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Volume 61, Nº 3 (2025)
ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
Synthesis and properties of 1,3-disubstituted ureas and its isostering analogs containing polycyclic fragments: XIX. Exo-isomers of 1-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-3-R ureas and thioureas
Resumo
For a comprehensive assessment of the enantiomeric stereospecificity of human soluble epoxide hydrolase (hsEH), 1,3-disubstituted ureas and thioureas containing a bornyl fragment in their structure were synthesized according to the reaction exo-(R or S)-1,1,7-trimethylbicyclo[2.2.1]heptane-2-amine with aromatic isocyanates and isothiocyanates with yields up to 99%. Synthesized compounds are promising inhibitors of hsEH.
Russian Journal of Organic Chemistry. 2025;61(3):221-229
221-229
Formation of 1-(2,4,6-trifluorophenyl)perfluorobenzocyclobutene from perfluorobenzocyclobutene and 1,3,5-trifluorobenzene and its interaction with polyfluorobenzenes in an SBF5 medium
Resumo
Interaction of perfluorobenzocyclobutene with two equivalents of 1,3,5-trifluorobenzene in an SbF5 medium followed by the treatment of the reaction mixture with water gave (3,4,5,6-tetrafluorobenzene-1,2-diyl)bis[(2,4,6-trifluorophenyl)methanone], 1-(2,4,6-trifluorophenyl)perfluorobenzocyclobuten-1-ol and 4,5,6,7-tetrafluoro-1,3,3-tris(2,4,6-trifluorophenyl)-1,3-dihydro-2-benzofuran-1-ol. When the reaction mixture was treated with HF, 1,2-bis(2,4,6-trifluorophenyl)-perfluorobenzocyclobutene along with 1-(2,4,6-trifluorophenyl)perfluorobenzocyclobutene were obtained. The latter compound reacted with pentafluoro-, 1,2,3,4- or 1,2,4,5-tetrafluorobenzenes in an SbF5 medium to give corresponding polyfluoro-1,2-diphenylbenzocyclobutenes after treatment of the reaction mixture with HF.
Russian Journal of Organic Chemistry. 2025;61(3):230-239
230-239
1H-1,2,4-Triazolo-5-diazonium salts in the synthesis of new 6H-benzopyrano[4,3-e][1,2,4]triazolo[5,1-c]-[1,2,4]triazine-6-ones and [1,2,4]triazolo[5',1':3,4][1,2,4]-triazino[6,5-c]quinoline-6(7H)-ones
Resumo
A convenient synthetic approach to the synthesis of new 2-R-6Н-benzopyrano[4,3-е][1,2,4]triazolo[5,1-с][1,2,4]triazin-6-ones and 2-R-[1,2,4]triazolo[5',1':3,4][1,2,4]triazino[6,5-c]quinolin-6(7H)-ones based on 3-R-1H-1,2,4-triazolo-5-diazonium salts with 2H-1-benzopyran-2,4(3H)dione and 2,4(1H,3H)-quinolinedione.
Russian Journal of Organic Chemistry. 2025;61(3):240-245
240-245
246-252
Synthesis, antimicrobial and analgesic activity of 5-(Get)aryl-4-(trifluoromethyl)furan-2,3-diones recycling products under the action of aromatic amines
Resumo
As a result of the reaction of 5-substituted 4,4,4-trifluoroacetylfuran-2,3-diones with aromatic amines, 4-substituted 5-hydroxy-5-(trifluoromethyl)dihydrofuran-2,3-diones, were synthesized, which have antibacterial and antinociceptive activities.
Russian Journal of Organic Chemistry. 2025;61(3):253-263
253-263
SYNTHESIS OF POLYCARBOXYLIC DIAMANTHYLATED ARENES
Resumo
Double alkylation reactions of aromatic hydrocarbons with carboxylic acids and hydroxy-substituted mono- and dicarboxylic acids in acidic media have been carried out. The obtained polycarboxylic diadamantylated arenes can be considered as a new type of structurally rigid polycarboxylate ligands in the directed design of metal-organic coordination frameworks.
