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化学学报
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化学学报 ›› 2006, Vol. 64 ›› Issue (11): 1145-1150. 上一篇    下一篇

研究论文

功能化离子液体为载体液相合成二氢吡啶酮衍生物

易封萍*,1,2，彭延庆1，宋恭华*,1   

  1. (1华东理工大学药学院药物化工研究所 上海 200237)
    (2上海应用技术学院生物与食品工程系 上海 200235)
  • 投稿日期:2005-05-26 修回日期:2006-02-15 发布日期:2006-06-15
  • 通讯作者: 易封萍

Solution Phase Synthesis of Dihydropyridones Derivatives Using Functionalized Ionic Liquid as Support

YI Feng-Ping*,1,2, PENG Yan-Qing1, SONG Gong-Hua*,1   

  1. (1 Institute of Pesticides & Pharmaceuticals, Department of Pharmacy, East China University of Science and Technology, Shanghai 200237)
    (2 Department of Biotechnology & Food Processing Engineering, Shanghai Institute of Technology, Shanghai 200235)
  • Received:2005-05-26 Revised:2006-02-15 Published:2006-06-15
  • Contact: YI Feng-Ping

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740

被引次数

33 | 6

在微波辐照条件下, 以甲基咪唑、氯乙醇和四氟硼酸钠为原料制备了含羟基功能化离子液体1-(2-羟乙基)-3-甲基咪唑四氟硼酸盐([2-hydemim][BF4]), 并以其为液态载体, 首先与乙酰乙酸乙酯反应, 得到的中间体再分别和Meldrum酸、醋酸铵以及各种芳香醛反应, 最后在温和的条件下用甲醇钠进行切割反应, 得到了一系列产率和纯度较高的3,4-二氢吡啶酮衍生物, 目标化合物不需要进一步的色谱纯化处理, 纯度为95%～98%, 产率为83%～93%. 回收得到的功能化离子液体可以重复套用至少6次也不影响其活性. 表明该方法是一种高效的3,4-二氢吡啶酮衍生物的组合化学合成方法.

关键词: 功能化离子液体, 二氢吡啶酮, 组合化学, 组合合成, 载体

Hydroxyl functionalized ionic liquid 1-(2-hydroxyethyl)-3-methylimidazolium tetrafluoroborate ([2-hydemim][BF4]) was prepared under microwave irradiation via methylimidazolium, chlorohydrin and sodium tetrafluoroborate as materials. A microwave-assisted solution phase parallel synthesis of 3,4-dihydropyridones was developed using hydroxyl functionalized ionic liquid (IL) as soluble support. Firstly, the [2-hydemim][BF4] was reacted with ethyl acetoacetate to obtained IL-bound acetoacetate, then this intermediate was reacted with Meldrum acid, ammonium acetate and aromatic aldehyde. Finally 3,4-dihydropyridone derivatives were obtained in good yields and high purities without chromatographic purification after mild cleavage with sodium methoxide in methanol at room temperature, the purity of the target compounds was 95%～98%, and the yield was 83%～93%. The recovered functionalized ionic liquid could be recycled at least six times without losing its activity. It was clear that the solution-phase synthesis using functionalized ionic liquid as supports could be used in the combinatorial chemistry synthesis of 3,4-dihydropyridones derivatives in high efficiency.

Key words: functionalized ionic liquid, dihydropyridone, combinatorial chemistry, parallel synthesis, support