Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine

被引：29
|
作者：
Tang, Yongxing [1 ]
He, Chunlin [1 ]
Yin, Ping [1 ]
Imler, Gregory H. [2 ]
Parrish, Damon A. [2 ]
Shreeve, Jean'ne M. [1 ]
机构：
[1] Univ Idaho, Dept Chem, Moscow, ID 83844 USA
[2] Naval Res Lab, 4555 Overlook Ave, Washington, DC 20375 USA
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 19期
关键词：
Energetic materials; Nitrogen heterocycles; Azo coupling reaction; Azido group; Imidazole; NITROGEN; COMPOUND; PERFORMANCE; DERIVATIVES;
D O I：
10.1002/ejoc.201800347
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Despite the high potential of the azo-coupled fused tricyclic 1,2,3,4-tetrazine ring system in energetic materials, there are only very limited examples of such a scaffold. The oxidation of di-N-amino compound 1 with tert-butyl hypochlorite (tBuOCl) gives rise to the unexpected chloro-substituted compound 2, which behaves as a precursor to the structurally attractive diazido/nitro-substituted fused tricyclic 1,2,3,4-tetrazine 3. The structure is well characterized and is supported by single-crystal X-ray diffraction. Compound 3 was found to be a highly energetic and sensitive explosive.
引用
收藏
页码：2273 / 2276
页数：4
相关论文
共 50 条
  • [21] Nitration and bromination of benzo-1,2,3,4-tetrazine 1,3-dioxides
    Smirnov, OY
    Churakov, AM
    Strelenko, YA
    Ioffe, SL
    Tartakovsky, VA
    RUSSIAN CHEMICAL BULLETIN, 2002, 51 (10) : 1841 - 1848
  • [22] Nitration and bromination of benzo-1,2,3,4-tetrazine 1,3-dioxides
    O. Yu. Smirnov
    A. M. Churakov
    Yu. A. Strelenko
    S. L. Ioffe
    V. A. Tartakovsky
    Russian Chemical Bulletin, 2002, 51 : 1841 - 1848
  • [23] Nucleophilic substitution in benzo-1,2,3,4-tetrazine 1,3-dioxides
    O. Yu. Smirnov
    A. M. Churakov
    A. Yu. Tyurin
    Yu. A. Strelenko
    S. L. Ioffe
    V. A. Tartakovsky
    Russian Chemical Bulletin, 2002, 51 : 1849 - 1856
  • [24] Mechanism of benzo-1,2,3,4-tetrazine 1-N-oxide formation
    Mendeleev Commun, 1 (22):
  • [25] Mechanism of benzo-1,2,3,4-tetrazine 1-N-oxide formation
    Churakov, AM
    Smirnov, OY
    Strelenko, YA
    Ioffe, SL
    Tartakovskii, VA
    Struchkov, YT
    Dolgushin, FM
    Yanovsky, AI
    MENDELEEV COMMUNICATIONS, 1996, (01) : 22 - 23
  • [26] Nucleophilic substitution in benzo-1,2,3,4-tetrazine 1,3-dioxides
    Smirnov, OY
    Churakov, AM
    Tyurin, AY
    Strelenko, YA
    Ioffe, SL
    Tartakovsky, VA
    RUSSIAN CHEMICAL BULLETIN, 2002, 51 (10) : 1849 - 1856
  • [27] 1,2,3,4-TETRAZINE 1,3-DIOXIDES - A NEW CLASS OF HETEROCYCLIC-COMPOUNDS
    CHURAKOV, AM
    IOFFE, SL
    STRELENKO, YA
    TARTAKOVSKII, VA
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1990, 39 (03): : 639 - 640
  • [28] Benzo-1,2,3,4-tetrazine 1,3-dioxides as new chromophore systems
    Rezchikova, KI
    Churakov, AM
    Burshtein, KY
    Shlyapochnikov, VA
    Tartakovskii, VA
    MENDELEEV COMMUNICATIONS, 1997, (05) : 174 - 175
  • [29] 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
  • [30] Benzo-1,2,3,4-tetrazine 1,3-dioxides annulated with tetraazapentalene systems
    Smirnov, O. Yu.
    Churakov, A. M.
    Strelenko, Yu. A.
    Tartakovsky, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2008, 57 (10) : 2180 - 2184
12345