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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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    Hydrogen-donor properties of the anthracene fraction of coal tar in the reactions of thermal solvolysis / A. P. Krasikova, E. I. Andreykov, Yu. A. Dikovinkina [и др.] // Coal chemistry and ecology of Kuzbass : XII International Russian-Kazakh Symposium. - Kemerovo, 2023. - С. 50
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The reactions of hydrogen transfer from anthracene oil to model organic compounds – hydrogen acceptors are investigated. Solvolysis of thermosetting polymers in anthracene oil has been carried out.

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3.
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    Synthesis of δ-Valerolactone Using Stable Hydrogen Peroxide Derivatives / Y. V. Solovyova, A. V. Pestov, I. S. Puzyrev [et al.] // Russian Journal of Organic Chemistry. - 2022. - Vol. 58, № 4. - P480-483
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The efficiencies of hydrogen peroxide derivatives in the Baeyer–Villiger oxidation of cyclopen­tanone to δ-valerolactone have been compared. The oxidants used were hydrogen peroxide in acetic, formic, or trifluoroacetic acid, magnesium and sodium monoperoxyphthalates, cumene hydroperoxide, and tert-butyl hydroperoxide. The oxidation was carried out in water, aqueous methanol, and water–ethyl acetate. Sodium and magnesium monoperoxyphthalates turned out to provide high conversion and selectivity under mild conditions.

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4.
Инвентарный номер: нет.
   

   
    Investigation of hydrogen transfer from coal tar pitch and petroleum pitches using a-methylstyrene as hydrogen acceptor / E. I. Andreikov, A. P. Krasikova, M. G. Pervova, A. S. Kabak // Chemistry for sustainable development. - 2022. - Vol. 30, № 5. - P446-454
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
A-METHYLSTYRENE -- COAL TAR PITCH -- PETROLEUM PITCHES
Аннотация: The reaction of hydrogen transfer from coal tar pitch and petroleum pitches to Α-methylstyrene with the formation of cumene was investigated in glass ampoules within the temperature range of 200-360 °C and reaction time of 15-60 min and when passing Α-methylstyrene through a layer of coal tar pitch. It is shown that the formation of non-chromatographable products of Α-methylstyrene condensation with polycyclic aromatic compounds of pitches occurs simultaneously. The dependences of Α-methylstyrene conversion, the selectivity for cumene and condensation products on the temperature and reaction time, the ratio of pitch/Α-methylstyrene are determined. The amount of hydrogen transferred from pitches to Α-methylstyrene was determined, and the results obtained were compared with the literature data on the transfer of hydrogen from pitches obtained using anthracene as a hydrogen acceptor.

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5.
Инвентарный номер: нет.
   

   
    Abnormal push-pull benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores in planarized intramolecular charge transfer (PLICT) state: Synthesis, photophysical studies and theoretical calculations / O. S. Taniya, V. V. Fedotov, L. K. Sadieva [et al.] // Dyes and Pigments. - 2022. - Vol. 204. - Ст. 110405
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The combination of excellent luminescence with high solvent polarity effect and aggregation induced emission (AIE) is an ideal combination for creating fluorophores/probes with high microenvironmental sensitivity. However, many push-pull chromophores of the D−A type in common intramolecular charge transfer (ICT) state with a significant solvatochromic effect and AIE activity, have poor luminescent properties. Herein, to overcome this problem by using reactions of nucleophilic aromatic hydrogen substitution (SNH), we have designed a series of novel 4-heteroaryl-substituted 2-aryl-2H-benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores possessing a planarized intramolecular charge transfer (PLICT) state. All these fluorophores exhibited high luminescence quantum yields (up to 60%) and large Stokes shift values of up to 7459 cm−1. Among them, the fluorophore 4h was found to exhibit the most pronounced positive solvatochromic effect and the probe 4f exhibited the most pronounced aggregation induced emission characteristics. This AIE behavior was further confirmed by means of time-resolved fluorescence lifetime measurements as well as DFT-assisted geometry optimization studies. In the presence of trifluoroacetic acid (TFA) compound 4h exhibited a well-pronounced acidochromism via visible color change from yellow-green to orange which returned to the original yellow-green solution after the addition of triethylamine (TEA). The Stern-Volmer constant for the probe 4h towards TFA was 38 M−1. Finally, for the compounds 4f, g, h theoretical calculations in the ground and excited states in different solvents were carried out to confirm the PLICT process. Based on all above the herein reported PLICT fluorophores 4a-h can be successfully applied as biological probes and optical switches.

