SYNTHESIS OF ACETYLENIC ALCOHOLS BASED ON CYCLOPROPYLACETYLENE AND AROMATIC ALDEHYDES AND THEIR MOLECULAR DOCKING ANALYSIS AGAINST THE NOX2 RECEPTOR

In this research work, the nucleophilic addition reaction of cyclopropylacetylene with aromatic aldehydes was investigated in the presence of a catalytic system consisting of EtMgCl/C17H29NO/TFE. Within the scope of the study, the reactivity of benzaldehyde derivatives containing various functional groups (fluoro, chloro, bromo, alkyl, alkoxy, and hydroxyl) as well as structurally complex anthracene-9-carbaldehyde substrates was analyzed.The proposed synthetic method does not require expensive metals as catalysts or ultra-low temperatures.This methodology is considered cost-effective and convenient, enabling the preparation of structurally diverse acetylenic alcohols with high chemical yields (up to 91%).During the process, the primary factors influencing product yield and selectivity such as the composition of the catalytic system, stoichiometric ratios of the reagents, temperature, and reaction duration were systematically studied.It was demonstrated that 2,2,2-trifluoroethanol (TFE) serves to break down magnesium acetylide associates, thereby enhancing the reactivity of the in situ formed complex.A reaction mechanism for the alkynylation reaction, based on the cooperative effect of the ligand and the fluorine-containing components, was proposed.The electronic and steric effects of the substituents within the aldehydes were explained based on chemical principles.The structures and purity of the synthesized compounds were confirmed using 1 H, 13 C NMR spectroscopy.

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