Russian Journal of Organic Chemistry. 2025;61(3):264-273
264-273
Synthesis of new derivatives of 18-membered macrocycles by cyclocondensation of pyrazole series hydrazine hydrazides
Resumo
Studies on the synthesis of new representatives of 18-membered nitrogenous macrogeterocycles of the biacylhydrazone type based on N-phenacyl- and N-carbalkoxymethylpyrazoles having a carboxyalkyl or acetyl group in the ring carbon atoms were conducted.
Russian Journal of Organic Chemistry. 2025;61(3):274-284
274-284
Synthesis and transformations of O-propargyl analogues of fusidic acid
Resumo
In continuation of the studies on synthetic modifications of fusidane triterpenoids, an O-propargyl fragment was introduced at the C3 atom of the fusidic acid methyl ester molecule and chemical transformations of the triple bond were carried out through reactions catalyzed by copper(I) salts to obtain an aminomethylene analogue, 1,2,3-triazole, and an aryl-substituted acetylene derivative.
Russian Journal of Organic Chemistry. 2025;61(3):285-292
285-292
SYNTHESIS, SYMPATHOLYTIC AND ADRENOLYTIC ACTIVITY OF AMINOAMIDES AND AMINОESTERS ON THE BASE OF 1-(BENZO[D][1,3]DIOXOL-5-YL)-CYCLOPENTANE- AND 4-(BENZO[D][1,3]DIOXOL-5-YL)TETRAHYDRO- 2H-PYRANE-4-CARBOXYLIC ACIDS
Resumo
By the reaction of 2-(benzo[d][1,3]dioxol-5-yl)acetonitrile with dibromobutane and 2,2'-dichlorodiethyl ether, nitriles of 1-(benzo[d][1,3]dioxol-5-yl)cyclopentane- and 4-(benzo[d][1,3]dioxol-5-yl)tetrahydro-2H-pyran-4-carboxylic acids were synthesized, converted into the corresponding acids by alkaline hydrolysis. Targeted (benzo[d][1,3]dioxol-5-yl)cyclopentane(tetrahydropyran)-carboxamides and (benzo[d][1,3]dioxol-5-yl)cyclopentane(tetrahydropyran)-carboxylates were synthesized by interaction of acid chlorides of isolated acids with N,N-dialkylaminoalkyl- and heterylalkylamines, as well as with N,N-dialkylaminoalkyl- and heterylalkylalcohols. The effect of the synthesized compounds on the cardiovascular system and blood hemodynamics was studied.
Russian Journal of Organic Chemistry. 2025;61(3):293-301
293-301
SYNTHESIS OF QUINOLYL SUBSTITUTED THIAZOLIDINES AND DIHYDROTHIAZOLES BASED ON 2-{1-[2-METHYL-4-(METHYLTHIO)-QUINOLIN-3-YL]PROPAN-2-YLIDENE}HYDRAZINOCARBOTHIOAMIDES SUBSTITUTED IN THE BENZENE RING
Resumo
The diverse biological activity of heterocyclic compounds makes them one of the most important areas of pharmaceuticals and organic synthesis. In this work, a synthesis of new hetarylquinolines containing thiazolidine and dihydrothiazole rings was carried out on the basis of 2-{1-[2-methyl-4-(methylthio)-quinolin-3-yl]propan-2-ylidene}hydrazinocarbothioamides substituted in the benzene ring. The synthesis was conducted using readily available and non-toxic starting materials, ensuring a practical and accessible methodology. The results of this work may serve as a foundation for further studies aimed at exploring the biological and applied potential of these compounds.
Russian Journal of Organic Chemistry. 2025;61(3):302-307
302-307
Synthesis of Hexa-Substituted Benzene Derivative Based on 4-Pyridinecarboxaldehyde and Malononitrile
Resumo
The present work reports the synthesis of a new compound 2-amino-4,6-di(pyridin-4-yl)benzene-1.3.5-tricarbonitrile as a result of the reaction of two moles of 2-(pyridin-4-ylmethylene)malononitrile with one mole of malononitrile in the presence of methylpiperazine as a catalyst. The structure of the obtained product was confirmed by NMR and X-ray. A plausible reaction mechanism is presented.
