Copper-Promoted N-Arylation of 8-Acylaminoquinoline Compounds

doi:10.6023/cjoc201710035

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1193-1198.DOI: 10.6023/cjoc201710035 Previous Articles Next Articles

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铜促进的8-酰氨基喹啉类化合物N-芳基化反应

肖祯^a,b, 乐强^a,b, 冉子垚^a,b, 张谦^a,b, 李栋^b

a 湖北省太阳能高效利用协同创新中心武汉 430068;
b 湖北工业大学材料与化学工程学院武汉 430068

收稿日期:2017-10-27 修回日期:2017-12-23 发布日期:2018-01-10
通讯作者: 张谦,E-mail:zhangqian620@hotmail.com;李栋,E-mail:dongli@mail.hbut.edu.cn E-mail:zhangqian620@hotmail.com;dongli@mail.hbut.edu.cn
基金资助:
国家自然科学基金（No.21702054）和太阳能高效利用湖北省协同创新中心开放基金（No.HBSKFQN2016003）资助项目.

Copper-Promoted N-Arylation of 8-Acylaminoquinoline Compounds

Xiao Zhen^a,b, Yue Qiang^a,b, Ran Ziyao^a,b, Zhang Qian^a,b, Li Dong^b

a Hubei Collaborative Innovation Center for High-efficiency Utilization of Solar Energy, Wuhan 430068;
b College of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068

Received:2017-10-27 Revised:2017-12-23 Published:2018-01-10
Contact: 10.6023/cjoc201710035 E-mail:zhangqian620@hotmail.com;dongli@mail.hbut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21702054) and the Open Fund of Hubei Collaborative Innovation Center for High-efficiency Utilization of Solar Energy (No. HBSKFQN2016003).

1. Copper-Promoted N-Arylation of 8-Acylaminoquinoline Compounds.PDF(3802KB)

Abstract

A copper-promoted N-arylation of 8-acylaminoquinolines has been developed. The N-arylation of 8-acylaminoquinoline with triaryl bismuth generated the target products in moderate to high yields under 40 mol% Cu(OAc)₂, 2.0 equiv. of NaHCO₃ in 1, 4-dioxane at 100 ℃ for 12 h. The reaction is compatible with a wide range of quinoline substrates, which provides a new method for synthesis of N-arylamide compounds.

Key words: copper, arylation, 8-acylaminoquinoline, triaryl bismuth

Cite this article

Xiao Zhen, Yue Qiang, Ran Ziyao, Zhang Qian, Li Dong. Copper-Promoted N-Arylation of 8-Acylaminoquinoline Compounds[J]. Chin. J. Org. Chem., 2018, 38(5): 1193-1198.

