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Vol 61, No 2 (2025)

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Articles

SYNTHESIS OF 1,2-DISUBSTITUTED-3-THIOINDOLES BY THE MADELUNG REACTION

Sterligov G.K., Rasskazova M.A., Topchiy M.A., Asachenko A.F.

Abstract

The synthesis of 1,2-disubstituted-3-thioindoles was performed by the Madelung reaction from available starting compounds – benzylsulfides. Under the found conditions [0.2 M benzylsulfide solution in THF, 2 eq LDA], 1,2-disubstituted-3-thioindoles with electron-donor and electron-acceptor substituents at the 5 and 6 positions, as well as with aromatic and aliphatic substituents at the sulfur were obtained. The products were obtained in high yields (from 62 to 93%).
Žurnal organičeskoj himii. 2025;61(2):125-132
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Synthesis and chemical properties of derivatives of E-3-[3-(2,5-dihydro-2,5-dioxo-1h-pyrrole-1-yl)phenyl]propenoic acid

Kolyamshin O.A., Mitrasov Y.N., Danilov V.A., Avruyskaya A.A., Pylchikova Y.Y.

Abstract

By the reaction of m-aminocoric acid with maleic anhydride in an acetone medium, Z-4-{3-(E-2-carboxyethenyl)phenylamino}-4-oxo-2-butenic acid was synthesized, intramolecular cyclization of which in the presence of p-toluene sulfonic acid E-3-[3-(2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl)phenyl]propenic acid. It has been shown that the interaction of the potassium salt of m-aminocortic acid with 2-bromomethyl-1,1-dichlorocyclopropane proceeds chemoselectively while maintaining a three-membered cycle and leads to the formation of E-2,2-dichlorocyclopropylmethyl-3-(3-aminophenyl)propenoate, on the basis of which, under the sequential action of maleic and acetic anhydrides in the presence of sodium acetate, E-2,2-dichlorocyclopropylmethyl-3-[3-(2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl)phenyl]propenoate was obtained. It was found that under the action of secondary amines, it reacts with aza-Michael to form 2,2-dichlorocyclopropylmethyl-3-[3-(3-R2N-2,5-dioxo-2,3,4,5-tetrahydro-1H-pyrrol-1-yl)phenyl]propenoates.

Žurnal organičeskoj himii. 2025;61(2):133-140
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SYNTHESIS OF A NEW 2,4,6(1Н,3Н,5Н)PYRIMIDINETRIONE DERIVATIVES

Velikorodov A.V., Kutlalieva E.N., Kotova V.Y., Shustova E.A.

Abstract

Condensation of 5-acetyl-2,4,6(1H,3H,5H)-pyrimidinetrione with 3-fluoro-, 4-fluoro-, 2-methoxy-3,5-dichlorobenzaldehydes and methyl (4-formyl-2-oxo-2H-chromen-7-yl)carbamate in 1-BuOH in the presence of piperidine and acetic acid by boiling for 4 hours gave the corresponding 5-[(E)-3-aryl-2-propenoyl]-2,4,6(1H,3H,5H)-pyrimidinetriones) and methyl N-2-oxo-4-[(E)-3-oxo-3-(2,4,6-trioxohexahydro-5-pyrimidinyl)-1-propenyl]-2H-chromen-7-ylcarbamate. Reaction of 3-methoxy-4-hydroxy-, 3,5-dimethoxy-4-hydroxy-benzaldehydes with 5-acetyl-2,4,6(1H,3H,5H)-pyrimidinetrione in dioxane in the presence of boron trifluorideetherate at room temperature completes after 48 hours with the formation of the corresponding chalcones. The corresponding imines and 5-arylidene derivatives were obtained by condensation of barbituric acid with alkyl C-nitroso phenylcarbamates in methanol and hydroxy-substituted benzaldehydes in water. The condensation of 5-[(4-hydroxy-3,5-dimethoxyphenyl)methylene]-2,4,6(1H,3H,5H)-pyrimidinetrione with aminoguanidine bicarbonate results in the formation of 7-hydrazinyl-5-(4-hydroxy-3,5-dimethoxyphenyl)pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione. Cyclocondensation of 2,4,6(1H,3H,5H)pyrimidinetrione with methyl N-{3-[(E)-3-(4-methoxyphenyl)-2-propenoyl]phenyl}carbamate in acetic acid in the presence of P2O5 yielded methyl { 3-[5-(4-methoxyphenyl)-2,4-dioxo-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]pyrimidin-7-yl]phenyl}carbamate.

