Russian Journal of Organic Chemistry最新文献

1,2,3-Triazole moieties with various substituent groups were introduced into the structure of dolutegravir, yielding numerous novel derivatives. These compounds exhibited excellent inhibitory activity against a range of tumor cells, including KYSE30, KYSE140, NE3, AGS, MiaPaCa2, and SKOV3 cells. Most of the compounds exhibited potent effects on MiaPaCa2 cells. Specifically, compounds 4b, 4e, 4f, and 4h demonstrated promising inhibitory activities against MiaPaCa2 cells, with IC₅₀ values of 0.86±0.35, 1.01±0.27, 1.69±0.53, and 1.17±0.37 μM, respectively. Additionally, compounds 4b, 4e, 4f, and 4h induced apoptosis in MiaPaCa2 cells, and compounds 4e, 4f, and 4h induced cell cycle arrest in the G2/M phase. These findings suggest that dolutegravir derivatives are promising candidates for treating MiaPaCa2 tumors.

A series of novel heterocyclic hydroxamic acid derivatives have been synthesized and characterized by ¹H and ¹³C NMR and high-resolution mass spectra and elemental analyses. The synthesized derivatives are of interest as potential chelating agents and multifunctional agents in various scientific and technological domains.

Two alternative synthetic routes to 7,7-dimethyl-3-azabicyclo[4.1.0]heptan-4-one have been developed via intramolecular cyclization of acyclic blocks obtained from (+)-3-carene.

1,3-Dipolar addition of dimethyl (1-diazo-2-oxopropyl)phosphonate (Ohira–Bestmann reagent) to arylmethylideneimidazolones afforded substituted pyrazolylphosphonates.

The past two decades have witnessed remarkable advancements in organocatalysis, with small organic molecules like L-proline emerging as key players in green and sustainable synthesis. Awarded the 2021 Nobel Prize in Chemistry for its role in asymmetric organocatalysis, this field offers eco-friendly alternatives to conventional catalytic methods. L-Proline, a naturally occurring amino acid, has gained prominence due to its ability to efficiently catalyze a diverse array of organic reactions, often with high enantioselectivity and yield. Acting via iminium or enamine intermediates, L-proline facilitates reactions such as aldol, Knoevenagel, Mannich, Biginelli, Michael, and other reactions. It also demonstrates utility in heterocyclic chemistry, enabling one-pot multi-component syntheses under mild water-tolerant conditions. Recent innovations include the development of L-proline derivatives for advanced asymmetric syntheses, such as the (S)-Wieland–Miescher ketone and carbohydrate-conjugated pyranoquinolones, expanding the scope of this organocatalyst. Additionally, applications in chemosensors, anticancer agents, and biaryl glycosides underscore its versatility. This review highlights L-prolineʼs mechanistic pathways, including iminium and enamine catalysis, comparative advantages over traditional methods, and its pivotal role in promoting green chemistry. As research continues to refine its derivatives, L-proline remains an indispensable tool for sustainable and efficient organic synthesis.

The addition of benzoic and phenylacetic acids to 8-acetoxy- and 8-(acetoxymethyl)tetra­cyclo­[4.4.1^2,5.1^7,10.0^1,6]dodec-3-ene in the presence of boron trifluoride–diethyl ether complex as catalyst afforded mixed benzoic/acetic and phenylacetic/acetic bis-esters with tetracyclo[4.4.1^2,5.1^7,10.0^1,6]dodecanediol and 2-hydroxytetracyclo[4.4.1^2,5.1^7,10.0^1,6]dodec-8-ylmethanol in 73–80% yields. The product structure was confirmed by their IR and ¹H and ¹³C NMR spectra.

5-Substituted-1H-tetrazoles can be synthesized from the corresponding nitriles by reaction with NaN₃ using the efficient and green onion extract catalyst under microwave irradiation and solvent- free conditions in good to excellent yields (up to 95%) and very short reaction times. This method is applicable to a wide range of aryl and alkyl nitriles with sodium azide in solvent-free media, and affords the various tetrazole derivatives in an eco-friendly solvent-less procedure under microwave irradiation at reaction temperature 120°C. The use of onion extract makes the process environmentally benign.

The alkylation of dimethyl acetonedicarboxylate with halogen derivatives in the presence of potassium carbonate in dimethyl sulfoxide at 60–70°C led to the formation of C- and O-alkylation products. The O-alkyl derivatives rearranged to the corresponding C-alkyl isomer on heating above 180°C. The reactions of the title compound with ethyl 2-bromopropanoate and 1,3-dichloroacetone under similar conditions involved both methylene groups of the substrate. The product of O-alkylation of dimethyl acetonedicarboxylate with bromoacetaldehyde diethyl acetal is stable up to 200°C; however, hydrolysis of the acetal moiety gave the corresponding aldehyde which isomerized to C-(2-oxoethyl) derivative, followed by intramolecular cyclization to substituted furan. The reaction of dimethyl acetonedicarboxylate with chloroacetonitrile produced C-(cyano­methyl) derivative which cyclized to α-aminofuran in acidic medium.

Previously unknown 1,5-diaryl-2-(2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene)malononitriles have been synthesized by the reaction of enamines with oxalyl chloride, followed by the condensation of intermediate pyrrole-2,3-diones with malononitrile.

The molecular (bond lengths and bond and nonbonded angles) and electronic parameters (ground state spin multiplicity and charge distribution over particular atoms) of (6666)macrotetracyclic 3d-metal chelates (M = Ti, V, Cr, Mn, Fe, Co, Ni, Cu) with phthalocyanine as an NNNN-donor ligand and two axial fluoro ligands have been calculated at the DFT B3PW91/TZVP level of theory. All these chelate complexes have pseudooctahedral or close to it structure, where the metal ion is located in the plane formed by the four donor nitrogen atoms. The M–N bond lengths, as well as M–F bond lengths, in most of these metal complexes are equal to each other. All 5- and 6-membered rings in each complex are identical to each other both in the sum of the bond angles and in their set. Standard thermodynamic characteristics (enthalpies, entropies, and Gibbs energies) of the formation of these metal chelates have also been determined.