Особенности структурного разнообразия 1,3,4,6-тетракарбонильных соединений, их аналогов и азотсодержащих производных (обзор)

Автор: Карманова Ольга Геннадьевна, Козьминых Владислав Олегович, Муковоз Петр Петрович, Козьминых Елена Николаевна

Журнал: Вестник Южно-Уральского государственного университета. Серия: Химия @vestnik-susu-chemistry

Статья в выпуске: 24 (283), 2012 года.

Бесплатный доступ

Обобщены литературные данные и приводятся новые сведения, касающиеся синтеза, структурного разнообразия и свойств 1,3,4,6-тетракарбонильных соединений. бис-1,3-дикетонаты в твердом состоянии представлены (E,E)-изомером, а в растворе преобладающим (Е,Е)- и минорным (Z,Z)-изомерами. Обсуждаются структурные особенности и масс-фрагментация 1,6-диалкил-3,4-дигидрокси-2,4-гексадиен- 1.6-дионов. Конденсацией алкилметилкетонов с диэтилоксалатом и 1,2-диаминобензолом получены 2,3-бис-(2-оксоалкилиден)тетрагидро-1,2,3,4-тетрагидрохиноксалины. С помощью спектральных методов выявлены изомерные формы полученнх соединений. Соединения, содержащие сближенные 1,2- и 1,3- диоксофрагменты, являются перспективными для тонкого органического синтеза и структурного химического анализа.

Еще

Оксалильная конденсация, таутомерные формы, алкилметилкетоны, 6-диалкил-3, 4-дигидрокси-1, 6-гексадиен- 1.6-дионы, бис-1, 3-дикетонаты, 3-бис-оксоилиден-1, 6-тетрагидрохиноксалины

Короткий адрес: https://sciup.org/147160230

IDR: 147160230

Список литературы Особенности структурного разнообразия 1,3,4,6-тетракарбонильных соединений, их аналогов и азотсодержащих производных (обзор)