Russian Journal of Organic Chemistry. 2025;61(3):308-312
308-312
Conformational Preference of Oxybis(methylene-1,3-dioxane-5,5-diil)dimethanol in Solvents of Various Nature
Resumo
The conformational preference of oxybis(methylene-1,3-dioxane-5,5-diyl)dimethanol in various solvents was studied by NMR. According to the data of two-dimensional spectroscopy (NOESY), the bis(chair) form with diaxial oxymethyl groups is dominated in С6D6 and CDCl3, while the form with axial and equatorial oxymethyl groups at С5 and С5' atoms of the ring is dominated in DMSO-d6 and CD3CN solvents. The results of computer simulation of the conformational transformation of molecules of the studied diformal within the DFT approximation PBE/def2-SVP in these solvents (cluster model) are in complete agreement with the NMR results. It is shown that the optimal number of solvent molecules in the nearest solvate shell of the studied diformal varies from five to seven depending on the nature of solvent.
Russian Journal of Organic Chemistry. 2025;61(3):313-321
313-321
Cyclization of ethyl [cyano(4,6-dimethylpyrimidin-2-yl)amino]-acetate
Resumo
Imidazolin-4-one derivatives have been prepared by a reaction of ethyl [cyano(4,6-dimethylpyrimidin-2-yl)amino]acetate (2) with morpholine, piperidine and hydrazides. In the presence of sulfuric acid, cyanoester 2 gives 2-iminooxazolin-5-one which is acylated on the nitrogen atom of imino group and is rearranged to imidzolidin-2,4-dione in the presence of KCNO.
Russian Journal of Organic Chemistry. 2025;61(3):322-328
322-328
Spiroheterocyclization of 1-Antipyryl-4-aroyl-5-methoxycarbonyl-1h-pyrrole-2,3-diones under the Action of Dimedone
Resumo
The interaction of 1-antipyryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones with dimedone (5,5-dimethylcyclohexanedione-1,3) leads to the formation of 1'-antipyryl-3'-aroyl-4' -hydroxy-6,6-dimethyl-6,7-dihydro-spiro[benzofuran-3,2'-pyrrole]-2,4,5'(1'H, 5H)-triones. Synthesized compounds of interest for pharmacology and medicinal chemistry.
Russian Journal of Organic Chemistry. 2025;61(3):329-332
329-332
КРАТКОЕ СООБЩЕНИЕ
REACTION OF 2-AMINOBENZOIMIDAZOLES WITH ACETYLENE IN THE KOBUT/DMSO SYSTEM: SELF-ORGANIZATION OF BENZO[D]-IMIDAZO[1,2-A]IMIDAZOLES AND BENZO[4,5]IMIDAZO[1,2-A]-PYRIMIDINES BY THE COMPETITION OF NUCLEOPHILIC CENTERS
Resumo
2-Aminobenzoimidazoles react with acetylene in the KOBut/DMSO superbase system (80°С, 20 min) to give benzoimidazo[1,2-a]imidazoles and benzoimidazo[1,2-a]pyrimidines, the products of self-organization of starting compounds with two or three molecules of acetylene. Moreover, vinyl derivatives of 1,3-dihydro-2H-benzo[d]imidazole-2-imine were obtained.
Russian Journal of Organic Chemistry. 2025;61(3):333-337
333-337
SYNTHESIS OF 2,6-BIS(1H-IMIDAZOLE-2-YL)-4-CHLOROPYRIDINE
Resumo
On the basis of helidamic acid, 4-chloropyridine-2,6-dicarboxamide and 4-chloropyridine-2,6-dicarbonitrile were synthesized sequentially, the interaction of which with diethyl acetal aminoacetaldehyde led to 2,6-bis(1H-imidazole-2-yl)-4-chloropyridine, a tridentate ligand.
Russian Journal of Organic Chemistry. 2025;61(3):338-340
338-340
Method of regeneration of DMSO-d6
Resumo
A method for regenerating DMSO-d6 is proposed, based on the azeotropic distillation of water and volatile impurities with carbon tetrachloride and subsequent removal of impurities distilled from DMSO-d6 by complexation with copper ions.
Russian Journal of Organic Chemistry. 2025;61(3):341-344
341-344