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 Найдено в других БД:Каталог книг и продолжающихся изданий (10)Каталог препринтов УрО РАН (1975 г. - ) (1)Труды Института высокотемпературной электрохимии УрО РАН (5)Труды сотрудников Института теплофизики УрО РАН (2)Труды сотрудников Института химии твердого тела УрО РАН (46)Расплавы (1)Публикации Черешнева В.А. (2)Публикации Чарушина В.Н. (58)Каталог библиотеки ИЭРиЖ УрО РАН (5)
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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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    Mechanochemical synthesis of coumarins via Pechmann condensation under solvent-free conditions: an easy access to coumarins and annulated pyrano[2,3-f] and [3,2-f]indoles / A. D. Sharapov, R. F. Fatykhov, I. A. Khalymbadzha [и др.] // Green Chemistry. - 2022. - Vol. 24, № 6. - P2429-2437
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
A green protocol has been developed for the synthesis of simple coumarins and linear pyrano[2,3-f] and [3,2-f]indoles by the reaction of phenol derivatives with β-ketoesters under ball milling at ambient temperature in the presence of methanesulfonic acid as a mild acid catalyst. The significant advantages of this procedure are high yields, scalability, no use of hazardous acids or solvents, shorter reaction time, ambient temperature, low cost, and straightforward purification without column chromatography. This procedure is associated with high EcoScale metrics and a low E-factor. In contrast to traditional Pechmann condensation procedures, the mechanochemical protocol leads to the synthesis of pyranoindoles with excellent regioselectivity and high yields.

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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.
   

   
    Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (R)-2-phenoxypropanoate / D. A. Gruzdev, S. A. Vakarov, M. A. Korolyova [et al.] // Organic & biomolecular chemistry. - 2022. - Vol. 20, № 4. - P862-869
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The diastereoselective acylation of a number of racemic methyl-substituted cyclic alkylamines with active esters of 2-phenoxypropanoic acid was studied in detail. The ester of (R)-2-phenoxypropanoic acid and N-hydroxysuccinimide was found to be the most selective agent. The highest stereoselectivity was observed in the kinetic resolution of racemic 2-methylpiperidine in toluene at −40 °C (selectivity factor s = 73) with the predominant formation of (R,R)-amide (93.7% de). To explain the observed stereoselectivity, DFT modelling of the transition states in the reactions of the title acylating agent with 2-methylpiperidine and 2-methylpyrrolidine was performed. The calculated values were in good agreement with experimental data. It has been demonstrated that the acylation proceeds via a concerted mechanism, in which the addition of an amine occurs simultaneously with the elimination of the hydroxysuccinimide fragment. The high stereoselectivity of the (R,R)-amide formation is largely ensured by the lower steric hindrances in the transition states as compared to the formation of (R,S)-amide.

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5.
Инвентарный номер: нет.
   

   
    Opening of the 1,3,5-triazine ring in 3-methyl-5-(trinitromethyl)tetrazolo[1,5-a][1,3,5]triazin-7-one by the action of alcohols / V. V. Bakharev, A. A. Gidaspov, V. A. Zalomlenkov [et al.] // Chemistry of Heterocyclic Compounds. - 2022. - Vol. 58. - P153–158
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: It was shown for the first time that in the reaction of 3-methyl-5-(trinitromethyl)tetrazolo[1,5-a][1,3,5]triazin-7-one with alcohols in the presence of bases, along with the expected substitution of the trinitromethyl group, opening of the 1,3,5-triazine ring with the addition of an alcohol at the site of the C–N bond cleavage takes place. It was found that in the absence of bases only opening of the 1,3,5-triazine ring occurs with the formation of alkyl esters of {1-[(1-methyl-1H-tetrazol-5-yl)imino]-2,2,2-trinitroethyl}carbamic acid, and the trinitromethyl group retains high reactivity and can be substituted by the action of alcohols in the presence of a base.

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6.
Инвентарный номер: нет.
   

