Citation: Lü Xia, Meng Tianzhuo, Zheng Bo, Zhang Yi, Wu Jiajia, Shi Xiaoxin. Synthesis of 1, 1'-Biisoquinolines via Cu-Catalyzed Oxidative Aromatization[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2663-2668. doi: 10.6023/cjoc201704007 shu

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

Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237

Corresponding author: Shi Xiaoxin, xxshi@ecust.edu.cn
Received Date: 8 April 2017
Revised Date: 17 June 2017
Available Online: 4 October 2017
Fund Project: the National Natural Science Foundation of China 20972048Project supported by the National Natural Science Foundation of China (No. 20972048)

Figures(1)

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).
- 1, 1'-biisoquinolines,
- Bischler-Napieralski cyclization,
- copper catalysis,
- oxidation,
- aromatization
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