Anvar Abdushukurov

In this study, an efficient and regioselective synthetic method was developed for the preparation of 3-hydroxy-3-((2-(naphthalen-2-yloxy)-2-oxoethoxy)carbonyl)pentanedioic acid, a multifunctional ether–ester compound of potential interest for pharmaceutical and material science applications. The target compound was synthesized via the nucleophilic substitution (SN2) and esterification reactions of 2-naphthyl chloroacetate with the monosodium salt of citric acid. Optimization of the reaction conditions was carried out by varying the molar ratio of the reagents, reaction temperature, and duration. The highest yield of 83% was achieved under the conditions of a 2:1 molar ratio of chloroacetate to citrate, a temperature of 70–80 °C, and a reaction time of 6 h. The enhanced product yield observed under these conditions is attributed to the dual reactivity of the citric acid monosodium salt, which contains a free hydroxyl group capable of undergoing SN2 etherification, and free carboxylic acid groups that participate in esterification with the electrophilic 2-naphthyl chloroacetate. The stoichiometric 2:1 ratio ensures that both reactive centers on the citrate anion are fully utilized, leading to efficient and selective transformation into the desired product. Mechanistically, the ether bond formation proceeds through the classical Williamson ether synthesis pathway, where the alkoxide formed from the hydroxyl group attacks the electrophilic carbon of the chloroacetate, displacing the chloride ion. Concurrently, esterification enhances molecular complexity and stability. The results underline the synthetic utility of citric acid derivatives in forming complex organic architectures via environmentally benign routes. This study not only contributes a practical approach to multifunctional molecule synthesis but also reinforces the applicability of green chemistry principles in ester–ether coupling strategies.

The synthesis, crystal structure, and Hirshfeld surface analysis of N-(4-methoxyphenyl)picolinamide (MPPA), C₁₃H₁₂N₂O₂, are presented. MPPA crystallizes in the monoclinic space group P2₁/n, with a single molecule in the asymmetric unit. Structural analysis reveals that all non-hydrogen atoms are nearly coplanar, and the molecule exhibits two intramolecular hydrogen bonds that stabilize its conformation. Supramolecular features include significant intermolecular interactions, primarily C—H...π and various hydrogen bonds, contributing to the overall crystal cohesion, as confirmed by energy framework calculations yielding a total interaction energy of −138.3 kJ mol⁻¹. Hirshfeld surface analysis indicates that H...H interactions dominate, followed by C...H and O...H interactions, highlighting the role of van der Waals forces and hydrogen bonding in crystal packing.

The aim of the study is to develop a convenient method for the synthesis of O-chloroacetylthymol and to propose the mechanism of the O-chloroacetylation reaction. Thin-layer chromatography of chloroacetylation and nucleophilic substitution reaction products was studied and their composition was confirmed by reference substances. Nucleophilic exchange reactions of O-chloroacetylthymol with sodium oxalate, sodium tartrate, potassium rhodanides were studied. Favorable conditions for carrying out the nucleophilic exchange reaction were searched and 3 new substances unknown in the literature were synthesized. The structure of the synthesized substances was proved by IR and NMR spectra.

The purpose of the research is study of the reaction between natrium salt of oxalic acid and O-chloracetyl tymole in presence of dimethylformamide. High yields have been achieved by the reaction of di(2-isopropyl-5-methylphenylcarboxymethylene)oxalates in the presence of dimethylformamide as a solvent. The structure of the prepared compounds are installed by means of IR and NMR spectroscopy.

The chemical reaction of O-chloroacetylthymol with the sodium salt of tartaric acid in the presence of dimethylformamide and hexamethylphosphoramide (HMPA) as solvents is described in this article, along with the findings of physico-chemical analysis to confirm the structure of the resulting chemical compounds. Hexamethylphosphoramide was found to be present in the chemical reactions which were proven to have the greatest yields (HMPA).