UV-VIS spectra and luminescence of the heteroleptic complexes [Ru(L)(bpy)2](PF6)2 (L = 5-aryl-6-cyano-2,2'-bipyridine) are described. \\\\Expert2\\nbo\\Mendeleev Communications\\2005, v.15,p.6.pdf |
A 53 An efficient route to 5-(hetero)aryl-2,4'- and 2,2'-bipyridines through readily available 3-pyridyl-1,2,4-triazines [Electronic resource] / V. N. Kozhevnikov, D. N. Kozhevnikov, O. V. Shabunina, V. L. Rusinov, O. N. Chupakhin // Tetrahedron Letters. - 2005. - Vol. 46, № 11. - P1791-1793 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A new route to substituted bipyridines based on a new method for the synthesis of substituted 3-pyridyl-1,2,4-triazines and their aza-Diels-Alder reactions is shown to be an efficient strategy for the preparation of structurally diverse bipyridine ligands. \\\\Expert2\\nbo\\Tetrahedron Letters\\2005, v. 46, p.1791.pdf |
S 98 Synthesis of functionalised bipyridines by sequential nucleophilic substitution of hydrogen and cycloaddition in 1,2,4-triazine rings [Electronic resource] / D. N. Kozhevnikov, V. N. Kozhevnikov, T. V. Nikitina, V. L. Rusinov, O. N. Chupakhin, H. Neunhoeffer // Mendeleev Communications. - 2002. - Vol. 12, № 1. - P30-31 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- BIPYRIDINES -- TRIAZINE Аннотация: A new methodology for the synthesis of functionalised bipyridines by the direct cyanation of 3-(2-pyridyl)-1,2,4-triazine 4-oxide through nucleophilic substitution for hydrogen followed by the transformation of the 1,2,4-triazine ring into the pyridine ring by the Diels–Alder reaction and, finally, the chemical conversion of the cyano group is described |
5-Aryl-2,2-bipyridines as tunable fluorophores [Text] / D. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, P. A. Slepukhin, V. N. Kozhevnikov // Tetrahedron Letters. - 2006. - Vol. 47, № 39. - P7025-7029 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Readily available 5-aryl-2,2?-bipyridines and their derivatives are a unique family of fine-tunable chromophores, where changes in the substitution patterns, solvation and coordination are translated into dramatic spectral changes. They exhibit sensitive and selective response to zinc ions with dramatic increases in emission intensity or significant red-shifts of emission maxima???? \\\\Expert2\\nbo\\Tetrahedron Letters\\2006, v. 47, p.7025.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 |
A 89 Asymmetric cyclopalladation of 6-ferrocenyl-2,2-bipyridine and 2-ferrocenyl-1,10-phenanthroline [Electronic resource] / L. A. Bulygina, V. I. Sokolov, I. A. Utepova, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2007. - Vol. 56, № 5. - P1080-1082 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Cyclopalladation of 6-ferrocenyl-2,2?-bipyridine and 2-ferrocenyl-1,10-phenanthroline in the presence of the N-acylamino acid salt as the asymmetric catalyst was performed. Some reactions of the resulting bicyclic palladium derivatives with tridentate (N,N,C) ligands were studied \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2007, 56 (5), 1080-1082.pdf |
D 46 Design of ICT-PET fluorescent probes for zinc(II) based on 5-aryl-2,2′-bipyridines / D. S. Kopchuk, A. M. Prokhorov, P. A. Slepukhin, D. N. Kozhevnikov // Tetrahedron Letters. - 2012. - Vol.53, №46. - С. 6265-6268 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ZINC(II) SENSOR -- BIPYRIDINES -- INTRAMOLECULAR CHARGE TRANSFER Аннотация: Rational design of selective and sensitive ‘off-on’ fluorescent probes for Zn(II) cations exploiting both PET and ICT mechanisms of sensing is illustrated by the synthesis and application of 5-aryl-2,2′-bipyridines modified with a dipicolylaminomethyl fragment. The aryl substituent provides tuning of the prop \\\\Expert2\\nbo\\Tetrahedron Letters\\2012, v. 53, p. 6265.pdf |
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 |
P 91 Preparation of 5,6A '-diaryl-2,2A '-bipyridines using a 1,2,4-triazine methodology [Electronic resource] / D. S. Kopchuk, N. V. Chepchugov, G. A. Kim, G. V. Zyryanov, I. S. Kovalev, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2015. - Vol. 64, № 4. - С. 897-900. - Bibliogr. : p. 900 (26 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,4-TRIAZINES -- 5,6 '-DIARYL-2,2 '-BIPYRIDINES -- DIELS-ALDER REACTIONS Аннотация: New unsymmetric 5,6A '-diaryl-2,2A '-bipyridines were synthesized in high yields using a 1,2,4-triazine methodology. Their photophysical properties were studied. \\\\expert2\\nbo\\Russian Chemical Bulletin\\2015, 64 (4), 897-900.pdf |
S 98 Synthesis of unsymmetric 6,6 '-diaryl-2,2 '-bipyridines using a 1,2,4-triazine methodology [Electronic resource] / D. S. Kopchuk, N. V. Chepchugov, G. A. Kim, G. V. Zyryanov, I. S. Kovalev, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2015. - Vol. 64, № 3. - С. 695-698. - Bibliogr. : p. 698 (39 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,4-TRIAZINES -- 6,6 '-DIARYL-2,2 '-BIPYRIDINES -- DIELS-ALDER REACTIONS Аннотация: New unsymmetric 6,6'-diaryl-2,2'-bipyridines were synthesized in high yields using a "1,2,4-triazine" methodology. Their photophysical properties were studied. \\\\expert2\\nbo\\Russian Chemical Bulletin\\2015, 64 (3), 695-698.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 |
