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

doi:10.6023/cjoc201704007

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

ARTICLE

通过铜催化氧化芳构化合成1,1'-联异喹啉

吕霞, 孟天卓, 郑波, 张义, 吴家家, 施小新

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 E-mail:xxshi@ecust.edu.cn
基金资助:
国家自然科学基金（No.20972048）资助项目.

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

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

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 E-mail:xxshi@ecust.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No.20972048).

1. Synthesis of 1,1'-Biisoquinolines via Cu-Catalyzed Oxidative Aromatization.PDF(899KB)

Abstract

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

Cite this article

Lü Xia, Meng Tianzhuo, Zheng Bo, Zhang Yi, Wu Jiajia, Shi Xiaoxin. Synthesis of 1,1'-Biisoquinolines via Cu-Catalyzed Oxidative Aromatization[J]. Chin. J. Org. Chem., 2017, 37(10): 2663-2668.

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[1] (a) Dai, L.; Zhou, Z.; Zhang, Y.; Ni, C.; Zhang, Z.; Zhou, Y. J. Chem. Soc., Chem. Commun. 1987, 1760.
(b) Maeda, K.; Matsuyama, Y.; Isozaki, K..; Yamada, S.; Mori, Y. J. Chem. Soc., Perkin Trans. 21996, 121.
(c) Yu, W.-Y.; Fung, W.-H.; Zhu, J.-L.; Cheung, K.-K.; Ho, K.-K.; Che, C.-M. J. Chin. Chem. Soc. 1999, 46, 341.
(d) Ashby, M. T.; Alguindigue, S. S.; Schwane, J. D.; Daniel, T. A. Inorg. Chem. 2001, 40, 6643.
(e) Nakajima, M.; Saito, M.; Uemura, M.; Hashimoto, S. Tetrahedron Lett. 2002, 43, 8827.
(f) Glazer, E. C.; Tori, Y. Angew. Chem., Int. Ed. 2002, 41, 4022.
(g) Frediani, P.; Giannelli, C.; Salvini, A.; Ianelli, S. J. Organomet. Chem. 2003, 667, 197.
(h) Zhao, Q.; Liu, S.; Shi, M.; Wang, C.; Yu, M.; Li, L.; Li, F.; Yi, T.; Huang, C. Inorg. Chem. 2006, 45, 6152.
(i) Durola, F.; Sauvage, J.-P.; Wenger, O. S. Chem. Commun. 2006, 171.
(j) Durola, F.; Hanss, D.; Roesel, P.; Sauvage, J.-P.; Wenger, O. S. Eur. J. Org. Chem. 2007, 125.
[2] (a) Case, F. H. J. Org. Chem. 195217, 471.
(b) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80.
(c) Chang, Y. M.; Lee, S. H.; Cho, M. Y.; Yoo, B. W.; Rhee, H. J.; Lee, S. H.; Yoon, C. M. Synth. Commun. 2005, 35, 1851.
(d) Schwab, P. F. H.; Fleiscker, F.; Michl, J. J. Org. Chem. 2002, 67, 443.
(e) Malkov, A. V.; Westwater, M.-M.; Gutnov, A., Ramirez-Lopez, P.; Friscourt, F.; Kadlcikova, A.; Hodacova, J.; Rankovic, Z.; Kotora, M.; Kocovsky, P. Tetrahedron 2008, 64, 11335.
(f) Kammer, S.; Kelling, A.; Baier, H.; Mickler, W.; Dosche, C.; Rurack, K.; Kapp, A.; Lisdat, F.; Holdt, H.-J. Eur. J. Inorg. Chem. 2009, 4648.
[3] (a) Nielsen, A. T. J. Org. Chem. 1970, 35, 2498.
(b) Yao, Q. J.; Khong, D. T.; Gao, Q.; Judeh, Z. M. A. Synthesis 2014, 46, 1793.
[4] (a) Bischler, A.; Napieralski, B. Chem. Ber. 1893, 26, 1903.
(b) Whaley, W. M.; Govindachari, T. R. In Organic Reactions, Ed.:Adams, R., John Wiley and Sons, New York, 1951, Vol. VI, p. 74.
(c) Zhu, R.; Xu, Z.; Ding, W.; Liu, S.; Shi, X.; Lu, X. Chin. J. Chem. 2014, 32, 1039.
[5] Kuo, C.-Y.; Wu, M.-J.; Liu, C.-C. Eur. J. Med. Chem. 2010, 45, 55.
[6] (a) Qi, G.; Ji, Y. Q.; Judeh, Z. M. A. Tetrahedron 2010, 66, 4195.
(b) Siegfried, V. M.-A.; Hilpert, H.; Rey, M.; Dreiding, A. S. Helv. Chim. Acta 1980, 63, 938.
[7] (a) Roding, M. J.; Seo, H.; Hirsch-Weil, D.; Abboud, K. A.; Hong, S. Tetrahedron:Asymmetry 2011, 22, 1097.
(b) Blay, G.; Fernandez, I.; Maco-Aleixandre, A.; Pedro, J. R. Tetrahedron:Asymmetry 2005, 16, 1207.
(c) Li, X.; Chen, X.-Y.; Yuan, Q.-L.; Zhang, D.-F.; Huang, B.-T. Chin. J. Org. Chem. 2006, 26, 1100(in Chinese). (李选, 陈晓影, 袁荞龙, 张丹枫, 黄葆同, 有机化学, 2006, 26, 1100.)

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通过铜催化氧化芳构化合成1,1'-联异喹啉

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

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