Russian Journal of Organic Chemistry
ISSN (print): 0514-7492
Media registration certificate: No. FS 77 - 67135 dated 09/16/2016
Founder: Russian Academy of Sciences
Editor-in-Chief: Beletskaya Irina Petrovna
Number of issues per year: 12
Indexation: RISC, list of Higher Attestation Commissions, CrossRef, White List (level 3)
Russian Journal of Organic Chemistry is an international peer-reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis. The journal welcomes manuscripts from all countries.
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Volume 61, Nº 6 (2025)
ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
Design, Synthesis, and in vitro Antiproliferative Activity of 4,5,6-Trisubstituted 2-Aminopyrimidines as Potential TGF-β Inhibitors
Resumo
The TGF-β signaling cascade is a regulator of cellular processes such as growth, division, differentiation, migration, invasion and apoptosis. Due to the deep involvement of this signaling pathway in the processes of carcinogenesis, participants in the cascade are promising oncology targets. Based on literature data, we have proposed a new structural class of TGF-β receptor inhibitors based on 2-aminopyrimidines. Two universal approaches to their synthesis have been proposed; the key transformation is the three-component Biginelli condensation aimed at the formation of a pyrimidine fragment. Using the developed synthetic approaches, 16 new compounds were obtained, for which antiproliferative activity in vitro was established against a number of tumor cell lines.
Russian Journal of Organic Chemistry. 2025;61(6):649-661
649-661
Three-Component Synthesis of Tetrahydroisoquinolines Based on the SNVin Reaction
Resumo
A three-component reaction of carbocyclic enaminoketones, CH-acids, and electrophiles was studied. Based on the reaction of nucleophilic vinyl substitution (SNVin), previously unknown derivatives of 5,6,7,8-tetrahydroisoquinolines were synthesized. The structure of a number of products was studied by X-ray diffraction.
Russian Journal of Organic Chemistry. 2025;61(6):662-673
662-673
Synthesis of 3-Substituted 1-dichloromethyladamantanes
Resumo
The transformations of dichloromethyladamantane and its derivatives in strongly acidic media have been studied. It has been established that the nitroxylation reaction is not accompanied by nitrolysis of the dichloromethyl group. A number of products of substitution of dichloromethyladamantane at the 3rd position were obtained under the conditions of generating a tertiary carbenium cation and it was found that the dichloromethyl group was retained in the structure of all products, which allows their further modification.
Russian Journal of Organic Chemistry. 2025;61(6):674-681
674-681
Synthesis of Functionally Substituted 4H-Thiopranes Based on the Reaction of Carbon Disulphide with Malononitrile Trimer
Resumo
Potassium 2-(1-cyano-2,2-disulfidovinyl)-1,1,3,3-tetracyanopropenide was synthesized for the first time by reaction of carbon disulfide with malononitrile trimer. Based on the resulting disulfide, further transformations were carried out, resulting in the production of 2-amino-4-(dicyanonethylene)-4H-thiopyran-3,5-dicarbonitrile derivatives.
Russian Journal of Organic Chemistry. 2025;61(6):682-686
682-686
Mass-Spectra of New Heterocycles: XXIX. Study of 2-(Alkylsulfanyl)quinolines by Electron Ionization
Resumo
The properties of a representative number of previously unknown 2-(alkylsulfanyl)quinolines, obtained from aryl isothiocyanates, allene or acetylene carbanions, and methyl iodide, upon electron ionization (70 eV) have been studied for the first time. All the studied compounds form a stable molecular ion, which is clearly detected in the mass spectra. All studied quinolines are characterized by common decay patterns, including the formation of [M – H]+, [M – Me]+, and [M – HS]+ ions. The main effect on fragmentation is exerted by the nature of substituents at positions 3 and 4 of the pyridine cycle of quinolines. The molecular ion of 4-methyl-2-(methylsulfanyl)-3-(1H-pyrrol-1-yl)quinolines electron ionization undergoes rearrangement, which occurs both with the participation of a sulfur atom and with the participation of a carbon atom of the methyl group in the 4 position of the heterocycle. Ways of fragmentation of the formed ions of the studied 2-(alkylsulfanyl)quinolines are proposed based on the analysis of the mass spectra of daughter ions.
