Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (10): 2663-2668.DOI: 10.6023/cjoc201704007 Previous Articles     Next Articles



吕霞, 孟天卓, 郑波, 张义, 吴家家, 施小新   

  1. 华东理工大学药学院上海市化学生物学重点实验室 上海 200237
  • 收稿日期:2017-04-08 修回日期:2017-06-17 发布日期:2017-07-04
  • 通讯作者: 施小新
  • 基金资助:


Synthesis of 1,1'-Biisoquinolines via Cu-Catalyzed Oxidative Aromatization

Lü Xia, Meng Tianzhuo, Zheng Bo, Zhang Yi, Wu Jiajia, Shi Xiaoxin   

  1. Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237
  • Received:2017-04-08 Revised:2017-06-17 Published:2017-07-04
  • Contact: 10.6023/cjoc201704007
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.20972048).

A new method for practical synthesis of 1,1'-biisoquinolines is described. Treatment of N,N'-diphenethyloxal-amides (1a~1j) with phosphoryl trichloride in acetonitrile or toluene under N2 at reflux produced 3,3',4,4'-tetrahydro-1,1'-biisoquinolines (2a~2j) via Bischler-Napieralski cyclization. Subsequently, compounds 2a~2j underwent Cu(OAc)2-catalyzed aerobic oxidative aromatization in dimethyl sulfoxide (DMSO) in the presence of a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to afford a series of 1,1'-biisoquinolines (3a~3j) in 70%~88% overall yields (2 steps).

Key words: 1,1'-biisoquinolines, Bischler-Napieralski cyclization, copper catalysis, oxidation, aromatization