«Proceedings of Gubkin University»

SYNTHESIS AND ANTIOXIDANT ACTIVITY OF PHENOLIC DERIVATIVES WITH HETEROCYCLES FRAGMENTS

UDC: 547.56; 547.584
DOI: -

Authors:

¹ Gubkin Russian State University of Oil and Gas (National Research University, Leninskiy рrospect, 65, 119991, Moscow, Russian Federation

Keywords: organic synthesis, heterocyclic phenols derivatives, quantum-chemical calculations, antioxidant activity

Annotation:

The synthesis of 2-(2,3-dihydroxybenzyl)-1H-isoindol-1,3(2H)-dione was descri-bed. The structure of synthesized compound was confirmed by IR- and NMR-spectroscopy. The way of electrophilic attack of catechol ring depends on the solvent, as it was shown by quantum-chemical calculations (Gaussian09 program, semi-empirical method PM6). In case of substitution at the third position in catechol ring the energy of cationic intermediate is lower in chloroform than the one in methanol. As the reaction proceeds on the way of energy minimum, it afforded the 3-substituted product. Energy of dissociation of ArO-H bond was calculated to reveal possible antioxidant activity of target compounds using quantum chemical method (semi-empirical PM6). The ability of synthesized compounds to destruct cumene hydroperoxide was studied. It was estimated, that 2-(2,3-dihydroxybenzyl)-1H-isoindol-1,3(2H)-dione, 1-(4-hydroxy-5-isopropil-2-methylbenzyl)azepan-2-one and 1-(4-hydroxy-5-isopropil-2-methylbenzyl)pyr-rolidin-2-one possess the best antioxidant effect.

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