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 Найдено в других БД:Публикации Чарушина В.Н. (37)
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1.
Инвентарный номер: нет.
   

   
    Expedient synthesis of 1,2,4-triazinyl substituted benzo[c]coumarins via double oxidation strategy / R. F. Fatykhov, I. A. Khalymbadzha, A. D. Sharapov [et al.] // Chimica Techno Acta. - 2023. - Vol. 10, № 2. - P202310205
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
COUMARIN -- 1,2,4-TRIAZINE -- NUCLEOPHILIC SUBSTITUTION OF HYDROGEN
Аннотация: Herein, we report a convenient one-pot synthesis of 1,2,4-triazinyl derivatives of benzocoumarins. The proposed approach consists of the nucleophilic addition of tetrahydrobenzo annulated dimethoxycoumarin to 1,2,4-triazines followed by double oxidation of both dihydrotriazine and tetrahydrobenzo groups with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The nucleophilic addition of the dimethoxycoumarin to 1,2,4-triazines was carried out in the presence of three-fold excess of methanesulfonic acid in DCM at room temperature. It takes place between positions 8 and 5 of coumarin and 1,2,4-triazine, respectively. The double oxidation step was carried out with 3.6 equivalent of DDQ. Selective oxidation of dihydrotriazine moiety, without affecting the tetrahydrobenzo fragment, was achieved using 1.2 equivalent of tetrachlorobenzoquinone (TCQ). The differences in the oxidation with TCQ and DDQ appear to be related to the higher oxidative potential of DDQ in contrast to TCQ. The advantages of the method are the elimination of the use of transition metals, the availability of starting materials, and the simplicity of the procedure. The proposed approach provides a two-step one-pot protocol for the synthesis of triazinyl benzocoumarins, precursors for the preparation of push-pull pyridinyl chromophore.

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2.
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    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.

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3.
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    Transformations of 4,5-bis(trifluoromethyl)imidazolidin-2-one and its N-substituted analogous in reactions with N,N-dinucleophiles / L. V. Saloutina, A. Y. Zapevalov, M. I. Kodess [et al.] // AIP conference proceedings. - 2022. - Vol. 2390. - Ст. 020069
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CHEMICAL COMPOUNDS
Аннотация: 4,5-Dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one and its N-methyl(phenyl)-substituted analogous were synthesized by the reaction of perfluorobiacetyl with urea and methyl(phenyl)urea. Depending on a solvent nature and character of the substituent at N-atom of the imidazolidine, different trifluoromethyl-containing heterocycles were obtained in reactions of the imidazolidin-2-ones with thiosemicarbazide and guanidine carbonate: imidazothiazol, 1,2,4-triazines, and hydantoins.

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4.
Инвентарный номер: нет.
   

   
    15N chemical shifts and Jnn-couplings as diagnostic tools for determination of the azide-tetrazole equilibrium in tetrazoloazines / S. L. Deev, T. S. Shestakova, Z. O. Shenkarev [et al.] // Journal of Organic Chemistry. - 2022. - Vol. 87, № 1. - P211–222
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Selectively 15N-labeled tetrazolo[1,5-b][1,2,4]triazines and tetrazolo[1,5-a]pyrimidines bearing one, two, or three 15N labels were synthesized. The synthesized compounds were studied by 1H, 13C, and 15N NMR spectroscopy in DMSO and TFA solutions, where the azide–tetrazole equilibrium can lead to the formation of two tetrazole (T, T′) isomers and one azide (A) isomer for each compound. Incorporation of the 15N-label(s) leads to the appearance of 15N–15N coupling constants (JNN), which can be easily measured via simple 1D 15N NMR spectra, even at natural abundance between labeled and unlabeled 15N atoms. The chemical shifts for the 15N nuclei in the azole moiety are very sensitive to the ring opening and azide formation, thus providing information about the azido–tetrazole equilibrium. At the same time, the 1–2JNN couplings between 15N-labeled atoms in the azole and azine fragments unambiguously determine the fusion type between tetrazole and azine rings in the cyclic isomers T and T′. Thus, combined analysis of 15N chemical shifts and JNN values in selectively isotope-enriched compounds provides an effective diagnostic tool for direct structural determination of tetrazole isomers and azide form in solution. This method was found to be the most simple and efficient way to study the azido–tetrazole equilibrium.

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5.
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    4-Hydroxy-3-nitro-1,4-dihydrotriazolo[5,1-c][1,2,4]triazines: synthesis, antiviral activity, and electrochemical characteristics / R. A. Drokin, E. A. Fesenko, P. N. Mozharovskaia [et al.] // Russian chemical bulletin. - 2022. - Vol. 71, № 11. - P2460-2466
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A new method for preparation of 4-hydroxy-3-nitro-1,4-dihydrotriazolo[5,1-c][1,2,4]-triazines using 1-nitro-2-morpholinoethylene and 3-diazo-1,2,4-triazoles is proposed. Antiviral activity against the Coxsackie B3 virus and electrochemical transformations of the prepared compounds are studied.

