A convenient synthesis of benzo-1, 2, 3, 4-tetrazine-1, 3-dioxide

被引：0
|
作者：
机构：
[1] Zhang, Wei-Wei
[2] Zhao, Xiu-Xiu
[3] Lin, Zhi-Hui
[4] Pang, Si-Ping
[5] Sun, Cheng-Hui
[6] Li, Sheng-Hua
来源：
Li, S.-H. (lishenghua@bit.edu.cn) | 1600年 / Institute of Chemical Materials, China Academy of Engineering Physics卷 / 21期
关键词：
13C NMR - 3-dioxide - Aqueous ammonia - Heterocycles - Organic Chemistry - Target compound;
D O I：
10.3969/j.issn.1006-9941.2013.04.029
中图分类号：
学科分类号：
摘要：
Benzo-1, 2, 3, 4-tetrazine-1, 3-dioxide was synthesized from 2-bromonitrobenzene, which is converted to 2-bromo-1-(tert-butyl-NNO-azoxy) benzene by a three-step standem reaction. Amination of 2-bromo-1-(tert-butyl-NNO-azoxy) benzene with aqueous ammonia using Cu2O as the catalyst yielded 2-amino-1-(tert-butyl-NNO-azoxy) benzene, that was cyclized with nitration agents N2O5 or NO2BF4 to give benzo-1, 2, 3, 4-tetrazine-1, 3-dioxide. A mild and convenient route was developed. Moreover, the target compound was identified by 1H NMR, 13C NMR, IR, MS-EI and elemental analysis.
引用
收藏
相关论文
共 50 条
  • [1] STRUCTURE OF BENZO-1,2,3,4-TETRAZINE 1,3-DIOXIDE
    YAMAGUCHI, K
    TAKAHASHI, H
    KAIHOH, T
    ITOH, T
    OKADA, M
    NAGATA, K
    MATSUMURA, G
    OHSAWA, A
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1992, 48 : 1237 - 1239
  • [2] Mechanical sensitivity of furazano-1,2,3,4-tetrazine-1,3-dioxide
    V. A. Teselkin
    Combustion, Explosion, and Shock Waves, 2009, 45 : 632 - 633
  • [3] Mechanical Sensitivity of Furazano-1,2,3,4-tetrazine-1,3-dioxide
    Teselkin, V. A.
    COMBUSTION EXPLOSION AND SHOCK WAVES, 2009, 45 (05) : 632 - 633
  • [4] The Synthesis and Energetic Properties of 5,7-Dinitrobenzo-1,2,3,4-tetrazine-1,3-dioxide (DNBTDO)
    Klapoetke, Thomas M.
    Piercey, Davin G.
    Stierstorfer, Joerg
    Weyrauther, Michael
    PROPELLANTS EXPLOSIVES PYROTECHNICS, 2012, 37 (05) : 527 - 535
  • [5] Enthalpy of formation and explosive properties of 5,6-(3,4-furazano)-1,2,3,4-tetrazine-1,3-dioxide
    Pepekin, V. I.
    Matyushin, Yu. N.
    Gubina, T. V.
    RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY B, 2011, 5 (01) : 97 - 100
  • [6] Principles of interaction of furazano-1,2,3,4-tetrazine-1,3-dioxide with organic solvents
    Zelenov, V. P.
    Kalmykov, P. I.
    Kalashnikov, A. I.
    RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A, 2013, 87 (05) : 767 - 771
  • [7] Principles of interaction of furazano-1,2,3,4-tetrazine-1,3-dioxide with organic solvents
    V. P. Zelenov
    P. I. Kalmykov
    A. I. Kalashnikov
    Russian Journal of Physical Chemistry A, 2013, 87 : 767 - 771
  • [8] Enthalpy of formation and explosive properties of 5,6-(3,4-furazano)-1,2,3,4-tetrazine-1,3-dioxide
    V. I. Pepekin
    Yu. N. Matyushin
    T. V. Gubina
    Russian Journal of Physical Chemistry B, 2011, 5
  • [9] Study on the computer-aided design of high energetic compounds based on the 1,2,3,4-tetrazine-1,3-dioxide frame
    Lai, Wei-Peng
    Yu, Tao
    Liu, Ying-Zhe
    Ma, Yi-Ding
    Lian, Peng
    Ge, Zhong-Xue
    Lv, Jian
    JOURNAL OF MOLECULAR MODELING, 2017, 23 (12)
  • [10] Benzo-1,2,3,4-tetrazine 1,3-dioxides: Synthesis and NMR study
    Churakov, AM
    Smirnov, OY
    Ioffe, SL
    Strelenko, YA
    Tartakovsky, VA
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (14) : 2342 - 2349
12345