Russian Journal of Organic Chemistry最新文献

The KHMDS-promoted reaction of (3R)-3-(1-ethoxyethoxy)-4,4-dimethyltetrahydrofuran-2-ol with 5-(methylsulfonyl)-1-phenyl-1H-tetrazole forms 5-{[(2S,3R)-3-(1-ethoxyethoxy)-4,4-dimethyltetrahydrofuran-2-yl]oxy}-1-phenyl-1H-tetrazole, an anomalous heteroaryl pantolactone acetal.

A series of new thiazole derivatives containing quinoline moieties were synthesized in two step reactions as the study of potential antimicrobial and antioxidant activities. All synthesized compounds were characterized by IR, ¹H, ¹³C NMR, HMBC, and HSQC spectral techniques and elemental analysis. In antimicrobial and antioxidant studies, compound 2b displayed remarkable activity with highest inhibition value 28 ± 0.5 mm against S. typhimurium and showed significant antioxidant activity with IC₅₀ value 28.49 ± 1.3 µg/mL as compared to the standard Ascorbic acid (IC₅₀ 49.67 ± 3.38 µg/mL). Molecular docking studies also agreed with significant basis for antimicrobial and antioxidant activities.

β-Iodovinyl sulfones were synthesized in high yields (89–99%) via a regioselective radical double functionalization of terminal arylalkynes with tosyl iodide, using equivalent reagent amounts. This efficient reaction was performed under irradiation with red light of 625 nm from an economical LED light source.

N,N'-(Hexane-1,6-diyl)bis(1-R-3,3-dimethyl-3,4-dihydroisoquinoline-2(1H)-carboxamides) have been synthesized by reacting 1-R-3,3-dimethyl-1,2,3,4-tetrahydroisoquinolines (R = H, Me) with hexamethylene diisocyanate (HDI). The reaction of HDI with 1,3,3-trimethyl-3,4-dihydroisoquinoline gave (2Z, 2Z')-N,N'-(hexane-1,6-diyl)bis[2-(3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene)acetamide], and a similar product was obtained from the corresponding benzo[f]isoquinoline. Both bisamides have been previously prepared by an independent synthesis via the Ritter cyclization. The reaction of HDI with enamine amides of the 6,7-diethoxy-1-methylidene-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline series involved carbamoylation at the β-carbon atom of the enamine fragment, leading to bis(malonamide) derivatives.

Over the past decade, green synthesis principles have driven the research and development of recyclable catalysts and renewable resources in organic chemistry. Among these, nanoparticles have emerged as particularly effective and environmentally friendly catalysts. This review presents the first comprehensive report on the use of such nanoparticles in the synthesis of carbazoles and their derivatives—a class of privileged scaffolds in drug discovery. We summarized recent advances in nanoparticle-catalyzed synthesis of these pharmacologically important molecular frameworks.

Cycloaddition of (R)-(–)-carvone and nitrile imine generated in situ from N-phenylbenzenecarbo­hydrazonoyl chloride in the presence of triethylamine afforded (3aS,5R,7aS)-7a-methyl-1,3-diphenyl-5-(prop-1-en-2-yl)-1,3a,4,5,6,7a-hexahydro-7H-indazol-7-one as the major product. Its structure was determined by spectral methods.

Cyanoselenoacetamide reacted with 1-aryl-2-bromoethanones in ethanol or DMF to give 4,6-di­amino-2-[(2-aryl-2-oxoethyl)selanyl]pyridine-3-carbonitriles in 68–93% yields.

Nucleophilic addition of urea and thiourea to 1-antipyryl-1H-pyrrole-2,3-diones afforded 1-anti­pyryl-4-aroyl-3-hydroxy-5-methoxycarbonyl-5-ureido-1H-pyrrol-2-ones and 1-antipyryl-4-aroyl-3-hydroxy-5-methoxycarbonyl-5-thioureido-1H-pyrrol-2-ones. 1-Antipyryl-4-aroyl-3-hydroxy-5-methoxycarbonyl-5-ureido-1H-pyrrol-2-ones underwent intramolecular spiro heterocyclization by the action of sodium methoxide.

N-[4-(4-Azidobenzyl)phenyl]acetamide and 4-(4-azidobenzyl)phenol have been synthesized in 57 and 55% yields, respectively, by the diazotization of N-[4-(4-aminobenzyl)phenyl]acetamide and 4-(4-amino­ben­zyl)­phenol with sodium nitrite in excess hydrochloric acid, followed by treatment of the resulting diazonium salts with sodium azide at 0 to –5°C.

New quinoline–benzimidazole hybrids 3a–3d have been synthesized from 1-(quinolin-5-yl)­ethanone and benzene-1,2-diamine and converted to the corresponding N-tosyl (4a–4d) and N-methyl derivatives (5a–5d). The synthesized compounds were characterized by IR, NMR, and mass spectra. Compounds 4a and 4c demonstrated exceptional anticancer efficacy against HeLa cell line. Compounds 4a and 4d, however, were more active against HT-29 cell line.