Cyclization of (1,2,4,5-tetrazin-3-yl)hydrazones to 3,7-dihydro-1,2,4-triazolo[4,3-b]-1,2,4,5-tetrazines

被引:0
|
作者
S. G. Tolshchina
A. G. Vyakhireva
N. K. Ignatenko
R. I. Ishmetova
I. N. Ganebnykh
P. A. Slepukhin
G. L. Rusinov
机构
[1] Ural Branch of the Russian Academy of Sciences,I. Ya. Postovsky Institute of Organic Synthesis
来源
Russian Chemical Bulletin | 2009年 / 58卷
关键词
3,7-dihydro-1,2,4-triazolo[4,3-; ]-1,2,4,5-tetrazines; 3,6-disubstituted 1,2,4,5-tetrazines; hydrazones; cyclization; ring-chain isomerism; nucleophilic substitution; alkylation;
D O I
暂无
中图分类号
学科分类号
摘要
The intramolecular cyclization of (6-R-1,2,4,5-tetrazin-3-yl)hydrazones of ketones (R is 3,5-dimethylpyrazol-1-yl, 4-methylimidazol-1-yl, or 2-alkylidenehydrazino) giving rise to the previously unknown 3,7-dihydro-1,2,4-triazolo[4,3-b]-1,2,4,5-tetrazines, including spiro compounds, was studied. The reactivity and the yields of the reaction products depend on the structure of the alkylidene fragment and the nature of the substituent in the tetrazine ring.
引用
收藏
页码:1281 / 1290
页数:9
相关论文
共 50 条
  • [21] 1,2,4,5-Tetrazines and Azolo[1,2,4,5]tetrazines: Synthesis and Reactions with Nucleophiles
    Tolshchina, S. G.
    Rusinov, G. L.
    Charushin, V. N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 49 (01) : 66 - 91
  • [22] AN IMPROVED SYNTHESIS OF 3-SUBSTITUTED 1,2,4-TRIAZOLO[4,3-A]PYRIDINES AND 1,2,4-TRIAZOLO[4,3-B]PYRIDAZINES
    BOURGEOIS, P
    CANTEGRIL, R
    CHENE, A
    GELIN, J
    MORTIER, J
    MOYROUD, J
    SYNTHETIC COMMUNICATIONS, 1993, 23 (22) : 3195 - 3199
  • [23] Synthesis and properties of insensitive [1,2,4]triazolo[4,3-b]-1,2,4,5-tetrazine explosives
    Wang, Guilong
    Lu, Tian
    Fan, Guijuan
    Yin, Hongquan
    Chen, Fu-Xue
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (04) : 1663 - 1666
  • [24] SUBSTITUTED 1-(TETRAZOL-5-YL)-4-ARYL-1,4-DIHYDRO-1,2,4,5-TETRAZINES - A NEW SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED 1,2,4,5-TETRAZINES
    BUTLER, RN
    NIBHRADAIGH, P
    MCARDLE, P
    CUNNINGHAM, D
    JOURNAL OF CHEMICAL RESEARCH-S, 1995, (06): : 224 - 225
  • [25] The coordination chemistry of 1,2,4,5-tetrazines
    Kaim, W
    COORDINATION CHEMISTRY REVIEWS, 2002, 230 (1-2) : 127 - 139
  • [26] MASS SPECTROMETRY OF 1,2,4,5-TETRAZINES
    LARSEN, C
    BINDERUP, E
    MOLLER, J
    ACTA CHEMICA SCANDINAVICA, 1967, 21 (10): : 2855 - &
  • [27] PREPARATION OF MESO-3,6-BIS-(1-HYDROXY-1-PHENYLPROPYL)-1,2,4,5-TETRAZINES,( +/-)-3,6-BIS-(1-HYDROXY-1-PHENYLPROPYL)-1,2,4,5-TETRAZINES, MESO-3,6-BIS-(1-HYDROXY-1-PHENYLETHYL)-1,2,4,5-TETRAZINES, ( +/- )-3,6-BIS-(1-HYDROXY-1-PHENYLETHYL)-1,2,4,5-TETRAZINES, AND OPTICALLY ACTIVE FORMS OF 3,6-BIS-(1-HYDROXY-1-PHENYLPROPYL)-1,2,4,5-TETRAZINES AND 3,6-BIS-(1-HYDROXY-1-PHENYLETHYL)-1,2,4,5-TETRAZINES VIA A NEW SYNTHESIS OF 1,2-DIHYDRO-1,2,4,5-TETRAZINES FROM AMIDINES
    FAHEY, JL
    FOSTER, PA
    NEILSON, DG
    BROKENSH.JL
    PETERS, DAV
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (05): : 719 - &
  • [28] 1,2,4,5-Tetrazinyl-Substituted Amino-1,2,4,5-Tetrazines
    Breiner, Megan M.
    Chavez, David E.
    Myers, Thomas W.
    Gilardi, Richard D.
    SYNLETT, 2015, 26 (04) : 557 - 560
  • [29] ENEHYDRAZINES .3. THERMOLYSIS OF 1,2,4,5-TETRAMETHYLHEXAHYDRO-1,2,4,5-TETRAZINES IN MASS SPECTROMETER
    SUCROW, W
    BETHKE
    CHONDROM.G
    TETRAHEDRON LETTERS, 1971, (19) : 1481 - &
  • [30] A one-pot synthesis of [1,2,3]triazino[4,3-b]-[1,2,4,5]tetrazines
    Shawali, AS
    Elghandour, AA
    El-Sheikh, SM
    JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 2000, 342 (01): : 96 - 99