2-(二硝基亚甲基)-4,5-咪唑烷二酮与甲醇的反应研究  

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

作　　者：蔡华强[1] 舒远杰[1] 黄辉[1] 程碧波[1] 

机构地区：[1]中国工程物理研究院化工材料研究所,绵阳621900

出　　处：《有机化学》2005年第1期90-95,共6页Chinese Journal of Organic Chemistry

基　　金：中国工程物理研究院基金(No. 20020540)资助项目.

摘　　要：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.Low temperature nitration of 2-methylimidazole gave 2-(dinitromethylene)-4,5-imidazolidinedione (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 I 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.

关 键 词：甲醇 FOX-7 硝基 收率 二酮 2-甲基咪唑 开环反应 亚甲基 络合性能 亲核试剂 

分 类 号：O621[理学—有机化学]