   
    Combined approach to conformational analysis of 4-hydroxyproline containing podands using NMR and molecular dynamics simulation / G. Makarov, O. Borodina, A. E. Masunov [et al.] // AIP conference proceedings. - 2022. - Vol. 2390. - Ст. 020045
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
METADYNAMICS -- POLYMERS -- AMINO ACID
Аннотация: Conformational analysis of (2S,4R)-4-hydroxyproline-containing podand based on bias-exchange well-tempered metadynamics computation was performed, and the most representative conformers were selected from generated manifold of conformations by two approaches: by direct clustering by GROMOS algorithm and by partitioning conformations according to torsion angles of polyether chain and free energies of conformers.

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7.
Инвентарный номер: нет.
   

   
    Polyfluorosalicylic acids as ligands for the creation of bioactive metal complexes / E. V. Shchegolkov, I. V. Shchur, Y. V. Burgart, V. I. Saloutin // AIP conference proceedings. - 2022. - Vol. 2390. - Ст. 020076
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
LIGANDS
Аннотация: The reactions of copper(II) and cobalt(II) mixed complexes based on methyl trifluorosalicylate and 2,2’-bipyridine and 1,10-phenanthroline with 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) as the Lewis acid were investigated. In the case of copper(II) complexes, the hydrolysis of ester fragment occurred to form heteroligand complexes of trifluorosalicylic acid and bipyridine-like ligand associated with fluorinated alcohol. The structure of complexes corresponded to [Cu(L3-H2)(bipy or phen)*(HFIP), L3 −trifluorosalicylic acid]. In contrast, cobalt(II) complexes in refluxing HFIP resulted in the complexes [Co(L1-H)2(bipy or phen)*(HFIP), L1 – methyl trifluorosalicylate], in which the ester ligand was preserved.

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8.
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    Expanding 1,2,4-triketone toolbox for use as fluorinated building blocks in the synthesis of pyrazoles, pyridazinones and β-diketohydrazones / Y. O. Edilova, Y. V. Burgart, V. I. Saloutin [et al.] // Journal of fluorine chemistry. - 2022. - Vol. 253. - Ст. 109932
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Fluorinated lithium β-diketonates bearing a methyl acetal group behave in the condensation reactions with hydrazines as trielectrophilic building blocks for the preparation of pyrazoles, pyridazinones and β-diketohydrazones. For the first time, solvent-induced regioisomeric and heterocyclic ring size-controlled formation was observed for 1,2,4-triketone analogues. Fluoroalkylated acetyl NH-pyrazoles or substituted 5-RF-pyrazoles were obtained from the acid-catalyzed cyclocondensation of lithium β-diketonates with (aryl)hydrazines in ethanol. In methanol solvent acetyl-containing 3-CF3-pyrazoles were isolated because of inverse nucleophilic attack of arylhydrazines. The use of aprotic acetonitrile in the condensation resulted in regioselective trifluorinated pyridazinones and fluorinated β-diketohydrazones formation via initial acetal fragment interaction with N,N-dinucleophile.

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9.
Инвентарный номер: нет.
   

   
    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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10.
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    Chitosan cross-linking with acetaldehyde acetals / A. Pestov, Y. Privar, A. Slobodyuk [et al.] // Biomimetics. - 2022. - Vol. 7, № 1. - Ст. 10
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CHITOSAN -- ACETALDEHYDE ACETALS -- HYDROGEL
Аннотация: Here we demonstrate the possibility of using acyclic diethylacetal of acetaldehyde (ADA) with low cytotoxicity for the fabrication of hydrogels via Schiff bases formation between chitosan and acetaldehyde generated in situ from acetals in chitosan acetate solution. This approach is more convenient than a direct reaction between chitosan and acetaldehyde due to the better commercial availability and higher boiling point of the acetals. Rheological data confirmed the formation of intermolecular bonds in chitosan solution after the addition of acetaldehyde diethyl acetal at an equimolar NH2: acetal ratio. The chemical structure of the reaction products was determined using elemental analysis and 13C NMR and FT-IR spectroscopy. The formed chitosan-acetylimine underwent further irreversible redox transformations yielding a mechanically stable hydrogel insoluble in a broad pH range. The reported reaction is an example of when an inappropriate selection of acid type for chitosan dissolution prevents hydrogel formation.

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