有机化学 ›› 2019, Vol. 39 ›› Issue (2): 566-570.DOI: 10.6023/cjoc201805024 上一篇    下一篇

研究简报

CuCl2催化“一锅法”合成2-苄基-3,4-二氢异喹啉-1-酮类衍生物

付超, 樊彦霞, 孙启辉, 易维银, 易封萍   

  1. 上海应用技术大学香料香精技术与工程 上海 201418
  • 收稿日期:2018-05-10 修回日期:2018-07-24 发布日期:2018-09-05
  • 通讯作者: 易封萍 E-mail:yifengping@sit.edu.cn

One-Pot Synthesis of 2-Benzyl-3,4-dihydro-2H-isoquinolin-1-ones Catalyzed by CuCl2

Fu Chao, Fan Yanxia, Sun Qihui, Yi Weiyin, Yi Fengping   

  1. School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 201418
  • Received:2018-05-10 Revised:2018-07-24 Published:2018-09-05
  • Contact: 10.6023/cjoc201805024 E-mail:yifengping@sit.edu.cn

成功开发了一种简便、有效地由铜催化"一锅法"合成2-苄基-3,4-二氢异喹啉-1-酮类化合物的方法.该方法以四氢异喹啉、苄基叠氮、含取代基的苯甲醛为原料,经过亲核加成并进一步氧化反应,一锅法合成目标化合物,且目标化合物产率为50%~70%.同时,进一步探究了催化剂的种类、添加剂的种类、反应温度、投料比等因素对反应的影响.结果表明,在CuCl2为催化剂,CH3COOH为添加剂,甲苯为溶剂的条件下,可高效地得到一系列2-苄基-3,4-二氢异喹啉-1-酮类化合物.

关键词: 氯化铜, 一锅法, 2-苄基-3,4-二氢异喹啉-1-酮

An facile, effective, copper-catalyzed one-pot approach to 2-benzyl-3,4-dihydroquinolin-1-ones has been successfully developed. The compounds were achieved by the reaction of tetrahydroisoquinoline, benzyl azide and benzaldehyde in one-pot fashion via nucleophilic addition reaction followed by oxidation. The desired products were afforded in the high yield of 50%~70%. Moreover, The effects of different catalyst, additives, reaction temperature and proportion of substrates on the reaction were also investigated. The results showed that the optimizing conditions of reaction were CuCl2 as catalyst, CH3COOH as additive and toluene as solvent. A series of 2-benzyl-3, 4-dihydro-2H-isoquinolin-1-ones can be efficiently obtained under the optimizing conditions.

Key words: CuCl2, one-pot, 2-benzyl-3,4-dihydro-2H-isoquinolin-1-ones