有机化学 ›› 2018, Vol. 38 ›› Issue (5): 1199-1206.DOI: 10.6023/cjoc201711011 上一篇    下一篇

研究论文

由氰基乙酰芳胺衍生物出发合成喹啉-2,4-二酮类化合物

仲帅帅, 黄鹏, 王兴越, 林觅, 葛春华   

  1. 辽宁大学化学院 沈阳 110036
  • 收稿日期:2017-11-07 修回日期:2017-12-25 发布日期:2018-01-10
  • 通讯作者: 黄鹏,E-mail:huangp019@126.com;葛春华,E-mail:chhge@lnu.edu.cn E-mail:huangp019@126.com;chhge@lnu.edu.cn
  • 基金资助:

    辽宁省博士科研启动基金(No.201601096)和沈阳市科技计划(No.F17-231-1-05)资助项目.

Synthesis of Quinoline-2, 4-diones from Cyanoacetanilide Derivatives

Zhong Shuaishuai, Huang Peng, Wang Xingyue, Lin Mi, Ge Chunhua   

  1. College of Chemistry, Liaoning University, Shenyang 110036
  • Received:2017-11-07 Revised:2017-12-25 Published:2018-01-10
  • Contact: 10.6023/cjoc201711011 E-mail:huangp019@126.com;chhge@lnu.edu.cn
  • Supported by:

    Project supported by the Doctoral Scientific Research Foundation of Liaoning Province (No. 201601096) and the Science and Technology Plan Project of Shenyang City (No. F17-231-1-05).

喹啉-2,4-二酮结构单元广泛存在于天然产物以及具有生物活性的合成化合物中.报道一种通过αα-二烃基氰基乙酰芳胺化合物在三氟甲烷磺酸甲酯作用下的分子内Houben-Hoesch反应合成喹啉-2,4-二酮类化合物的方法.该方法具有适用范围广、操作简便、反应条件温和等优点.

关键词: 喹啉酮, 腈, 甲基化, 环化

Quinoline-2, 4-dione unit is present in many natural products and synthetic compounds along with a broad range of bioactivities. Herein, a new approach to the synthesis of quinoline-2, 4-diones is developed based on a methyl triflate (TfOMe)-promoted intramolecular Houben-Hoesch reaction of α, α-dialkyl substituted cyanoacetanilides. The broad substrate scope, simple operation and mild reaction conditions make this synthetic method very attractive.

Key words: quinolinone, nitrile, methylation, cyclization