Nitration and bromination of benzo-1,2,3,4-tetrazine 1,3-dioxides

被引：12
|
作者：
Smirnov, OY [1 ]
Churakov, AM [1 ]
Strelenko, YA [1 ]
Ioffe, SL [1 ]
Tartakovsky, VA [1 ]
机构：
[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2002年 / 51卷 / 10期
关键词：
benzo-1,2,3,4-tetrazines; N-oxides; nitration; bromination; dibromoisocyanuric acid;
D O I：
10.1023/A:1021344300420
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Benzo-1,2,3,4-tetrazine 1,3-dioxide (BTDO) and its derivatives were nitrated with HNO3/H2SO4 or HNO3/oleum and brominated with dibromoisocyanuric acid in CF3CO2H/H2SO4 (5 : 1) or H2SO4. The reactivity of positions in the benzene ring of this heterocyclic system as regards electrophilic substitution was found to change in the following order: 5 approximate to 7 > 8 > 6. Mono- and dinitro-BTDOs and mono- and polybromo-BTDOs were synthesized. Their structures were confirmed by H-1, C-13, and N-14 NMR spectra.
引用
收藏
页码：1841 / 1848
页数：8
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