高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

新法合成乙炔型维A酸

李治章1, 顾峥2, 张荣2, 吴运东2, 王小勇1, 蒋海明1, 向建南2

  

    1. 湖南科技学院化学系, 永州 425100;
    2. 湖南大学化学传感与计量学国家重点实验室, 长沙 410082
  • 收稿日期:2008-06-24 修回日期:1900-01-01 出版日期:2009-03-10 发布日期:2009-03-10
  • 通讯作者: 向建南

New Method for the Preparation of Acetylenic Retinoids

LI Zhi-Zhang1, GU Zheng2, ZHANG Rong2, WU Yun-Dong2, WANG Xiao-Yong1, JIANG Hai-Ming1, XIANG Jian-Nan2*   

    1. Department of Chemistry, Hunan University of Science and Engineering, Yongzhou 425100, China;
    2. State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China
  • Received:2008-06-24 Revised:1900-01-01 Online:2009-03-10 Published:2009-03-10
  • Contact: XIANG Jian-Nan

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被引次数

6

摘要： 合成了一种新型乙炔型维A酸类化合物, 拓展了该类碘代芳香羧酸与苯乙炔直接偶联的无铜 Sonogashira 反应. 以对溴苯甲酸为底物, 研究了无铜条件下PdCl2(PPh3)2的催化性能, 在10倍量的哌啶中, 对溴苯甲酸、苯乙炔和摩尔分数为4%的PdCl2(PPh3)2在85 ℃下反应20 min得到99%的偶联分离产率, 总收率72%. 本方法也适用于相关乙炔型RAs 分子的合成, 具有操作简单、产率高等优点.

关键词: 乙炔型维A 酸, Sonogashira 反应, PdCl2(PPh3)2催化剂

Abstract: Acetylenic RAs is a kind of important drug for treating cancer. In this paper, a novel acetylenic retinoids was synthesized and a directly copper-free Sonogashira coupling between iodoaryl acid and phenylacetylene was developed. In the absence of Cu(Ⅰ), the catalytic coupling of haloaryl carboxylic acids or unactivated aryl bromides with terminal alkynes were shown to occur in the presence of 10 multiple piperidine at 85 ℃ within 20 min with PdCl2(PPh3)2 as catalyst in good yields. The overall yield was 72%. Due to the fact that the reaction is simple and the yield is high, it is applicable to synthesis of other acetylenic RAs.

Key words: Acetylenic retinoids, Sonogashira reaction, PdCl2(PPh3)2 catalyst

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