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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (01): 90-95. 上一篇    下一篇

研究论文

2-(二硝基亚甲基)-4,5-咪唑烷二酮与甲醇的反应研究

蔡华强*，舒远杰，黄辉，程碧波   

  1. (中国工程物理研究院化工材料研究所 绵阳 621900)
  • 收稿日期:2004-03-02 修回日期:2004-08-30 发布日期:2004-12-30
  • 通讯作者: 蔡华强

Study on Reaction of 2-(Dinitromethylene)-4,5-imidazolidinedione with Methanol

CAI Hua-Qiang*,SHU Yuan-Jie,HUANG Hui,CHENG Bi-Bo   

  1. (Institute of Chemical Materials, China Academy of Engineering Physics, Mianyang 621900)
  • Received:2004-03-02 Revised:2004-08-30 Published:2004-12-30
  • Contact: CAI Hua-Qiang

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1886

被引次数

10

以2-甲基咪唑为原料合成2-(二硝基亚甲基)-4,5-咪唑烷二酮(1), 收率为33.9% (16.8%文献值), 首次采用低碳液态醇实现1的开环反应, 产物为FOX-7. 对反应条件进行了优化, 对比了甲醇、甲酸、氨水三种亲核试剂的开环效果, 开环试剂为甲醇时, FOX-7收率为94.6%, 高于文献值(87.4%). 研究了1的络合性能, 合成了1的甲醇加合物2并进行了结构表征. 对开环反应机理和乙二酰脲的形成机理进行了探讨.

关键词: 1,1-二氨基-2,2-二硝基乙烯(FOX-7), 反应机理, 甲醇, 开环, 2-(二硝基亚甲基)-4,5-咪唑烷二酮, 加合物

Low temperature nitration of 2-methylimidazole gave 2-(dinitromethylene)-4,5-imidazolidine-dione (1) in 33.9% yield (16.8% in literature). Ring cleavage of 1 to FOX-7 was achieved by liquid alcohols for the first time and reaction conditions were optimized. The effect of methanol, formic acid and aqueous ammonia as nucleophiles on the ring cleavage of 1 was investigated. It was found that methanol was a better nucleophile than other alcohols with 94.6% yield of FOX-7 (87.4% in literature). Methanol adduct 2, the first adduct of 1, was synthesized and characterized. The reaction mechanisms of ring cleavage and parabanic acid formation were discussed.

Key words: methanol, 1,1-diamino-2,2-dinitroethylene (FOX-7), reaction mechanism, ring cleavage, 2-(dinitrome-
thylene)-4,5-imidazolidinedione, adduct