Schmidt, P.F. Reduktionsprodukte des Oxalyldiacetophenons/P.F. Schmidt//Berichte. -1895. -Bd. 28. -P. 1206-1212.
Claisen, L. Über die Einwirkung des Oxaläthers auf Acetophe/L. Claisen//Berichte. -1887. -Bd. 20. -P. 2188-2189.
Synthesis and structural diversity of 1,6-dialkyl-3,4-dihydroxy-2,4-hexadiene-1,6-diones/O.G. Karmanova, V.O. Kozminykh, P.P. Mukovoz, E.N. Kozminykh//Vestnik Uzno-Ural’skogo gosudarstvennogo universiteta. Seriâ, Himiâ. -2012. -in press. (in Russian)
Synthesis and structural diversity of 1,6-dialkyl-3,4-dihydroxy-2,4-hexadiene-1,6-diones/O.G. Karmanova, V.O. Kozminykh, P.P. Mukovoz, E.N. Kozminykh//Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. -2012. -in press, Registry Number 4413. (in Russian)
Kozminykh, V.O. Claisen condensation of methyl ketones with dialkyloxalates in the synthesis of biologically active carbonyl compounds (review, part 3)/V.O. Kozminykh, V.I. Goncharov, E.N. Kozminykh//Vestnik. Orenburg State University. -2007. -No. 5 (69). -P. 138-148. (in Russian)
Synthesis and antimicrobial activity of 2-substituted 5-aryl-2,3-dihydro-3-furanones and 1,6-diaryl-3,4-dihydroxy-2,4-hexadiene-1,6-diones/V.O. Kozminykh, N.M. Igidov, E.N. Kozminykh et al.//Journal of Pharmaceutical Chemistry. -1991. -Vol. 25, No. 12. -P. 43-47. (in Russian)
Kozminykh, V.O. 1,3,4,6-Tetracarbonyl compounds. A. The novel synthesis of 1,6-diaryl-3,4-dihydroxy-2,4-hexadiene-1,6-diones from 5-aryl-2,3-furandiones/V.O. Kozminykh, L.O. Konshina, N.M. Igidov//J. prakt. Chem. (Chem.-Ztg.). -1993. -Vol. 335, No. 8. -P. 714-716.
1,3,4,6-tetracarbonyl compounds. 3. Synthesis, structural features and antimicrobial activity of 1,6-diaryl-3,4-dihydroxy-2,4-hexadiene-1,6-diones/N.M. Igidov, E.N. Kozminykh, O.A. Sofyina et al.//Chemistry of Heterocyclic Compounds. -1999. -No. 11. -P. 1466-1475. (in Russian)
Kozminykh, V.O. 1,3,4,6-Tetracarbonyl systems. Part 9. Diethyl ketipinate: synthesis, structural features and reaction with 1,2-diaminobenzene/V.O. Kozminykh, P.P. Mukovoz, E.A. Kirillova//Vestnik. Orenburg State University. -2009. -No. 5. -P. 155-166. (in Russian)
Kirillova, E.A. Synthesis, chain tautomerism and ring-chain interconversion of substituted 2,4-dihydroxy-2,4-alkadiene-1,6-diones/E.A. Kirillova, V.O. Kozminykh//Vestnik Uzno-Ural’skogo gosudarstvennogo universiteta. Seriâ, Himiâ. -2009. -No. 23 (156). -P. 9-15. (in Russian)
Synthesis, structural features and tautomerism of 1,6-disubstituted 3,4-dihydroxy-2,4-hexadiene-1,6-diones/E.A. Kirillova, P.P. Mukovoz, A.N. Vinogradov et al.//Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. -2011. -Vol. 54, No. 4. -P. 18-22. (in Russian)
Mukovoz, P.P. Synthesis and structural features of the 3,4-dihydroxy-1,6-hexanedione acid esters/P.P. Mukovoz, O.N. Dvorskaya, V.O. Kozminykh//Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. -2011. -Vol. 54, No. 5. -P. 96-100. (in Russian)
1,3,4,6-Tetracarbonyl compounds. IV. The interaction of 3,4-dihydroxy-2,4-hexadiene-1,6-diones with hydrazine and arylhydrazines/T.M. Shironina, N.M. Igidov, E.N. Kozminykh et al.//Journal of Organic Chemistry. -2001. -Vol. 37, No. 10. -P. 1555-1563. (in Russian)
Kozminykh, V.O. 1,3,4,6-Tetracarbonyl compounds. VI. Synthesis of esters and amides of -substituted 6-aryl-3,4-dihydroxy-6-oxo-2,4-hexadiene acids/V.O. Kozminykh, N.M. Igidov, Y.S. Kasatkina//Journal of Organic Chemistry. -2001. -Vol. 37, No. 11. -P. 1604-1609. (in Russian)
Kozminykh, V.O. Claisen condensation of methyl ketone with dialkyl oxalates in the synthesis of biologically active carbonyl compounds (review, part 3)/V.O. Kozminykh, V.I. Goncharov, E.N. Kozminykh//Vestnik. Orenburg State University. -2007. -No. 5 (69). -P. 138-148. (in Russian)
New modified method of synthesis of 1,6-dialkyl substituted 3,4-dihydroxy-1,6-hexadiene-1,6-diones/O.G. Karmanova, S.S. Zykova, P.P. Mukovoz, V.O. Kozminykh//International Scientific Periodical «Modern Fundamental And Applied Researches». -2011. -No. 3. -P. 106-109. (in Russian)
Synthesis and structural features of 1,6-dialkyl substituted 1,3,4,6-tetraoxohexanes/O.G. Karmanova, S.S. Zykova, V.O. Kozminykh, P.P. Mukovoz//Collected works of the V International scientific practical conference «Nauchnoye tvorchestvo XXI veka». Krasnoyarsk. -2012. -Vol. 3. -P. 264-269. (in Russian)
Karmanova, O.G. Synthesis and chromato-mass spectrometry of 1,6-dialkyl-3,4-dihydroxy-2,4-hexadiene-1,6-diones/O.G. Karmanova, V.O. Kozminykh, P.P. Mukovoz//Collected works of the International scientific practical conference «Voprosy estestvennykh nauk: biologiya, khimiya, fizika», Novosibirsk. -2012. -P. 95-102. (in Russian)
Metal derivatives of p-π-electron-donating polycarbonyl systems with close α-and β-dioxofragments. Part 1. Reference review/V.O. Kozminykh, E.A. Kirillova, Y.V. Shcherbakov et al.//Vestnik. Orenburg State University. -2008. -No. 9 (91). -P. 185-198. (in Russian)
Metal derivatives of p-π-electron-donating poly carbonyl systems with segmented α-and β-dioxofragments. Part 2. Synthesis and structure of the sodium enolates of 1,3-dicarbonyl compound oxyderivatives/V.O. Kozminykh, P.P. Mukovoz, E.A. Kirillova et al.//Vestnik. Orenburg State University. -2009. -No. 1 (95). -P. 128-140. (in Russian)
Kirillova, E.A. Synthesis and structural features of the aryl-substituted sodium oxo enolates and bis-1,3-diketonates/E.A. Kirillova, V.O. Kozminykh//The proceedings of the All-Russian scientific practical conference with international participation «Aktual'nye problemy khimii i metodiki eyo prepodavaniya». Nizhny Novgorod. -2009. -P. 157-160. (in Russian)
Kirillova, E.A. Synthesis and structure of sodium enol derivatives with activated mono-and bis-1,3-dicarbonyl unit/E.A. Kirillova, V.O. Kozminykh//Collected works of the 10th International conference «Aktual'nye problemy sovremennoy nauki. Estestvennye nauki. Chast 8. Organicheskaya khimiya». Samara. -2009. -P. 15-19. (in Russian)

Еще

Статья научная