高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (11): 2457-2463.doi: 10.7503/cjcu20200340

• 有机化学 • 上一篇    下一篇

酸促进2-乙烯基苯胺与重氮的[5+1]环化合成2-芳基喹啉

南江(), 陈璞, 马养民   

  1. 陕西科技大学化学与化工学院, 中国轻工业轻化工助剂重点实验室, 西安 710021
  • 收稿日期:2020-06-10 出版日期:2020-11-10 发布日期:2020-11-06
  • 通讯作者: 南江 E-mail:nanjiang@sust.edu.cn
  • 基金资助:
    国家自然科学基金(21801159);陕西省自然科学基金(2020JQ-705)

Acid-promoted [5+1] Annulation of 2-Vinylanilines with Diazo Compounds to 2-Arylquinolines

NAN Jiang(), CHEN Pu, MA Yangmin   

  1. College of Chemistry & Chemical Engineering,Key Laboratory of Chemical Additives for China National Light Industry,Shaanxi University of Science and Technology,Xi’an 710021,China
  • Received:2020-06-10 Online:2020-11-10 Published:2020-11-06
  • Contact: NAN Jiang E-mail:nanjiang@sust.edu.cn
  • Supported by:
    Supported by the National Natural Science Foundation of China(21801159);the Natural Science Foundation of Shaanxi Province, China(2020JQ?705)

摘要:

利用廉价易得的2-乙烯基苯胺与重氮化合物在三氟乙酸催化下发生[5+1]环化反应, 以中等至良好的产率合成了24种2-芳基喹啉衍生物. 该方法无需金属催化剂, 官能团兼容性好, 反应成本低, 不仅拓展了重氮化合物参与的新型有机反应, 同时也为2-芳基取代喹啉的合成提供了高效、 经济且简洁的新方法.

关键词: 酸促进[5+1]环化, 无金属催化, 2-芳基喹啉

Abstract:

An acid-promoted [5+1] annulation of 2-vinylanilines with diazo compounds for the synthesis of 2-arylquinolines was developed. The strategy applies cheap and available anilines and diazo compounds as substrates, and generates 24 kinds of 2-arylquinolines in metal-free catalysis with excellent functional group tole-rance in moderate to good yields. This method not only provides an efficient, economical and simple approach for the synthesis of 2-arylquinolines, but also enriches the organic reactions of diazo compounds.

Key words: Acid-promoted [5+1] annulation, Metal-free catalysis, 2-Arylquinoline

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