Russian Journal of Organic Chemistry. 2025;61(6):687-700
687-700
Synthesis of Heterocycles Based on 4,5-Dichlorophthalonitrile
Resumo
The SNAr reaction of 4,5-dichlorophthalonitrile with various bifunctional nucleophiles was carried out in anhydrous DMF in the presence of K2CO3 as a deprotonating agent. It was shown that 4,5-dichlorophthalonitrile can be successfully employed in the synthesis of heterocyclic compounds; however, in some cases, these reactions may either give product mixtures or result in an unexpected rearrangement.
Russian Journal of Organic Chemistry. 2025;61(6):701-709
701-709
Catalytic Rearrangement of Four Substituted Tetrahydropyridine
Resumo
A new compound, 5-acetyl-2-amino-4-(2-chloro-5-nitrophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile, was synthesized by the reaction of 2-chloro-5-nitrobenzylidenemalononitrile with malononitrile and aniline. Subsequently, it was subjected to catalytic rearrangement in the presence of ethylenediamine and a second new compound, 4-(2-chloro-5-nitrophenyl)-6-oxo-2-(phenylamino)-1,4,5,6-tetrahydropyridine-3-carbonitrile, was obtained. The structure of the products was determined using NMR spectroscopy and X-ray diffraction analysis. A probable mechanism of the rearrangement reaction was proposed.
Russian Journal of Organic Chemistry. 2025;61(6):710-714
710-714
Dibenzoylmethane in the Synthesis of Selenium-Containing Di- and Tetrahydropyridine-3-carbonitriles
Resumo
Upon the interaction of cyanoselenoacetamide, 2-furan- or 2-thiophenocarbaldehydes and dibenzoylmethane in ethanol in the presence of an excess of piperidine or morpholine under argon, 6-hydroxy-3-cyano-1,4,5,6-tetrahydropyridine-2-ammonium selenolates were obtained, which were used in the synthesis of 2-alkylselenodi- and tetrahydropyridine-3- carbonitriles. The structure of the latter was studied using the method of X-ray diffraction analysis.
Russian Journal of Organic Chemistry. 2025;61(6):715-720
715-720
One-Pot Synthesis of 3,4-Dihydropyrimidino[2,1-a]isoindol-6(2H)-one
Resumo
One-pot synthesis of 3,4-dihydropyrimidino[2,1-a]isoindol-6(2H)-one, an analog of the promising anti-cancer drug batracilin, has been developed. Both acylation of 1,3-diaminopropane with phthalic anhydride and followed by cyclocondensation took place while heating in toluene or ortho-xylene. The highest yield 76% of the target isoindolone was obtained by adding 1,3-diaminopropane to phthalic anhydride in toluene, while reverse order of mixing the reagents, decreases the yield to 60%. The reaction proceeds stepwise, through the formation of 2-(3-aminopropyl)carbamoyl)benzoic acid, which is converted to isoindolone upon heating with 68% yield.
Russian Journal of Organic Chemistry. 2025;61(6):721-727
721-727
Synthesis Evaluation of Antibacterial Activity of New Derivatives of 1,3-Diaza-2-phenylamino-, 7-Amino-1,3,5-triaza-, 7-Carbamoylphenylamino-1,3,5-triazadamantanes
Resumo
A number of new derivatives of diaza- and triazadamantanes were synthesized and their antibacterial activity was studied by the interaction of 2-(4-aminophenyl)-5,7-disubstituted-1,3-diazadamantanes, 1,3,5-triazadamantan-7-amine and 1,3,5-triazadamantan-7-yl-(aminophenyl)methanones with anhydrides of substituted succinic and glutaric acids. Among the synthesized compounds, some possess moderate activity, suppressing the growth of gram-positive and gram-negative microorganisms in a zone with a diameter of d = 14–16 mm.
Russian Journal of Organic Chemistry. 2025;61(6):728-735
728-735
Reaction of Nitromethane with Phenylacetylene in Superbasic Media
Resumo
Nitromethane reacts with phenylacetylene in the KOH(t-BuOK)/DMSO superbase media to form E- and Z-isomers of 4-benzyl-3-styryl-4,5-dihydroisoxazole-2-oxide, 2-benzyl-3-hydroxypropanonitrile and 1-benzyl-2-nitrocyclopropane.
Russian Journal of Organic Chemistry. 2025;61(6):736-740
736-740
Enantioselective Aminomethylation of 1-(Benzyloxy)propan-2-one with 4-Methyl-2-[(prop-2-en-1-yl)oxy]aniline
Resumo
Enantioselective catalytic ternary aminomethylation of 1-(benzyloxy)propan-2-one with 4-methyl-2-[(prop-2-en-1-yl)oxy]aniline in the presence of a chiral catalyst pseudoephedrine in an aqueous medium leads to anti/syn products – optically pure aminoketoseters of the aromatic series with high yields. The structure of the obtained compounds was confirmed by 1H, 13C NMR spectroscopy and mass spectrometry data. Diasteromeric purity (de) was determined using chiral HPLC. This reaction can also be used to form a C-C bond. The ratio of diasteroeisomers was determined depending on the temperature and the solvent used.
