有机化学 ›› 2019, Vol. 39 ›› Issue (10): 2843-2850.DOI: 10.6023/cjoc201902030 上一篇    下一篇

研究论文

水相中酸性离子液体功能化β-环糊精催化合成四氢苯并[a]氧杂蒽-11-酮衍生物

刘孝庆a, 王菲a, 孙慧a, 郑梦雅a, 王华兰b, 巩凯a*()   

  1. a 江南大学药学院 无锡 214122
    b 杭州师范大学 有机硅化学及材料技术教育部重点实验室 杭州 311121
  • 收稿日期:2019-02-26 修回日期:2019-04-16 出版日期:2019-10-25 发布日期:2019-06-06
  • 通讯作者: 巩凯 E-mail:gongkai@jiangnan.edu.cn
  • 基金资助:
    国家自然科学基金(51303069);国家自然科学基金(21303036);中央高校基本科研业务费专项资金(JUSRP21940);浙江省重中之重资助项目(ZX15001018)

Synthesis of Tetrahydrobenzo[a]xanthen-11-ones Catalyzed byAcid Ionic Liquid Functionalized β-Cyclodextrin in Water

Liu Xiaoqina, Wang Feia, Sun Huia, Zheng Mengyaa, Wang Hualanb, Gong Kaia*()   

  1. a School of Pharmaceutical Science, Jiangnan University, Wuxi 214122
    b Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education,Hangzhou Normal University, Hangzhou 311121
  • Received:2019-02-26 Revised:2019-04-16 Online:2019-10-25 Published:2019-06-06
  • Contact: Gong Kai E-mail:gongkai@jiangnan.edu.cn
  • Supported by:
    Project supported by the National Natural Science Foundation of China(51303069);Project supported by the National Natural Science Foundation of China(21303036);The Fundamental Research Funds for the Central Universities(JUSRP21940);The Key Disciplines in Zhejiang Province(ZX15001018)

结合β-环糊精和离子液体的优点, 制备了酸性离子液体功能化的β-环糊精(β-CD-AIL), 采用FT-IR, 1H NMR和 13C NMR对其结构进行表征. β-CD-AIL催化芳香醛、β-萘酚和1,3-二羰基化合物合成一系列12-芳基-8,9,10,12-四氢苯并[a]氧杂蒽-11-酮衍生物. 实验结果表明, β-CD-AIL具有良好的催化性能和可循环性能. 该方法具有反应条件温和、反应快、良好产率和操作简单等优点.

关键词: 离子液体, β-环糊精, 多组分反应, 四氢苯并[a]氧杂蒽-11-酮衍生物, 水相反应

Taking advantage of biocompatible β-cyclodextrin (β-CD) and ionic liquid (IL), β-cyclodextrin functionalized with acid ionic liquid (β-CD-AIL) was prepared and characterized by FT-IR, 1H NMR and 13C NMR. β-CD-AIL was evaluated as catalyst for the preparation of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones via one-pot condensation reaction of β-naphthol, aromatic aldehydes and cyclic 1,3-dicarbonyl compounds. The results showed that β-CD-AIL behaved excellent efficiency and recyclability. The key benefits of this protocol involve mild reaction conditions, fast reaction speed, good to excellent yields and simple operational procedure.

Key words: ionic liquid, β-cyclodextrin, multicomponent reactions, tetrahydrobenzo[a] xanthen-11-ones, aqueous media