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

页码：1841 / 1848

页数：8

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