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Citation: ZHAO Xuejing, ZHU Jie, LU Ming. Improvement of the Oxidation Process in the Synthesis of 2,6-Diamino-3,5-dinitropyrazine-1-oxide[J]. Chinese Journal of Applied Chemistry, ;2014, 31(1): 41-49. doi: 10.3724/SP.J.1095.2014.30043 shu

Improvement of the Oxidation Process in the Synthesis of 2,6-Diamino-3,5-dinitropyrazine-1-oxide

1.
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China

Corresponding author: LU Ming,
Received Date: 16 January 2013
Available Online: 12 April 2013
Fund Project: 国家自然科学基金委员会-中国工程物理研究院联合基金资助项目(11076017) (11076017)

A new catalytic system was applied to the oxidation reactions involved in the synthesis of 2,6-diamino-3,5-dinitropyrazine-1-oxide(LLM-105),in which protonated peroxotungstate immobilized into the network of cross-linked chitosan with the superparamagnetic Fe₃O₄ core(Fe₃O₄/CS/HWO) was used as the catalyst.With H₂O₂ as the oxidant,good to excellent yields could be achieved with pyrazine,2,6-dimethoxypyrazine,2,6-dichloropyrazine and 2-chloro-6-methoxypyrazine as the substrates without addition of trifluoracetic acid.A representative procedure for the oxidation process is as following:to 30 mL of CH₃CN containing substrate(10 mmol) and Fe₃O₄/CS/HWO(0.1 mmol,about 0.1 g),30% H₂O₂(5 mL) was added dropwisely by 5 times at 60℃ temperature.The oxidation process was monitored by TLC.Product could be obtained with a yield ranging from 60% to 73%.Theoretical studies were also carried out with Gaussian 03 to evaluate the oxidation process.All of the calculated data matched well with the experimental results.
- protonated peroxotungstate,
- oxidation,
- pyrazine derivatives,
- diamino-dinitropyrazine-oxide,
- theoretical studies
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