S 70 Solvent-free synthesis of 5-(aryl/alkyl)amino-1,2,4-triazines and α-arylamino-2,2′-bipyridines with greener prospects / D. S. Kopchuk, N. V. Chepchugov, I. S. Kovalev, S. Santra, M. Rahman, G. V. Zyryanov, V. N. Charushin, O. N. Chupakhin, K. Giri, A. Majee // RSC Advances. - 2017. - Vol. 7, № 16. - P9610-9619 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A green and highly efficient method has been developed for the synthesis of 5-(aryl/alkyl)amino-1,2,4- \\\\Expert2\\NBO\\RSC Advances\\2017 v.7 p.9610-9619.pdf |
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. |
Novel pentafluorophenyl- and alkoxyphenyl-appended 2,2'-bipyridine push-pull fluorophores: a convenient synthesis and photophysical studies / T. D. Moseev, E. A. Nikiforov, M. V. Varaksin [et al.] // Synthesis. - 2021. - Vol. 53, № 19. - P3597-3607 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 2,2′-BIPYRIDINES -- 1,2,4-TRIAZINES -- POLYFLUOROARENES Аннотация: A convenient method for the synthesis of new highly in non-polar solvents soluble photoactive pentafluorophenyl-substituted and extended alkoxyphenyl-substituted 2,2′-bipyridines is reported. The synthetic strategy for the preparation of such ligands involves a sequence of several structural transformations, such as O-alkylation, nucleophilic substitution of hydrogen (SN H) in 1,2,4-triazine precursors via the ‘addition–elimination’ scheme, and the subsequent conversion of the obtained 1,2,4-triazines into 2,2′-bipyridines by means of the aza-Diels–Alder reaction. The photophysical properties of the synthesized novel pentafluoroaryl-substituted 2,2′-bipyridines were comprehensively studied. The obtained photophysical data indicate the competitive advantages of the herein reported pentafluoroarylated push–pull fluorophores, bearing extended aliphatic moieties, over their analogues containing benzoxy or phenolic fragments in terms of improvement in quantum yield and well-pronounced positive solvatochromism confirmed by the mathematical analysis according to the Lippert–Mataga equation. |
Promising antifungal and antibacterial agents based on 5-aryl-2,2'-bipyridines and their heteroligand salicylate metal complexes: synthesis, bioevaluation, molecular docking / Y. V. Burgart, E. V. Shchegolkov, I. V. Shchur [et al.] // Chemmedchem: chemistry enabling drug discovery. - 2022. - Vol. 17, № 3. - Pe202100577 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A series of new 5-aryl-2,2′-bipyridines and their (polyfluoro)salicylate metal complexes was synthesized. Their antimicrobial activity was evaluated in vitro against eight strains of dermatophytes, seven strains of Candida yeasts, eight strains of Gram-positive and two strains of Gram-negative bacteria. Using molecular docking, we proposed that anti-staphylococcal action proceeds through the inhibition mechanism of the leading compounds to S. aureus DNA gyrase GyrB. |
The synthesis of aminophenyl-substituted 2,2′-bipyridine ligands by “1,2,4-triazine” methodology / A. P. Krinochkin, D. S. Kopchuk, M. I. Savchuk [et al.] // AIP Conference Proceedings. - 2021. - Vol. 2388, № 1. - Ст. 030016 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient synthetic approach to the 2,2’-bipyridines, including those with a condensed cyclopentene fragment, having an aminophenyl substituent at the C5 or C6 positions is reported. The products were obtained via their 1,2,4-triazine analogs with a nitro group, by the subsequent transformation of their 1,2,4-triazine ring into a pyridine one and the reduction of the nitro group to the amino group. |
Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties / A. D. Sharapov, R. F. Fatykhov, I. A. Khalymbadzha [et al.] // Chimica Techno Acta. - 2023. - Vol. 10, № 4. - P202310417 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHEMOSENSORS -- COUMARINS -- 2,2’-BIPYRIDINES Аннотация: In this work, we report the synthesis of novel coumarin-bipyridine conjugates using a sequence of C-C coupling reaction between 5,7-dimethoxycoumarins and 3-pyridyl-6-aryl-1,2,4-triazines followed by the Boger reaction with norbornandiene to obtain 8-[2,2'-bipyridyl]-5,7-dimethoxycoumarins. Photophysical properties were investigated for the obtained series of 8-[2,2'-bipyridyl]-5,7-dimethoxycoumarins: absorption and emission wavelength maxima are in the region of 212-296 and 401-410 nm, respectively; Stokes shifts are up to 116 nm, and fluorescence quantum yields are up to 15.0%. It was found that titrating the conjugates with Al3+, Zn2+, and Cd2+ ions results in an increase in the intensity of the emission maxima of the complexes, while the opposite effect was observed in the case of titration with Cu2+ ions. These findings suggest that the studied compounds may be considered as promising chemosensing materials. Finally, a positive solvatochromism of 8-[2,2'-bipyridyl]coumarins and their metal complexes was established. The experimental data are supported by mathematical calculations according to the Lippert-Matagaequation and Kosower diagram. |