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6.
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    Azolo[5,1-c][1,2,4]triazines and azoloazapurines: synthesis, antimicrobial activity and in silico studies / E. K. Voinkov, R. A. Drokin, V. V. Fedotov [et al.] // ChemistrySelect. - 2022. - Vol. 7, № 5. - Pe202104253
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The present work reports on the synthesis of series of azolo[5,1-c][1,2,4]triazines and derivatives of azoloazapurines. The synthesized compounds were tested in vitro for antibacterial activity against N. gonorrhoeae and antimycotic activity against Trichophyton interdigitale, Epidermophyton floccosum, Microsporum canis and Candida albicans. It was found that 10 compounds of the series of 3-nitroazolo[5,1-c][1,2,4]triazine-4-amines 4 exhibit high antibacterial activity (MIC≤15 μg/ml), but do not exhibit antimycotic activity. For compounds active against N. gonorrhoeae, a biological target was predicted from the pharmacophore search method and homologous modeling was carried out for it. The results of molecular docking using the constructed model of dihydrofolate reductase have a good correlation with in vitro tests. Refined docking showed the similarity of the leading compounds positions in the protein active site. The formation of stable non-covalent bonds of the nitro group with the amino acid residues Lys34/Lys55 makes a major contribution to the orienting effect of ligands.

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7.
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    Coumarin-pyridine push-pull fluorophores: synthesis and photophysical studies / R. F. Fatykhov, A. D. Sharapov, E. S. Starnovskaya [et al.] // Spectrochimica acta part A: molecular and biomolecular spectroscopy. - 2022. - Vol. 267. - Ст. 120499
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A series of coumarin-pyridine-based push-pull fluorophores were prepared starting from 1,2,4-triazines by using direct C-H functionalization (SNH-reaction)–Diels-Alder–retro Diels-Alder domino reaction sequence. This efficient synthetic strategy allowed to obtain a series of 19 coumarin-pyridine fluorophores. Their photophysical properties were studied. While pyridine-substituted derivatives of 4-alkylcoumarins may be considered as alternative to coumarin dyes characterized by emission maxima mainly in a visible region with wavelengths of 402–415 nm, absorption in the UV range at 210–307 nm, and good photoluminescence quantum yields of 6–19%, all the derivatives of 4-phenylcoumarin did not exhibit any noticeable fluorescence. More detailed photophysical studies were carried out for two the most representative derivatives of 4-alkyl-coumarin-pyridines to demonstrate their positive solvatochromism, and the collected data were analyzed by using Lippert-Mataga equation, as well as Kosower and Dimroth/Reichardt scales. The obtained results demonstrate that the combining two chromophore systems, such as 2,5-diarylpyridine and coumarin ones, is promising in terms of improving the photophysical properties of the new coumarin-pyridine hybrid compounds.

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8.
Инвентарный номер: нет.
   
   Z 99

   
    [1,2,4]Triazolo[1,5-d][1,2,4]triazines (microreview) / A. P. Krinochkin, D. S. Kopchuk, G. V. Zyryanov, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 1. - P7-9
УДК
54
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: In this microreview, we cover all currently known methods for the preparation of [1,2,4]triazolo[1,5-d][1,2,4]triazines, involving the assembly of a triazine ring on the basis of a triazole-containing starting material or the assembly of a triazole ring starting from a triazine-containing compound.

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9.
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   M 61

   
    Methods of Synthesis and Antiviral Activity of New 4-Alkyl-3-Nitro-1,4-Dihydroazolo[5,1-c][1,2,4]Triazin-4-ols / R. A. Drokin, D. V. Tiufiakov, E. K. Voinkov [et al.] // Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 4. - P473–478
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
3-NITROAZOLO[5,1-С][1,2,4]TRIAZINES -- a-NITRO KETONES -- TRIAZINES
Аннотация: An azo coupling reaction of α-nitro ketones with 5-diazoazoles was used to obtain 4-alkyl-3-nitro-1,4-dihydroazolo[5,1-с][1,2,4]triazines, which were characterized with respect to their antiviral activity against influenza and Coxsackie B3 viruses.

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10.
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    Asymmetrically functionalized 1,3-Di(2-pyridyl)benzenes: synthesis and photophysical studies / E. S. Starnovskaya, D. S. Kopchuk, Y. K. Shtaitz [et al.] // Journal of fluorescence. - 2021. - № 32. - P125–133
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
1,2,4-TRIAZINES -- 1,3-DI(2-PYRIDYL)BENZENES -- AZA-DIELS-ALDER REACTION -- CROSS-COUPLING -- FLUORESCENCE
Аннотация: A convenient synthetic approach to asymmetrically functionalized 1,3-di(2-pyridyl)benzenes starting from 3-(3-bromophenyl)-1,2,4-triazines using sequential aza-Diels–Alder reactions and Stille cross-coupling is reported. Photophysical properties of the obtained compounds are studied.

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