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[1] Suwanprasop, S.; Nhujak, T.; Roengsumran, S. Ind. Eng. Chen. Res. 2004, 43, 4973.
[2] (a) Edwards, G.; Weston, A. H. Trends Pharmacol. Sci. 1990, 11, 417.
(b) Zhang, Y.-M. Ph.D Dissertation, Tsinghua University, Beijing, 2010 (in Chinese). (张永铭, 博士论文, 清华大学, 北京, 2010.)
[3] (a) Klapars, A.; Antilla, J.-C.; Huang, X.-H.; Buchwald, S.-L. J. Am. Chem. Soc. 2001, 123, 7727.
(b) Antilla, J.-C.; Klapars, A.; Buchwald, S.-L. J. Am. Chem. Soc. 2002, 124, 11684.
(c) Klapars, A.; Buchwald, S.-L. J. Am. Chem. Soc. 2002, 124, 14844.
(d) Shafir, A.; Buchwald, S.-L. J. Am. Chem. Soc. 2006, 128, 8742.
(e) Jones, G.-O.; Liu, P.; Houk, K.-N.; Buchwald, S.-L. J. Am. Chem. Soc. 2010, 132, 6205.
(f) Klapars, A.; Huang, X.-H.; Buchwald, S.-L. J. Am. Chem. Soc. 2002, 124, 7421.
(g) Antilla, J.-C.; Baskin, J.-M.; Barder, T.-E.; Buchwald, S.-L. J. Org. Chem. 2004, 69, 5578.
(h) Job, G.-E.; Buchwald, S.-L. Org. Lett. 2002, 4, 3703.
(i) Jiang, L.; Job, G.-E.; Klapars, A.; Buchwald, S.-L. Org. Lett. 2003, 5, 3667.
(j) Altman, R.-A.; Buchwald, S.-L. Org. Lett. 2007, 9, 643.
(k) Rivero, M.-R.; Buchwald, S.-L. Org. Lett. 2007, 9, 973.
(l) Wolter, M.; Klapars, A.; Buchwald, S.-L. Org. Lett. 2001, 3, 3807.
(m) Kwong, F.-Y.; Klapars, A.; Buchwald, S.-L. Org. Lett. 2002, 4, 581.
(n) Kwong, F.-Y.; Buchwald, S.-L. Org. Lett. 2003, 5, 793.
(o) Altman, R.-A.; Buchwald, S.-L. Org. Lett. 2006, 8, 2779.
(p) Martin, R.-M.; Larsen, C.-H.; Cuenca, A.; Buchwald, S.-L. Org. Lett. 2007, 9, 3379.
(q) Zheng, N.; Buchwald, S.-L. Org. Lett. 2007, 9, 4749.
[4] Chen, C.; Yang, L.-M. J. Org. Chem. 2007, 72, 6324.
[5] (a) Suribabu, J.; Sekarpandi, S.; Laxmidhar, R.; Tathagata, M.; Santu, M.; Tharmalingam, P. J. Org. Chem. 2009, 74, 1971.
(b) Bhosale, M. A.; Bhanage, B. M. RSC Adv. 2014, 4, 15122.
(c) Manirul, I.; Paramita, M.; Kazi, T.; Anupam, S. R.; Sanchita, M.; Dilder, H. J. Organomet. Chem. 2010, 695, 2284.
[6] (a) Ezzat, R.; Ali, A.; Mohammad, J. Tetrahedron Lett. 2016, 52, 219.
(b) Rahul, S.; Bharat, K. A.; Dushyant, S. R.; Krishna, N. S. Tetrahedron 2013, 69, 1038.
[7] (a) Sawant, S. D.; Srinivas, M.; Aravinda Kumar, K. A.; Lakshma Reddy, G.; Singh, P. P.; Singh, B.; Sharma, A. K.; Sharma, P. R.; Vishwakarma, R. A. Tetrahedron Lett. 2013, 54, 5351.
(b) Xu, J.; Li, R. J. Chem. Res. 2012, 36, 381.
[8] Kametani, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2000, 41, 2655.
[9] Li, J.; Ackermann, L. Chem.-Eur. J. 2015, 21, 5718.
[10] (a) Gui, Q.-W.; Chen, X.; Hu, L.; Wang, D.-L.; Liu, J.-D.; Tan, Z. Adv. Synth. Catal. 2016, 358, 509.
(b) Hu, L.; Gui, Q.-W.; Chen, X.; Tan, Z.; Zhu, G.-G. Org. Biomol. Chem. 2016, 14, 11070.
[11] Tinnis, F.; Stridfeldt, E.; Lundberg, H.; Adolfsson, H.; Olofsson, B. Org. Lett. 2015, 17, 2688.
[12] (a) Luan, J.-F.; Zhang, L.-Y.; Hu, Z.-T. Molecules 2011, 16, 4191.
(b) Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683.
(c) Postel, M.; Dunach, E. Coord. Chem. Rev. 1996, 155, 127.
[13] Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021.
[14] Balsane, K. E.; Gund, S. H.; Nagarkar, J. M. Catal. Commun. 2017, 89, 29.
[15] Hébert, M.; Petiot, P.; Benoit, E.; Dansereau, J.; Ahmad, T.; Roch, A.-L.; Ottenwaelder, X.; Gagnon, X. J. Org. Chem. 2016, 81, 5401.
[16] Muriel Hall, D. J. Chem. Soc. 1948, 1603.

铜促进的8-酰氨基喹啉类化合物N-芳基化反应

Copper-Promoted N-Arylation of 8-Acylaminoquinoline Compounds

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