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6.
Инвентарный номер: нет.
   

   
    Synthesis and physicochemical properties of nanostructured TiO2 with enhanced photocatalytic activity / I. B. Dorosheva, A. A. Valeeva, A. A. Rempel [et al.] // Inorganic Materials. - 2021. - Vol. 57, № 5. - P503-510
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
TITANIUM DIOXIDE -- SOL–GEL METHOD -- PHOTOCATALYSIS
Аннотация: Nanostructured titanium dioxide (TiO2) with a crystallite size from 10 to 85 nm, photocatalytically active for organic reactions under illumination with visible light, has been prepared by a sol–gel process using a titanium tetrabutoxide solution in ethanol with an initial pH of 6. According to X-ray diffraction characterization results, the as-prepared titanium dioxide was amorphous. Annealing in a hydrogen atmosphere for 1 h at 400°C led to the formation of an anatase phase, and annealing in the temperature range from 600 to 800°C resulted in the anatase–rutile phase transition. The crystallite size of titanium dioxide increased from 10 to 75 nm as the annealing temperature was raised from 400 to 1000°C (furnace annealing for 1 h) and from 60 to 85 nm as the annealing time at a temperature of 800°C was increased from 30 to 240 min. Diffuse reflection spectra showed that the band gap of TiO2 decreased from 3.3 to 2.6 eV as the annealing temperature was raised from 200 to 1000°C. The specific surface area data obtained by BET measurements showed that the samples annealed at the highest temperature (1000°C) had the smallest surface area, which dropped from 307 to 1m2/g. The efficiency of the synthesized TiO2 tested as a catalyst for oxidative S H N cross-coupling of acridine with indole demonstrated an in crease in product yield from 35 to 80% as the annealing temperature was raised to 800°C. Varying the 800°C annealing time from 30 to 180 min had no effect on the reaction product yield, which ranged from 70 to 80%.

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7.
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    Synthesis, fungicidal activity, and molecular docking of 2-acylamino and 2-thioacylamino derivatives of 1 H-benzo[ d]imidazoles as anti-tubulin agents / K. L. Obydennov, T. A. Kalinina, N. A. Galieva [et al.] // Journal of agricultural and food chemistry. - 2021. - Vol. 69, № 40. - P12048-12062
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
BENZIMIDAZOLES -- ANTIFUNGAL ACTIVITY -- TUBULIN -- CARBENDAZIM
Аннотация: This work deals with the synthesis and evaluation of fungicidal activity of benzimidazole derivatives, which are structural analogues of commercial anti-tubulin fungicides. A number of N-acyl and N-thioacyl derivatives of 2-amino-1H-benzo[d]imidazole were prepared, and their fungicidal activity against 13 strains of phytopathogenic fungi was studied. The most active compounds against the majority of the studied strains were 3a, 4l, and 4o, and the EC50 values of these compounds were in the range 2.5–20 μg/mL. Compound 3a showed the highest activity against the P. infestans strain, the growth of which is not suppressed by carbendazim. The formation of ligand–receptor complexes of various tautomeric forms of the studied benzimidazoles with homologous models of β-tubulins of B. cinerea, F. oxysporum, and P. infestans was modeled. Induced fit docking has been used for the simulation. The obtained data suggest the possibility of binding of benzimidazole fungicides to β-tubulin in the ″nocodazole cavity″ in the tautomeric form bearing a double exocyclic C═N bond. The importance of the formation of hydrogen bonds of benzimidazoles with the amino acid residue Val236 along with the Glu198 residue is also revealed in the present study.

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8.
Инвентарный номер: нет.
   
