Russian Journal of Organic Chemistry最新文献

Effects of different conditions on the reaction of alkenes with phenyl[(trifluoromethanesulfonyl)­imino]-λ³-iodane (PhI=NTf, 1) have been studied. The reaction of PhI=NTf with styrenes in the presence of copper(I) chloride led to the formation of substituted aziridine and bis-trifluorometanesulfonamido derivatives at different ratios. When silver nitrate was used as additive in the same reaction, 1-phenyl-2-(trifluoro­methanesulfonamido)ethyl nitrate was formed. Isomeric amidines were obtained from camphene as substrate in the presence of different activating additives and an oxidant. Potential biological activity of the synthesized compounds was predicted using PASS Online software.

1,2-Addition of lithiated 4-hydroxy-4,5-dimethylhept-1-yne to the keto group of ethyl 7-(5-oxocyclopent-1-en-1-yl)heptanoate, followed by in situ oxidative isomerization of the adduct afforded 11-deoxy-13,14-didehydro-17-methyl-20-norprostaglandin B₁ (PGB₁) ethyl ester.

1,3-Dihydro-2H-benzimidazol-2-ones reacted with chlorosulfonic acid at 50–60°C to give 5-chloro­sulfonyl-1,3-dihydro-2H-benzimidazol-2-ones regardless of the reactant ratio (1:1 to 1:5). 5-Chloro-1,3-dihy­dro-2H-benzimidazol-2-ones failed to react with chlorosulfonic acid at 50–60°C, and the corresponding 5-chloro-6-chlorosulfonyl derivatives were obtained at 110–120°C.

In order to obtain amide compounds with enhanced antifungal activity, twelve 2-aminothiazole derivatives were synthesized using combinatorial chemistry techniques. The newly synthesized compounds were characterized by using various techniques such as ¹H NMR, ¹³C NMR, ESI-MS, and elemental analysis. Notably, compound 11b not only exhibited a high inhibitory rate against Sclerotinia sclerotiorum but also possessed certain anticancer effects. Molecular docking analysis provided a scientific basis for how this compound achieves its antifungal effects.

Pyrazolyl-substituted chromene analogues have been synthesized in one pot from 1H-pyrazole-5-carbaldehydes, malononitrile, and cyclohexane-1,3-dione or dimedone in the presence of L-proline as catalyst using ethanol as solvent under reflux conditions for 2–3 h. This approach offers notable advantages such as high yields, environmental friendliness, easy experimental procedure, short reaction time, and mild reaction conditions.

N-Methylmorpholinium 4-aryl-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates reacted with hydrogen sulfide and formaldehyde in ethanol to give 5-aryl-4-sulfanylidene-2,3,4,5,6,8-hexahydro-7H-pyrido[3,2-e][1,3]thiazin-7-ones. The molecular and crystal structures of N-methylmorpholinium 5-cyano-2-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydropyridine-6-thiolate were determined by X-ray analysis.

Methyl 3-aroyl-1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2,4-dihydroxy-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylates reacted with ethylenediamine to give 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 product structure was confirmed by ¹H NMR and IR spectra.

A series of adamantyl-containing alkenes were synthesized by the alkenylation of adamantan-1-ol with secondary alcohols in the presence of sulfuric acid. The scope of application of this reaction was explored to show that the alkenylation reaction with symmetrical dialkylcarbinols occurs in a selective fashion. The alkenylation of adamantan-1-ol with sec-pentanol and its higher homologs gives a mixture of isomeric alkenes. The reactions of substituted adamantanols with isopropanol, butan-2-ol, and cyclohexanol in the presence of sulfuric acid were studied, and a series of new unsaturated derivatives of the adamantane series were obtained.

Novel Schiff base derivatives were synthesized, starting from 1-[2-methyl-4-sulfanylquinolin-3-yl]propan-2-ones and 1-[2-methyl-4-(methylsulfanyl)quinoline, substituted in the benzene ring. To obtain the Schiff base derivatives containing the 4-(methylsulfanyl) group, the corresponding 4-sulfanylquinoline-propan-2-ones and 3-(2-chloroallyl)-4-sulfanylquinolines were methylated, and then the chloroallyl group in the resulting 3-(2-chloroallyl)-4-(methylsulfanyl)quinolines was subjected to acid hydrolysis.

An overview of the main scientific achievements of Russian universities in the field of organic chemistry over the period 2018–2023 is presented.