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卷 60, 编号 6 (2024)

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Articles

Nucleophilic functionalization of tropilium salts with heterocyclic amines, amides or hydrazides of carboxylic acids

Yunnikova L., Pshenitsyna O.

摘要

The review summarizes the results on new reactions of nucleophilic functionalization of tropylium salts with heterocyclic amines, amides or hydrazides of monocarboxylic acids over the past 10 years.

Žurnal organičeskoj himii. 2024;60(6):6-22
pages 6-22 views

On the mechanism of intramolecular cyclization of quaternary ammonium salts containing, along with β,γ-unsaturated groups, various π4-fragments

Gevorgyan A., Chukhadzhyan E., Hayrapetyan L.

摘要

The review examines the mechanism of intramolecular cyclization, similar to the diene synthesis of quaternary ammonium salts containing, along with β,γ-unsaturated groups, various enyne fragments.

Žurnal organičeskoj himii. 2024;60(6):23-37
pages 23-37 views

Synthesis, spectral, electrochemical properties, antioxidant and antiviral activity of new 2-[5-phenyl-6-methyl-3-aryl/getaryl-5,6-dihydro-4h-[1,2,4,5]tetrazine-1-yl]-benzothiazoles

Fedorchenko T., Lipunova G., Volobueva A., Zarubaev V., Valova M., Shchepochkin A., Averkov M., Tungusov V., Slepukhin P., Chupakhin O.

摘要

New 2-[5-aryl-6-methyl-3-aryl/getaryl-5,6-dihydro-4H-[1,2,4,5]tetrazine-1-yl]-benzothiazole has been synthesized from the corresponding formazanes by alkylation and subsequent cyclization of N-alkyl derivatives. The products are characterized by 1H, 13C NMR, IR, spectroscopy, mass spectrometry and X-ray diffraction analysis. The electrochemical properties, antioxidant and antiviral activity of the obtained benzothiazoles were studied.

Žurnal organičeskoj himii. 2024;60(6):38-50
pages 38-50 views

Alkenylation of hydroxy derivatives of adamantane with alcohols in the presence of sulfuric acid

Baimuratov M., Aristova U., Shishkina M., Leonova M., Klimochkin Y.

摘要

A series of adamantyl-containing alkenes was synthesized by alkenylation of 1-adamantanol with secondary alcohols in the presence of sulfuric acid. The boundaries of this reaction are shown, and it is revealed that in the case of using symmetrical dialkylcarbinols, alkenylation occurs selectively. When 1-adamantanol is alkenylated with sec-amyl alcohol and higher homologues, the formation of mixtures of isomeric alkenes is observed. The reactions of substituted adamantanols with isopropanol, 2-butanol and cyclohexanol in the presence of sulfuric acid were studied, and a series of new unsaturated derivatives of the adamantane series were obtained.

Žurnal organičeskoj himii. 2024;60(6):51-61
pages 51-61 views

Synthesis and conversions of benzo-substituted 1-[2-methyl4-(methyltio)quinolin-3-yl]propan-2-ones

Aleksanyan I., Hambardzumyan L.

摘要

New derivatives of Schiff bases were synthesized using 1-[2-methyl-4-mercaptoquinolin-3-yl]propan-2-ones and 1-[2-methyl-4-(methylthio)quinoline substituted in the benzene ring-3- yl]propan-2-ones as starting materials. To obtain the 4-methylthio derivatives of the Schiff base, the corresponding 4-mercaptoquinoline-propan-2-ones and 3-(2-chloroallyl)-4-mercaptoquinolines were first methylated, followed by acid hydrolysis of the chloro allyl group in the latter samples.

Žurnal organičeskoj himii. 2024;60(6):62-68
pages 62-68 views

Synthesis, structure and reactions of substituted 2-aminotetrahydrochynoline-3-carbonitriles

Nikulin A., Vasilkova N., Krivenko A.

摘要

A series of substituted 2-aminotetrahydroquinolinecarbonitriles was obtained by three-component condensation of diaryl(hetaryl)methylidenecyclohexanones, malononitrile and ammonium acetate. Factors influencing the selectivity of reactions and the route of product formation have been identified. The interaction of aminoquinoline carbonitriles with acetic anhydride under acid catalysis conditions led to the formation of substituted hexahydropyrimido[4,5-b]quinolinones. The structure of the compounds was established using IR, 1H, 13C NMR spectra and two-dimensional correlations HSQC spectroscopy.

Žurnal organičeskoj himii. 2024;60(6):69-77
pages 69-77 views

Synthesis, photophysical and electrochemical properties of conjugated d-a-d systems based on 1,3,4-thiadiazoles and fused naphtho[2,1-b]thiophene derivatives

Uliankin E., Kostyuchenko A., Fisyuk A.

摘要

A series of 2,5-diaryl substituted 1,3,4-thiadiazoles was obtained based on fused benzothiophene-2-carboxylates and alkyl substituted 2,2’-bithiophene-5-carboxylates. The photophysical and electrochemical properties of these compounds were studied and it was determined that an increase in the conjunction chain in the donor fragment of the substituted 1,3,4-thiadiazole leads to narrowing of the band gap mainly due to an increase in the HOMO level.

Žurnal organičeskoj himii. 2024;60(6):78-87
pages 78-87 views

Synthesis and influence of new indole-containing benzo[f]coumarin derivatives on proliferation and redox state of rat glioma cells line c6

Kulahava T., Shumski V., Mineyeva I.

摘要

For the first time, modification of 2-acetyl-3H-benzo[f]chromen-3-one and 2-[(2E)-3-phenylprop-2-enoyl]-3H-benzo[f]chromen-3-one was carried out due to interaction with indole. It has been established that the resulting benzo[f]coumarin derivatives exhibit antioxidant properties in model systems — they interact with hydrogen peroxide, sodium hypochlorite and regulate the redox state of rat glioma cells line C6, which is manifested by a decrease in the concentration of intracellular hydrogen peroxide and an increase in the level of reduced glutathione. In the presence of exogenous hydrogen peroxide, synthesized benzo[f]coumarin compounds have a protective effect on cells, acting as antioxidants and restoring redox balance. It was found that 2-[3-(1H-indol-3-yl)-3-phenylpropanoyl]-3H-benzo[f]chromen-3-one in micromolar concentrations inhibits the proliferative activity of C6 rat glioma cells by 25–35%.

Žurnal organičeskoj himii. 2024;60(6):88-100
pages 88-100 views

Synthesis of bi- and polycyclic pyrimidine derivatives

Sokolnikova T., Proidakov A., Penzik M., Kizhnyaev V.

摘要

Based on the modification of the Biginelli reaction, various bi- and polycyclic pyrimidine derivatives (including the condensed series) were synthesized and identified, in the structure of which there are aza- and carbocyclic fragments of various nature.

Žurnal organičeskoj himii. 2024;60(6):101-110
pages 101-110 views