Russian Journal of Organic Chemistry. 2025;61(6):741-745
741-745
Reaction of 1-antipyryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones with 1,3-Diphenylguanidine
Resumo
1-Antipyryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones react with 1,3-diphenylguanidine to form 6-antipyryl-9-aroyl-8-hydroxy-2-imino-1,3-diphenyl-1,3,6-triazaspiro[4.4]non-8-en-4,7-diones, the structure of which was confirmed by 'H NMR and IR spectroscopy.
Russian Journal of Organic Chemistry. 2025;61(6):746-749
746-749
Reaction of 1-Antipyryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones with Ethylenediamine
Resumo
Methyl 3-aroyl-2,4-dihydroxy-1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylates react with ethylenediamine to form methyl 5-aryl-8-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-6,7-dioxo-2,3,4,6,7,8-hexahydropyrrolo[2,3-e] [1,4]diazepine-8a(1H)-carboxylates, the structure of which was confirmed by NMR 1H and IR spectroscopy.
Russian Journal of Organic Chemistry. 2025;61(6):750-753
750-753
Synthesis and Antihypoxic Properties of New Derivatives 1,4-Benzodioxanil-1,3,4-oxadiazole
Resumo
Condensation of previously synthesized 1,4-benzodioxane-2-carboxylic acid hydrazide with chloranhydrides of various arylcycloalkane-, as well as aerylterrahydropyrancarboxylic acids substituted in the aromatic ring, gave N,N′-diacyl-substituted hydrazines, which are cyclized under the action of phosphorus oxychloride to the corresponding 1,3,4-oxadiazolebenzodioxanes. The antihypoxic properties of the synthesized compounds were studied.
Russian Journal of Organic Chemistry. 2025;61(6):754-760
754-760
Benzazoles. IV. Interaction of Benzimidazolin-2-ones with Chlorsulphonic Acid
Resumo
When benzimidazolin-2-ones interacted with chlorosulfonic acid in five different ratios (1 : 1–5) at 50–60°C, even when the reagents were used in equimolar amounts, 5-chlorosulfonylbenzimidazolin-2-ones were formed. In the case of 5-chlorobenzimidazoline-2-ones do not react with chlorosulfonic acid at 50–60°C and the corresponding 5-chlorosulfonyl-6-chlorobenzimidazoline-2-ones were synthesised at 110–120°C.
Russian Journal of Organic Chemistry. 2025;61(6):761-767
761-767
Iodination of Phenylacetylene and Some Transformations of the Resulting Iodine Derivatives
Resumo
An effective method for the iodination of phenylacetylene in the presence of cadmium (II) acetate at room temperature in DMSO is described, and the ratio of reagents is optimized. Mercuration-demercuration with iodine and oxidative homecoupling reactions of iodoethylhybenzene were carried out.
Russian Journal of Organic Chemistry. 2025;61(6):768-775
768-775
КРАТКОЕ СООБЩЕНИЕ
Recyclization of Pyrimidinium Salt – A Method for the Synthesis of Derivatives of Nitrogen-Containing Heterocycles
Resumo
By recyclization of 1,4,6-trimethyl-2-ethoxycarbonylmethylpyrimidinium iodide under the action of ethylhydrazine and 4,6-dimethylpyrimidinyl-2-acetic acid hydrazide, 1-ethyl-3-ethoxycarbonylmethyl-5-methyl-1,2,4-triazole and 5,7-dimethyl-3-ethoxycarbonyl-2-(4',6'-dimethyl-yrimidinyl-2')methylpyrazolol[1,5]-alpyrimidine were synthesized, respectively. Alkylation of 1-ethyl-3-ethoxycarbonylmethyl-5-methyl-1,2,4-triazole with various alkyl iodides yielded the corresponding N-alkyltriazolium salts, and reactions of triazolylacetic acid esters yielded their hydrazides. Based on the nuclear Overhauser effect (NOE), it was clearly demonstrated that alkylation occurs at the N-4 nitrogen atom of the triazole ring.
Russian Journal of Organic Chemistry. 2025;61(6):776-782
776-782