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2018/3
Synthesis and antioxidant activity of phenolic derivatives with heterocycles fragments
Chemical sciences

Authors: Stepan V. VOROBYEV graduated from Dmitry Mendeleev University of Chemical Technology of Russia in 2015. He is junior researcher of Chemistry and Technology of Hydrocarbons Research and Educational Center of Gubkin Russian State University of Oil and Gas (National Research University). He is author of 10 scientific publications. E-mail: vorstepan@yandex.ru
Olga V. PRIMEROVA graduated from Gubkin Russian State University of Oil and Gas in 2015. She is postgraduate student of the Department of Organic Chemistry and Petroleum Chemistry of Gubkin Russian State University of Oil and Gas (National Research University). She is author of 35 scientific publications. E-mail: Primerova92@yandex.ru
Ludmila V. IVANOVA graduated from Gubkin Moscow Institute of Petrochemical and Gas Industry in 1983. She is Professor of the Department of Organic Chemistry and Petroleum Chemistry of Gubkin Russian State University of Oil and Gas (National Research University). She is author of more than 100 scientific publications. E-mail: ivanova.l@gubkin.ru
Vladimir N. KOSHELEV graduated from Gubkin Moscow Institute of Petrochemical and Gas Industry in 1975. He is Vice Rector for Academic Affairs, Head of the Department of Organic Chemistry and Petroleum Chemistry of Gubkin Russian State University of Oil and Gas (National Research University). He is author of more than 320 scientific papers in the field of organic and petroleum chemistry. E-mail: koshelev.v@gubkin.ru
Vladimir D. RYABOV graduated from Gubkin Moscow Institute of Petrochemical and Gas Industry. He is Professor of the Department of Organic Chemistry and Petroleum Chemistry of Gubkin Russian State University of Oil and Gas (National Research University). He is author of more than 180 scientific papers in the field of organic and petroleum chemistry. E-mail: 27helga72@mail.ru

Abstract: 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

Index UDK: 547.56; 547.584

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

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