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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (10): 1803-1806. 上一篇    下一篇

研究简报

10-苄基吖啶酮的合成及其与硼氢化钠还原反应研究

高春梅a ; 刘华臣a; 蒋宇扬*,a ; 谭春燕a ; 曹德榕*,b   

  1. (a广东省化学生物学重点实验室 清华大学深圳研究生院 深圳 518055)
    (b华南理工大学化学科学学院 广州 510640)
  • 收稿日期:2008-01-21 修回日期:2008-03-19 发布日期:2008-10-20
  • 通讯作者: 蒋宇扬*;曹德榕*

Synthesis of 10-Benzyl-9-acridone and Its Reduction with NaBH4

GAO, Chun-Meia ; LIU, Hua-Chena; JIANG, Yu-Yang*,a ;
TAN, Chun-Yana ; CAO, De-Rong*,b
  

  1. (a Key Laboratory of Chemical Biology of Guangdong Province, the Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055)
    (b College of Chemistry, South China University of Technology, Guangzhou 510640)
  • Received:2008-01-21 Revised:2008-03-19 Published:2008-10-20
  • Contact: JIANG, Yu-Yang*;CAO, De-Rong*

PDF

1485

被引次数

15

合成了一系列的10-苄基吖啶酮类化合物, 并探讨了一种用硼氢化钠氢化还原吖啶酮制备10-苄基-9,10-二氢吖啶的简便方法. 吖啶酮1与氯化苄及其衍生物2在氢化钠/N,N-二甲基甲酰胺/碘化钾中反应高产率生成10-苄基吖啶酮类化合物3; 3经硼氢化钠氢化还原生成10-苄基-9,10-二氢吖啶类化合物4, 产率88%～96%. 反应中没有得到预期的产物10-苄基-9,10-二氢吖啶醇类化合物4’, 其反应机理可能是3首先被硼氢化钠还原成醇中间体4’, 4’在硼氢化钠存在下不稳定, 迅速地被进一步还原成4.

关键词: 9, 吖啶, 10-二氢吖啶, 硼氢化钠, 吖啶酮

A series of 10-benzyl-9-acridones were synthesized and their reduction with NaBH4 to 10-benzy1-9,10-dihydroacridine derivatives was developed. Acridone 1 reacted with benzyl chlorides 2 in NaH/DMF/KI to give 10-benzyl-9-acridones 3 in high yields. Subsequent reduction of 3 with NaBH4 gave 10-benzy1-9,10-dihydroacridine derivatives 4 with yields of 88%～96%. However, the expected 10-benzy1-9,10-dihydro-9-hydroxyacridine derivatives 4’ were not detected. Probably, 4’ is the first reduc-tion product, which is not stable and reduced to 4 by NaBH4 immediately.

Key words: acridone, 9,10-dihydroacridine, NaBH4, acridine