Žurnal organičeskoj himii

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%).

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.

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.

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.

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.

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.

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%.