Žurnal organičeskoj himii. 2025;61(2):141-150
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Synthesis of macrocyclic dithiadiperoxyspiroalkanes with the participation of lanthanide catalysts

Makhmudiyarova N.N., Ishmukhametova I.R., Dzhemilev U.M.

Abstract

An effective method has been developed for the synthesis of macrocyclic dithiadiperoxyspiroalkanes by cyclocondensation of alkane-α,ω-dithiols (butane-1,4-, pentane-1,5-, hexane-1,6-dithiols) with 1,1-dihydro-peroxycycloalkanes and formaldehyde with lanthanide catalysts.
Žurnal organičeskoj himii. 2025;61(2):151-158
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Synthesis and antiproliferative activity of 2-aryl-aminopyrimidine amides of benzimidazole-substituted phenylcarboxylic acid – new potential protein kinase inhibitors

Koroleva E.V., Ermolinskaya A.L., Ignatovich Z.V., Panibrat O.V., Hoang T.K., Huynh T.K., Nguyen T.C.

Abstract

The results of a study on the synthesis and antiproliferative activity of new phenylcarboxylic acid amides, the structure of which contains pharmacophoric fragments of nitrogen-containing heterocycles – 2-aminopyrimidine, benzimidazole, pyridine, are presented. The synthesis was carried out by acylation of substituted 2-arylaminopyrimidine phenylenediamines with p-benzimidazole-phenylcarboxylic acid chloride or by aminolysis of p-benzimidazolephenylcarboxylic acid with 2-arylaminopyrimidinephenylenediamines. The potential inhibitory activity of the synthesized amides was assessed by in vitro screening of the compounds for antiproliferative activity in models of stable human tumor cell lines K562, HL-60, RPMI 1788, HeLa.
Žurnal organičeskoj himii. 2025;61(2):159-166
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Synthesis of (3aS,4S,6aR)-2-oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-4-yl acetate, as a key synthon in approaches to (–)-galiellalactone

Gimazetdinov A.M., Zagitov V.V., Makaev Z.R., Miftakhov M.S.

Abstract

The synthesis of bicyclic allyl acetate 2, a promising precursor of (-)-galileolactone 1, is described. The approach is based on the separation of diastereomeric carboxamides obtained by amidation of racemic gem-dichloro-substituted Grieco lactone with (+)-α-methylbenzylamine. Subsequent steps of transformation of an individual diastereomer include reactions of complete reductive dechlorination, construction of an allyl alcohol fragment in the ring part by stereo- and regiospecific bromohydroxylylation with NBS in aqueous THF, and dehydrobromination.
Žurnal organičeskoj himii. 2025;61(2):167-171
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Reaction of 1-antipyryl-4-aroyl-5-methoxyra bonyl-1H-pyrrol-2,3-diones with N-substituted- and N-unsubstituted 3-amino-5,5-dimethylcyclohexen-2-ones

Lyadov V.A., Denislamova E.S., Maslivets A.N.

