有机化学 ›› 2013, Vol. 33 ›› Issue (11): 2417-2422.DOI: 10.6023/cjoc201305012 上一篇    下一篇

研究简报

离子液体1-甲基咪唑硫酸氢盐催化合成取代吡咯衍生物

吴长春a, 臧洪俊a, 李大庆a, 於年琴a, 程博闻a, 于楷b   

  1. a 天津工业大学环境与化学工程学院 天津改性与功能纤维重点实验室 天津 300387;
    b 铁岭港华燃气有限公司 铁岭 112002
  • 收稿日期:2013-05-13 修回日期:2013-07-06 发布日期:2013-07-19
  • 通讯作者: 臧洪俊 E-mail:chemhong@126.com
  • 基金资助:

    天津市自然科学基金(No. 11JCZDJC21300)资助项目.

1-Methylimidazolium Hydrogen Sulfate: An Efficient Catalyst for the Synthesis of Substituted Pyrroles

Wu Changchuna, Zang Hongjuna, Li Daqinga, Yu Nianqina, Cheng Bowena, Yu Kaib   

  1. a Department of Environmental and Chemistry Engineering, Tianjin Polytechnic University, Tianjin 300387;
    b Ganghua Gas Limited Company, Tieling 112002
  • Received:2013-05-13 Revised:2013-07-06 Published:2013-07-19
  • Supported by:

    Project supported by the Natural Science Foundation of Tianjin City (No. 11JCZDJC21300).

以2,5-己二酮和胺为原料,1-甲基咪唑硫酸氢盐([HMIM]HSO4)作为环境友好型催化剂,甲醇为溶剂,回流条件下,高效地合成了一系列取代吡咯类衍生物,其结构通过1H NMR,FT-IR,质谱和元素分析表征. 考察了催化剂种类和用量对反应的影响,确定了最佳反应条件,并提出了可能的反应机理. 此外,还研究了催化剂的循环使用性能,研究表明[HMIM]HSO4具有很好的催化性能和重复使用性. 该方法具有条件温和、时间短、产率高及催化剂可重复使用等优点.

关键词: 吡咯衍生物, 离子液体, 2,5-己二酮, 胺, 环境友好型催化剂

Using ionic liquid [HMIM]HSO4 as a eco-friendly catalyst, a variety of N-substituted pyrroles were synthesized by the reaction of 2, 5-hexanedione and primary amines in methanol at reflux. The new compounds were characterized by 1H NMR, FT-IR, mass spectra and elemental analysis. The influence of different catalysts and catalyst loading were investigated, and the optimal reaction conditions were then obtained. A possible mechanism was also proposed. Furthermore, the recycling experiment of the catalyst was conducted and the green catalytic system can be recycled for several times with no decreases in yields and reaction rates. The present methodology offers several advantages such as mild conditions, short reaction time, excellent yields, and recyclable catalyst.

Key words: pyrroles, ionic liquid, 2,5-hexanedione, amine, eco-friendly catalyst