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

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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.
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