Russian Journal of Organic Chemistry最新文献

The review systematizes the literature on the methods for preparing nitroquinoline derivatives over the past 10–15 years. The synthetic methods are categorized based on key chemical reaction.

A previously unknown family of 9-selenabicyclo[4.2.1]nonane derivatives was obtained in up to 98% yields by the transannular addition reaction of selenium dihalides with 1,3-cyclooctadiene. Conditions for selective anti,anti and syn,anti (endo–exo diastereomer) additions to obtain the endo–endo or endo–exo diastereomers, respectively, were found. An approach to selectively introducing two target substituents into selenabicyclo[4.2.1]nonane, including isomerization of the endo–exo diastereomer into the endo–endo derivative, was developed.

Eugenol, a natural product with diverse biological activities, exhibits significant potential as a lead compound for clinical drug development. In this study, we designed and successfully synthesized six novel 1,3,4-thiadiazole eugenol derivatives and evaluated their antibacterial activity. Two of the synthesized compounds exhibited moderate antibacterial activity against Staphylococcus aureus, displaying minimum inhibitory concentrations (MICs) that were equal to or lower than the MIC of gentamicin (16 and 32 µg/mL vs. 32 µg/mL, respectively). These findings suggest that further structural optimization and mechanistic studies are warranted to enhance the antibacterial potency of the synthesized eugenol derivatives.

A convenient and an accessible method for the synthesis of novel heterocyclic hybrid systems—3-[2-(1H-benzo[d]imidazol-2-yl)ethyl)-4-methylquinolin-2(1H)-ones, 3-(2-(benzo[d]oxazol-2-yl)ethyl)-4-methylquinolin-2(1H)-ones, and 3-(2-(benzo[d]thiazol-2-yl)ethyl)-4-methylquinolin-2(1H)-ones—was developed. The synthesis was carried out by reacting ethyl 3-(4-methyl-2-oxo-1,2-dihydroquinolin-3-yl)propanoates, substituted in the benzene ring, with o-phenylenediamine, o-aminophenol, and o-aminobenzenethiol.

A series of symmetrical bis-benzimidazole, bis-benzoxazole, and bis-benzothiazole derivatives were synthesized through a double Phillips-type cyclocondensation between ethylenediaminetetraacetic acid (EDTA) and a set of ortho-substituted aniline precursors. EDTA serves as a polycarboxylic substrate enabling the simultaneous formation of two heterocyclic rings in a single step under strong acidic conditions. Structural elucidation of the ten obtained compounds was confirmed by ¹H and ¹³C NMR spectroscopy, HRMS, and comparison with reported data. The observed molecular masses and NMR profiles unambiguously support the formation of bis-heterocyclic structures. Yields ranged from 49% to 73% depending on the nature of the heteroatom (O, S, or N), reflecting the higher nucleophilicity of sulfur leading to improved cyclization efficiency. Corrected synthetic schemes and a mechanistic rationale are presented.

Amberlyst A21, a solid ion-exchange resin, is known as a practical and recyclable catalyst for the synthesis of Hantzsch polyhydroquinolines providing an environmentally friendly option to produce pharmaceutically significant polyhydroquinoline derivatives. The present research illustrates the effective utilization of Amberlyst A21 for a one-pot, multicomponent reaction that includes aldehyde, ethyl acetoacetate, dimedone and ammonium acetate under ultrasonic irradiation at room temperature. The method significantly enhances the reaction rate and product yield, providing high yields without hazardous solvents or chromatographic purification. The catalyst’s recyclability and environmental compatibility make it an attractive choice for sustainable organic synthesis. The synthesis process is optimized by evaluating various solvents and catalyst loadings, demonstrating its potential for industrial-scale applications. Overall, this work contributes to the ongoing development of green chemistry in pharmaceutical research by providing an economical, efficient, and environmentally friendly method for synthesizing polyhydroquinoline derivatives.

A new strategy for one-pot synthesis of quaternary phosphonium salts with an ester group was developed and applied to obtain previously unknown a series phosphonium salts by reacting triphenylphosphine with halocarboxylic acids in an alcoholic medium. The alkylation of carboxylate phosphabetaines with alcohols in an acidic medium was studied. The structures and compositions of all synthesized compounds were confirmed by IR and ³¹P and ¹³C NMR spectroscopy and elemental analysis. The structure of the phosphonium salts was verified using single-crystal X-ray diffraction analysis. In vitro antimicrobial screening showed that the synthesized phosphonium salts exhibited notable inhibition zones against Gram-positive strains.

Functionally substituted 1-benzofurans were synthesized via a three-component condensation of diatomic phenols, phenylglyoxal hydrate, and active methylene compounds. In the reaction employing pyrocatechol, the initially formed adduct does not undergo further cyclization.

A synthetic approach was developed for novel bifunctional organochalcogen compounds based on the reactions of tellurium, selenium, and sulfur halides with allylacetic acid, affording products in 86–99% yields. Reactions with sulfur and selenium dihalides yielded chalcogenides containing two methylbutyrolactone moieties in 97–99% yields. Reactions with tellurium tetrachloride and tetrabromide produced trihalotellanes containing a methylbutyrolactone group. The reaction of TeBr₄ with allylacetic acid in methanol involved methoxytelluration accompanied by transesterification, forming a tribromotellane with methoxy and methoxycarbonyl functionalities. The resulting trihalotellanes were reduced to the corresponding functional ditellurides in high yields.

Twenty four new diazaadamantane derivatives have been synthesized by reacting 5.7-dialkyl-6-oxo-1,3-diazaadamantanes with aromatic aldehydes and dialdehydes. Some of the products were tested for antioxidant activity.