Synthesis and transformations of cyanomethyl-1,2,4,5-tetrazines

被引:6
|
作者
Tolshchina, S. G. [1 ]
Ishmetova, R. I. [1 ]
Ignatenko, N. K. [1 ]
Korotina, A. V. [1 ]
Slepukhin, P. A. [1 ]
Rusinov, G. L. [1 ]
Charushin, V. N. [1 ]
机构
[1] Russian Acad Sci, Ural Branch, I Ya Postovskii Inst Organ Synth, Ekaterinburg 620041, Russia
基金
俄罗斯基础研究基金会;
关键词
CH acids; cyanomethyltetrazine anions; ethyl cyanoacetate; 3,6-dihetaryl-1,2,4,5-tetrazines; 1,3-indanedione; malonodinitrile; pyrrolo[1,2-b][1,2,4,5]tetrazines; tetrazine coordination compounds; nucleophilic substitution; TETRAZINES; 3,6-BIS(3,5-DIMETHYL-4-R-PYRAZOL-1-YL)-1,2,4,5-TETRAZINES; 1,2,4,5-TETRAZINES;
D O I
10.1007/s10593-013-1288-z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Derivatives of s-tetrazine containing malonodinitrile, ethyl cyanoacetate, and 1,3-indanedione fragments were synthesized by the nucleophilic substitution of heterocyclic groups in 3,6-diazolyl-1,2,4,5-tetrazines. Coordination compounds of the cyanomethyltetrazine anion with Cu+, Mn2+, and the tetrathiafulvalene radical cation were obtained, and their structures were determined. A transformation of cyanomethyltetrazines to pyrrolo[1,2-b][1, 2, 4, 5]tetrazines catalyzed by metal cations was discovered.
引用
收藏
页码:604 / 617
页数:14
相关论文
共 50 条
  • [31] SYNTHESIS AND MESOMORPHIC PROPERTIES OF SOME DISUBSTITUTED UNSYMMETRICAL PHENYL-1,2,4,5-TETRAZINES
    HUDSON, CM
    NEUBERT, ME
    LACKNER, AM
    MARGERUM, JD
    SHERMAN, E
    LIQUID CRYSTALS, 1995, 19 (06) : 871 - 881
  • [32] Synthesis and tuberculostatic activity of amine-substituted 1,2,4,5-tetrazines and pyridazines
    R. I. Ishmetova
    N. K. Ignatenko
    I. N. Ganebnykh
    S. G. Tolschina
    A. V. Korotina
    M. A. Kravchenko
    S. N. Skornyakov
    G. L. Rusinov
    Russian Chemical Bulletin, 2014, 63 : 1423 - 1430
  • [33] Synthesis of 5-trifluoromethylpyrazol-1-yl-substituted 1,2,4,5-tetrazines
    S. G. Tolshchina
    N. K. Ignatenko
    P. A. Slepukhin
    R. I. Ishmetova
    G. L. Rusinov
    Chemistry of Heterocyclic Compounds, 2010, 46 : 691 - 698
  • [34] CHEMISTRY OF HEXAHYDRO-1,2,4,5-TETRAZINES .1. PREPARATION AND CHARACTERIZATION OF METHYL- AND PHENYL-SUBSTITUTED HEXAHYDRO-1,2,4,5-TETRAZINES
    JENSEN, KA
    HAMMERUM, S
    ACTA CHEMICA SCANDINAVICA, 1972, 26 (03): : 1258 - &
  • [35] SYNTHESIS OF 5-TRIFLUOROMETHYLPYRAZOL-1-YL-SUBSTITUTED 1,2,4,5-TETRAZINES
    Tolshchina, S. G.
    Ignatenko, N. K.
    Slepukhin, P. A.
    Ishmetova, R. I.
    Rusinov, G. L.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (06) : 691 - 698
  • [36] Synthesis and Characterization of 3,6-di(nitramino)-1,2,4,5-tetrazines
    Rudakov, G. F.
    Ustinova, T. V.
    Zhilin, V. F.
    THEORY AND PRACTICE OF ENERGETIC MATERIALS (VOL IX), PROCEEDINGS OF THE 2011 INTERNATIONAL AUTUMN SEMINAR ON PROPELLANTS, EXPLOSIVES AND PYROTECHNICS, 2011, : 3 - 7
  • [37] [4+2] Cycloaddition reactions of 1,2,4,5-tetrazines with allylcarboranes
    Rusinov, G. L.
    Ishmetova, R. I.
    Tolshchina, S. G.
    Ignatenko, N. K.
    Ganebnykh, I. N.
    Slepukhin, P. A.
    Ol'shevskaya, V. A.
    Kalinin, V. N.
    Charushin, V. N.
    RUSSIAN CHEMICAL BULLETIN, 2010, 59 (01) : 116 - 121
  • [38] Synthesis, Structures of some Unsymmetrical 3,6-Disubstituted-1,2,4,5-Tetrazines
    Hu, Wei-Xiao
    Xu, Feng
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (06) : 1745 - 1750
  • [39] Improved Synthesis and Thermochemical Properties of Amino- and Hydrazino-1,2,4,5-Tetrazines
    Tat’yana S. Kon’kova
    Yurii N. Matyushin
    Evgeniy А. Miroshnichenko
    Nadezhda V. Palysaeva
    Aleksei B. Sheremetev
    Chemistry of Heterocyclic Compounds, 2020, 56 : 1449 - 1453
  • [40] Improved Synthesis and Thermochemical Properties of Amino- and Hydrazino-1,2,4,5-Tetrazines
    Kon'kova, Tat'yana S.
    Matyushin, Yurii N.
    Miroshnichenko, Evgeniy A.
    Palysaeva, Nadezhda V.
    Sheremetev, Aleksei B.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (11) : 1449 - 1453