TY - JOUR
T1 - A convenient synthesis of benzo-1, 2, 3, 4-tetrazine-1, 3-dioxide
AU - Zhang, Wei Wei
AU - Zhao, Xiu Xiu
AU - Lin, Zhi Hui
AU - Pang, Si Ping
AU - Sun, Cheng Hui
AU - Li, Sheng Hua
PY - 2013/8
Y1 - 2013/8
N2 - 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.
AB - 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.
KW - Benzo-1, 2, 3, 4-tetrazine 1, 3-dioxide
KW - Nitrogen-rich heterocycle
KW - Organic chemistry
KW - Synthesis
UR - http://www.scopus.com/inward/record.url?scp=84885648905&partnerID=8YFLogxK
U2 - 10.3969/j.issn.1006-9941.2013.04.029
DO - 10.3969/j.issn.1006-9941.2013.04.029
M3 - Article
AN - SCOPUS:84885648905
SN - 1006-9941
VL - 21
SP - 552
EP - 553
JO - Hanneng Cailiao/Chinese Journal of Energetic Materials
JF - Hanneng Cailiao/Chinese Journal of Energetic Materials
IS - 4
ER -