   D 46

   
    Design and antioxidant properties of bifunctional 2H-imidazole-derived phenolic compounds-a new family of effective inhibitors for oxidative stress-associated destructive processes / E. L. Gerasimova, E. R. Gazizullina, M. V. Borisova [et al.] // Molecules. - 2021. - Vol. 26, № 21. - Ст. 6534
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
2H-IMIDAZOLE -- POLYPHENOLS -- ANTIOXIDANT CAPACITY -- ANTIRADICAL CAPACITY
Аннотация: The synthesis of inhibitors for oxidative stress-associated destructive processes based on 2H-imidazole-derived phenolic compounds affording the bifunctional 2H-imidazole-derived phenolic compounds in good-to-excellent yields was reported. In particular, a series of bifunctional organic molecules of the 5-aryl-2H-imidazole family of various architectures bearing both electron-donating and electron-withdrawing substituents in the aryl fragment along with the different arrangements of the hydroxy groups in the polyphenol moiety, namely derivatives of phloroglucinol, pyrogallol, hydroxyquinol, including previously unknown water-soluble molecules, were studied. The structural and antioxidant properties of these bifunctional 5-aryl-2H-imidazoles were comprehensively studied. The redox transformations of the synthesized compounds were carried out. The integrated approach based on single and mixed mechanisms of antioxidant action, namely the AOC, ARC, Folin, and DPPH assays, were applied to estimate antioxidant activities. The relationship “structure-antioxidant properties” was established for each of the antioxidant action mechanisms. The conjugation effect was shown to result in a decrease in the mobility of the hydrogen atom, thus complicating the process of electron transfer in nearly all cases. On the contrary, the conjugation in imidazolyl substituted phloroglucinols was found to enhance their activity through the hydrogen transfer mechanism. Imidazole-derived polyphenolic compounds bearing the most electron-withdrawing functionality, namely the nitro group, were established to possess the higher values for both antioxidant and antiradical capacities. It was demonstrated that in the case of phloroglucinol derivatives, the conjugation effect resulted in a significant increase in the antiradical capacity (ARC) for a whole family of the considered 2H-imidazole-derived phenolic compounds in comparison with the corresponding unsubstituted phenols. Particularly, conjugation of the polyphenolic subunit with 2,2-dimethyl-5-(4-nitrophenyl)-2H-imidazol-4-yl fragment was shown to increase ARC from 2.26 to 5.16 (104 mol-eq/L). This means that the considered family of compounds is capable of exhibiting an antioxidant activity via transferring a hydrogen atom, exceeding the activity of known natural polyphenolic compounds.

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9.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis of novel 3-(pyridin-4-yl)-1,2,4-triazines, their analogs and study of the activity against vaccinia virus / O. V. Shabunina, Y. K. Shtaitz, D. S. Kopchuk [et al.] // Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 4. - P462–466
УДК
Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
1,2,4-TRIAZINES -- ANTIVIRAL ACTIVITY -- IPSO SUBSTITUTION -- NUCLEOPHILIC HYDROGEN SUBSTITUTION
Аннотация: Using atom-economical approaches, new representatives of 3-(pyridin-4-yl)-1,2,4-triazines and their 4-nitrophenyl analogs were obtained, and their activity in relation to the vaccinia virus was studied. The new compounds have shown promising characteristics, in particular, in comparison to the antiviral drug Cidofovir.

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10.
Инвентарный номер: нет.
   
   B 68

   
    Blue-light-promoted radical c-h azolation of cyclic nitrones enabled by selectfluor® / A. A. Akulov, M. V. Varaksin, A. N. Tsmokalyuk [et al.] // Green Chemistry. - 2021. - Vol. 23, № 5. - P2049-2057
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: An original approach to achieve the C(sp2)–H azolation of cyclic aldonitrones mediated by Selectfluor® has first been employed. By exploiting a metal-free, visible-light-promoted cross-dehydrogenative C–N coupling reaction between model aldonitrones, 2H-imidazole 1-oxides, and NH-containing azoles, a series of novel azaheterocyclic derivatives have been obtained in yields up to 94%. The elaborated protocol has proved to be appropriate for gram-scale processes and displayed potential for utilization in the synthesis of novel structural analogues of lanabecestat. Besides, mechanistic studies have revealed that this coupling reaction is likely to proceed via a nitroxide-involving radical pathway, encompassing a chain of electron transfer events, such as hydrogen atom transfer (HAT) and single electron transfer (SET).

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