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
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