高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (11): 2411-2418.doi: 10.7503/cjcu20180326

• 有机化学 • 上一篇    下一篇

纳米氧化铜催化一锅法合成β-咔啉类化合物

张金1,2(), 史天彩1, 罗力文1, 刘佳1, 刘荣1, 刘乐1, 梁明1, 马养民1,2()   

  1. 1. 陕西科技大学化学与化工学院, 西安710021
    2. 陕西省轻化工助剂重点实验室, 西安710021
  • 收稿日期:2018-04-26 出版日期:2018-11-10 发布日期:2018-08-23
  • 作者简介:联系人简介: 张 金, 男, 博士, 副教授, 主要从事功能小分子合成方面的研究. E-mail: zhangjin@sust.edu.cn; 马养民, 男, 博士, 教授, 博士生导师, 主要从事天然产物提取、 合成及鉴定方面的研究. E-mail: mym63@sina.com
  • 基金资助:
    陕西省教育厅专项科研计划项目(批准号: 17JK0107)、 陕西科技大学博士科研启动基金(批准号: BJ12-26)和陕西科技大学大学生创新创业训练计划项目(批准号: 2016102)资助.

One-pot Synthesis of β-Carboline Derivatives Catalyzed by CuO Nanoparticles

ZHANG Jin1,2,*(), SHI Tiancai1, LUO Liwen1, LIU Jia1, LIU Rong1, LIU Le1, LIANG Ming1, MA Yangmin1,2,*()   

  1. 1. College of Chemistry & Chemical Engineering, Shaanxi University of Science and Technology, Xi’an 710021, China
    2. Shaanxi Key Laboratory of Chemical Additives for Industry, Shaanxi University of Science and Technology, Xi’an 710021, China
  • Received:2018-04-26 Online:2018-11-10 Published:2018-08-23
  • Contact: ZHANG Jin,MA Yangmin E-mail:zhangjin@sust.edu.cn;mym63@sina.com
  • Supported by:
    † Supported by the Scientific Research Project of Shaanxi Province Education Department, China(No.17JK0107), the Foundation for Young Scholars of Shaanxi University of Science & Technology, China(No.BJ12-26) and the Training Programs of Innovation and Entrepreneurship for Undergraduates of Shaanxi University of Science and Technology, China(No.2016102).

摘要:

通过纳米氧化铜催化色氨酸酯与醛的环化-氧化串联反应, 发展了一种快速有效合成1,3-二取代-β-咔啉衍生物的一步合成法. 在温和的条件下, 目标产物可以达到中等到优良的产率. 该反应的特点是纳米氧化铜既作为催化剂促进成环, 又作为氧化剂将四氢-β-咔啉氧化成β-咔啉, 从而提高了反应效率.

关键词: 纳米氧化铜, β-咔啉;, Pictet-Spengler反应, 一锅法合成

Abstract:

Compounds containing β-carboline moiety have a variety of special biochemical and pharmacological activities. In order to explore the method for efficient synthesize β-carbolines, a novel method applied Pictet-Spengler cyclization and coupling oxidation in one-step was studied. Tryptophan esters and aromatic aldehydes were heated in N,N-Dimethylformamide via the promotion of nano CuO. Twenty-five compounds of 1,3-disubstituted-β-carbolines were obtained in moderate to excellent yield with subsequent isolation and purification. Attractive features of this method included simple operation, high efficiency and mild condition. Especially, nano CuO as catalyst and oxidant promoted cyclization and oxidation processes in creating β-carbolines motif.

Key words: Nano CuO, β-Carboline derivative;, Pictet-Spengler reaction, One-pot synthesis

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