Abstract

The article considers nucleophilic transformations of N-antipyryl-substituted-1H-pyrrole-2,3-diones under the action of dimedone imine and N-substituted dimedone imines, acting as 1,3-CH,NH-binucleophilic reagents, with the formation of 1'-antipyryl-3'-aroyl-4'-hydroxy-6,6-dimethyl-6,7-dihydrospiro[indole-3,2'-pyrrole]-2,4,5'(1H,1'H,5H)-triones and 1'-antipyryl-1-aryl-3'-aroyl-4'-hydroxy-6,6-dimethyl-6,7-dihydrospiro[indole-3,2'-pyrrole]-2,4,5'(1H,1'H,5H)-triones.
Žurnal organičeskoj himii. 2025;61(2):172-177
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Interaction of maleimides and itaconimides with carboxymethyleneazine binucleophiles

Kulichikhina Y.Y., Medvedeva S.M., Nechaev I.V., Kovygin Y.A., Present M.A., Nikitenko D.V., Shikhaliev K.S.

Abstract

The nature of the interaction of N-arylmaleimides and N-arylitaconimides with some carboxymethyleneazines has been studied. The reaction of itaconic acid imides with oxopiperazinylidene acetates and oxomorpholinylidene acetate leads to imide recyclization and the formation of pyridine-containing heterosystems. The interaction of N-arylitaconimides and N-arylmaleimides with oxoquinoxalinylidene acetate involves Michael addition with the formation of linear adducts. The features of this process have been substantiated using quantum-chemical calculations.
Žurnal organičeskoj himii. 2025;61(2):178-191
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REDUCTION OF PEROXIDE PRODUCTS OF OZONOLYSIS OF CYCLOOCTENE BY SEBACIC ACID DIHYDRAZIDE

Yakovleva M.P., Kravchenko A.A., Saitov K.M., Nazarov I.S., Ishmuratova N.M., Ishmuratov G.Y.

Abstract

It was found that the reduction of ozonolysis peroxide of cyclooctene products by sebacic acid dihydrazide in solvents of various natures leads to the formation of three acyclic differently functionalized cyclooctene derivatives: in methanol – dimethyl 11,20-dioxo-9,10,21,22-tetraazatriacont-8E,22E-dienoic acid, in methylene chloride – 11,20-dioxo-9,10,21,22-tetraazatriacta-8E,22E-diene acid, in THF – natural cortic acid.
Žurnal organičeskoj himii. 2025;61(2):192-196
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Study of Reaction of (E)-(3-Aryl-3-oxoprop-1-en-1-yl) triphenylphosphonium Bromides with 2-Aminopyridine

Khachikyan R.D., Harutyunyan K.K., Ayvazyan A.G., Hovakimyan Z.G.

Abstract

(E)-(3-Aryl-3-oxoprop-1-en-1-yl)triphenylphosphoniumbromides react with 2-aminopyridine to form [(2-aryl-3-imidazo-[1,2-α-]pyridin-3-yl)methyl]triphenylphosphoniumbromides. An alternative scheme of the reactions is proposed, including an initial attack of the nucleophile on the carbonyl group.
Žurnal organičeskoj himii. 2025;61(2):197-202
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New chemical transformation of substituted dinitroacetonitrilе in the reaction with isoquinoline in presence of dimethylbut-2-indioate

Tyrkov A.G., Yurtaeva E.A.

Abstract

The reaction of substituted dinitroacetonitrile with isoquinoline in the presence of dimethylbut-2-indioate results in the formation of 1,3-dipolar cycloaddition products – a mixture of diastereomeric dimethyl-2-dinitromethyl-1,1bH-pyrimido[2,1-a]isoquinoline-3,4-dicarboxylates. The obtained compounds can be considered as promising synthons with potential antituberculosis and fungicidal activity.
Žurnal organičeskoj himii. 2025;61(2):203-207
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Ammonium salts as convenient ammonia surrogates in the Willgerodt reaction

Kvetkin E.A., Sokolov A.V.

Abstract

A novel solventless modification of the Willgerodt reaction is proposed. It employs elemental sulfur and ammonium salts as safe and convenient surrogates of ammonia on a solid carrier. The reaction involving combination of ammonium carbonate and aluminum oxide results in the amides of aryl acetic acids with yields from 48 to 85%.
Žurnal organičeskoj himii. 2025;61(2):208-214
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