大学化学 >> 2020, Vol. 35 >> Issue (4): 178-186.doi: 10.3866/PKU.DXHX201910060

所属专题: 全国大学生化学实验创新设计竞赛

  上一篇    

Ugi四组分一锅法高效合成结构独特的活性生物碱化合物

李厚金(), 许阳, 钟云竹, 章笑研, 朱芳, 陈六平   

  • 收稿日期:2019-10-29 录用日期:2019-10-30 发布日期:2019-11-20
  • 通讯作者: 李厚金 E-mail:ceslhj@mail.sysu.edu.cn
  • 基金资助:
    广东省高等教育教学改革项目;中山大学本科教学改革研究项目

Synthesis of Unique Bioactive Alkaloids by Ugi Four-Component One-Pot Reaction

Houjin Li(), Yang Xu, Yunzhu Zhong, Xiaoyan Zhang, Fang Zhu, Liuping Chen   

  • Received:2019-10-29 Accepted:2019-10-30 Published:2019-11-20
  • Contact: Houjin Li E-mail:ceslhj@mail.sysu.edu.cn

摘要:

α-氨基酸、醛、异腈和醇为原料,四组分在室温条件下通过一锅法反应制备得到结构独特的天然活性生物碱1,1’-亚胺基二羧酸衍生物。利用薄层色谱、高效液相色谱-质谱联用仪对反应进程进行监测,用硅胶柱层析对产物进行纯化,化合物的结构通过质谱、核磁共振波谱的解析确定。该反应是Ugi反应的创新发展,具有反应操作简单、产率高、立体选择性好、高原子经济性等特点,在新药设计与合成、组合化学和天然产物合成中具有广泛的应用。

关键词: Ugi反应, 多组分反应, 1, 1’-亚胺基二羧酸衍生物, 生物碱, 一锅法反应

Abstract:

Using α-amino acids, aldehydes, isocyanides and alcohols as the starting materials, four components react in one pot at room temperature to obtain naturally unique bioactive alkaloids, 1, 1'-iminodicarboxylic acid derivatives. The reaction process is monitored by thin layer chromatography and liquid chromatography-mass spectrometry, and the products are purified by silica gel column chromatography. The structures are determined by mass spectrometry and nuclear magnetic resonance spectroscopy. The reaction is an innovative development of Ugi reaction, which has the characteristics of simple reaction operation, high yield, good stereoselectivity and high atomic economy. It has been widely used in the design and synthesis of new drugs, combinatorial chemistry and natural product synthesis.

Key words: Ugi reaction, Multi-component reaction, 1, 1'-iminodicarboxylic acid derivatives, Alkaloid, One-pot reaction

MSC2000: 

  • G64