Effect of the nature of a fluorinated substituent on the synthesis of functionalized 1,3-diketones

被引：9
作者：
Kudyakova, Yu S. [1 ]
Onoprienko, A. Ya [1 ,2 ]
Edilova, Yu O. [1 ,2 ]
Burgart, Ya, V [1 ,2 ]
Saloutin, V., I [1 ,2 ]
Bazhin, D. N. [1 ,2 ]
机构：
[1] Russian Acad Sci, I Ya Postovsky Inst Organ Synth, Ural Branch, 22-20 Ul S Kovalevskoi, Ekaterinburg 620108, Russia
[2] Ural Fed Univ, 19 Ul Mira, Ekaterinburg 620002, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2021年 / 70卷 / 04期
基金：
俄罗斯科学基金会;
关键词：
fluorinated; 1; 3-diketones; Claisen condensation; acetals; transition metal diketonates; COMPLEXES; ORGANOFLUORINE; PYRAZOLES; EFFICIENT; PACKING; ACETALS;
D O I：
10.1007/s11172-021-3145-z
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis of alkali metal and copper(ii) 1-polyfluoroalkyl-4,4-dimethoxypentane-1,3-dionates is reported. The subsequent treatment of these compounds with oxalic acid or ethylenediaminetetraacetic acid disodium salt affords functionalized 1,3-diketones. The nature of the polyfluoroalkyl substituent was found to affect the conditions of the Claisen condensation and the stability of the acetal group in acidic medium.
引用
收藏
页码：745 / 752
页数：8
相关论文
共 37 条
  • [1] Organic and hybrid systems: from science to practice
    Ananikov, Valentine P.
    Eremin, Dmitry B.
    Yakukhnov, Sergey A.
    Dilman, Alexander D.
    Levin, Vitalij V.
    Egorov, Mikhail P.
    Karlov, Sergey S.
    Kustov, Leonid M.
    Tarasov, Andrei L.
    Greish, Aleksandr A.
    Shesterkina, Anastasiya A.
    Sakharov, Alexey M.
    Nysenko, Zinaida N.
    Sheremetev, Aleksei B.
    Stakheev, Aleksandr Yu.
    Mashkovsky, Igor S.
    Sukhorukov, Alexey Yu.
    Ioffe, Sema L.
    Terent'ev, Alexander O.
    Vil', Vera A.
    Tomilov, Yury V.
    Novikov, Roman A.
    Zlotin, Sergei G.
    Kucherenko, Alexander S.
    Ustyuzhanina, Nadezhda E.
    Krylov, Vadim B.
    Tsvetkov, Yury E.
    Gening, Marina L.
    Nifantiev, Nikolay E.
    [J]. MENDELEEV COMMUNICATIONS, 2017, 27 (05) : 425 - 438
  • [2] Spin transition characteristics of molecular solvates of CuII complexes with nitroxides: sensitivity to the packing type
    Artiukhova, N. A.
    Romanenko, G., V
    Letyagin, G. A.
    Bogomyakov, A. S.
    Tolstikov, S. E.
    Ovcharenko, V. I.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2019, 68 (04) : 732 - 742
  • [3] Intramolecular cyclization of lithium 4,4-dimethoxy-1-(perfluoroalkyl)pentane-1,3-dionates on treatment with boron trifluoride diethyl etherate
    Bazhin, D. N.
    Kudyakova, Yu. S.
    Burgart, Ya. V.
    Saloutin, V. I.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2018, 67 (03) : 497 - 499
  • [4] Dinuclear lanthanide-lithium complexes based on fluorinated β-diketonate with acetal group: magnetism and effect of crystal packing on mechanoluminescence
    Bazhin, Denis N.
    Kudyakova, Yulia S.
    Bogomyakov, Artem S.
    Slepukhin, Pavel A.
    Kim, Grigory A.
    Burgart, Yanina V.
    Saloutin, Victor I.
    [J]. INORGANIC CHEMISTRY FRONTIERS, 2019, 6 (01): : 40 - 49
  • [5] Dinuclear copper(II) complex with novel N,N′,N",O-tetradentate Schiff base ligand containing trifluoromethylpyrazole and hydrazone moieties
    Bazhin, Denis N.
    Kudyakova, Yulia S.
    Slepukhin, Pavel A.
    Burgart, Yanina V.
    Malysheva, Natalia N.
    Kozitsina, Alisa N.
    Ivanova, Alla V.
    Bogomyakov, Artem S.
    Saloutin, Victor I.
    [J]. MENDELEEV COMMUNICATIONS, 2018, 28 (02) : 202 - 204
  • [6] Synthesis and tuberculostatic activity of functionalized pyrazoles derived from (trifluoromethyl)pyrazole containing a hydrazone group
    Bazhin, Denis N.
    Kudyakova, Yulia S.
    Onoprienko, Aleksandra Ya.
    Slepukhin, Pavel A.
    Burgart, Yanina V.
    Saloutin, Victor I.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (12) : 1324 - 1329
  • [7] Detrifluoroacetylation of 4,4,4-trifluoro-3,3-dihydroxy-2-(hydroxyimino)butan-1-ones as a convenient synthetic strategy for acyl cyanides
    Bazhin, Denis N.
    Kudyakova, Yulia S.
    Nemytova, Natalia A.
    Burgart, Yanina V.
    Saloutin, Victor I.
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2016, 186 : 28 - 32
  • [8] A Convenient Approach to CF3-Containing N-Heterocycles Based on 2-Methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one
    Bazhin, Denis N.
    Kudyakova, Yulia S.
    Roeschenthaler, Gerd-Volker
    Burgart, Yanina V.
    Slepukhin, Pavel A.
    Isenov, Maksim L.
    Saloutin, Victor I.
    Charushin, Valery N.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (23) : 5236 - 5245
  • [9] A concise approach to CF3-containing furan-3-ones, (bis)pyrazoles from novel fluorinated building blocks based on 2,3-butanedione
    Bazhin, Denis N.
    Chizhov, Dmitry L.
    Roeschenthaler, Gerd-Volker
    Kudyakova, Yulia S.
    Burgart, Yanina V.
    Slepukhin, Pavel A.
    Saloutin, Victor I.
    Charushin, Valery N.
    [J]. TETRAHEDRON LETTERS, 2014, 55 (42) : 5714 - 5717
  • [10] Catalyst-free transformations of diethyl 2-ethoxymethylenemalonate and diethyl polyfluorobenzoylmalonates in water
    Bazhin, Denis N.
    Kudyakova, Yulia S.
    Burgart, Yanina V.
    Saloutin, Victor I.
    [J]. TETRAHEDRON LETTERS, 2012, 53 (15) : 1961 - 1963
1234