有机化学 ›› 2010, Vol. 30 ›› Issue (03): 381-388. 上一篇    下一篇

研究论文

离子液体[TEAPS]HSO4催化“一锅法”合成
2-取代-1H-菲并[9,10-d]咪唑

 郭红云, 李继超, 邵鸿斌   

  1. (浙江工业大学化学工程与材料学院 杭州 310014)
  • 收稿日期:2009-04-24 修回日期:2009-07-13 发布日期:2010-03-28
  • 通讯作者: 郭红云 E-mail:guohy63@163.com
  • 基金资助:

    浙江省教育厅基金(No.200611)

One-Pot Synthesis of 2-Substituted-1H-phenanthro[9,10-d]-
imidazoles Catalyzed by Ionic Liquids [TEAPS]HSO4

Guo Honghun*,Li Jichao,Shao Hongbin   

  1. (College of Chemical Engineering and Material Science, Zhejiang University of Technology, Hangzhou 310014)
  • Received:2009-04-24 Revised:2009-07-13 Published:2010-03-28

在室温离子液体3-(三乙胺基)丙磺酸硫酸氢盐([TEAPS]HSO4)的催化作用下, 由菲醌、醋酸铵和芳香醛“一锅法”合成了一系列2-取代-1H-菲并[9,10-d]咪唑化合物. 实验中考察了投料比、催化剂用量、溶剂、反应时间对反应的影响, 确定了最优反应条件, 给出了可能的反应机理. 此外催化剂可以方便的回收, 且循环使用四次其催化活性并没有显著降低. 目标产物经过了1H NMR, 13C NMR, IR和MS确证表征. 条件温和, 反应时间短, 产率高, 且对环境友好.

关键词: 离子液体, [TEAPS]HSO4, 一锅法, 2-取代-1H-菲并[9,10-d]咪唑

A series of 2-substituted-1H-phenanthro[9,10-d]imidazoles were synthesized by a three-component, one-pot condensation of 9,10-phenanthrenedione, aromatic aldehydes and ammonium acetate using 3-(triethylammonio)propanesulfonic acid hydrosulfate ([TEAPS]HSO4) as a novel acidic ionic liquid catalyst. Effect of the molar ratio, catalyst amount, solvent and reaction time on the yield was investigated. The optimum reaction conditions were determined and the possible mechanism was proposed. Moreover, the catalyst could be recovered conveniently and reused for at least four times without evident loss of activity. The products were identified by 1H NMR, 13C NMR, IR and MS techniques. The present methodology offers several advantages such as milder conditions, shorter reaction time, excellent yields and environmental friendliness.

Key words: ionic liquid, [TEAPS]HSO4, one-pot synthesis, 2-substituted-1H-phenanthro[9,10-d]imidazole

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