Bulletin of Taras Shevchenko National University of Kyiv. ChemistryВісник Київського національного університету імені Тараса Шевченка. Хімія |
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METHYL ESTER OF {2-[2-CYANO-2-(4-NITROPHENYL)VINYL]PHENOXY}ACETIC ACID IN REDUCTION PROCESSESKuziv S.Shablykina O., shablykina@ukr.net Khilya V. Taras Shevchenko National University of Kyiv, Kyiv, Ukraine Bulletin of Taras Shevchenko National University of Kyiv. Chemistry. 2017, Volume 2(54), P. 71-73. https://doi.org/10.17721/1728-2209.2017.2(54).14 Because of the very high electrophylity of observed molecule it's unfeasible to obtain good result in reactions with strong nucleophyles or with chemical reduction agents; that's why the hydrogenation in mild condition was used on the first step. It was found that the nitro group and the activated C=C bond were reducted simultaneously by H2 at 1.2 atm presure and room temperature with Pd/C catalizing; so methyl ester of {2-[2-(4-aminophenyl)-2-cyanoethyl]phenoxy}acetic acid was formed. Further hydrogenation took place on higher H2 presure (80 atm); and as a result of the saturation of C≡N bond methyl ester of {2-[3-amino-2-(4-aminophenyl)propyl]phenoxy}acetic acid creation occurred. The last compound can be transformed into 2-{2-[3-amino-2-(4-aminophenyl)propyl]phenoxy}ethanol by the LiAlH4 action. Such interesting structure also can be synthetized through the reduction of 3-[2-(2-hydroxyethoxy)phenyl]-2-(4-nitrophenyl)propionitrile that was obtained earlier: in the first step hydrogenation (1.2 atm H2) produced 3-[2-(2-hydroxyethoxy)phenyl]-2-(4-aminophenyl)propionitrile which nitrile group was reducted by LiAlH4 in the second step. Key words: methyl ester of {2-[2-cyano-2-(4-nitrophenyl)vinyl]phenoxy}acetic acid, 2,3-diarylpropionitrile, 2,3-diarylpropylamine, 2-aryloxyethanol.![]() МЕТИЛОВИЙ ЕСТЕР {1-[2-(4-НІТРОФЕНІЛ)-2-ЦІАНОВІНІЛ]ФЕНОКСИ}ОЦТОВОЇ КИСЛОТИ В РЕАКЦІЯХ ВІДНОВЛЕННЯКузів С.Шабликіна О., shablykina@ukr.net Хиля В. Київський національний університет імені Тараса Шевченка, Київ Вісник Київського національного університету імені Тараса Шевченка. Хімія. 2017, Випуск 2(54), С. 71-73. https://doi.org/10.17721/1728-2209.2017.2(54).14 Ключові слова: метиловий естер {1-[2-(4-нітрофеніл)-2-ціановініл]фенокси}оцтової кислоти, 2,3-діарилпропіонітрил, 2,3-діарилпропіламін, 2-арилоксиетанол.![]() |