Nickel-Catalyzed C-H Halogenation of 8-Aminoquinolines for the Synthesis of C(5) and C(7) Di-halogenated Quinolines
- Corresponding author: Hao Wenyan, wenyanhao@jxnu.edu.cn Liu Yunyun, chemliuyunyun@jxnu.edu.cn
Citation:
Hao Wenyan, Wang Yuyun, Yang Guomin, Liu Yunyun. Nickel-Catalyzed C-H Halogenation of 8-Aminoquinolines for the Synthesis of C(5) and C(7) Di-halogenated Quinolines[J]. Chinese Journal of Organic Chemistry,
;2017, 37(10): 2678-2684.
doi:
10.6023/cjoc201704049
(a) Kouznetsov, V. V. ; Mendez, L. Y. ; Gomez, C. M. Curr. Org. Chem. 2005, 9, 141.
(b) Michael, J. P. Nat. Prod. Rep. 2008, 25, 166.
(c) Tokoro, Y. ; Nagai, A. ; Kokado, K. ; Chujo, Y. Macromolecules 2009, 42, 2988.
(d) Solomon, V. R. ; Lee, H. Curr. Med. Chem. 2011, 18, 1488.
(e) Liu, G. ; Yi, M. ; Liu, L. ; Wang, J. ; Wang, J. Chem. Commun. 2015, 51, 2911.
(a) Madrid, P. B. ; Sherrill, J. ; Liou, A. P. ; Weisman, J. L. ; Derisi, J. L. ; Guy, R. K. Bioorg. Med. Chem. Lett. 2005, 15, 1015.
(b) Tardito, S. ; Barilli, A. ; Bassanetti, I. ; Tegoni, M. ; Bussolati, O. ; Franchi-Gazzola, R. ; Mucchino, C. ; Marchio, L. J. Med. Chem. 2012, 55, 10448.
(c) Abouelhassan, Y. ; Garrison, V. G. ; Burch, M. ; Wong, W. ; Norwood, V. M. ; Huigens, R. W. Bioorg. Med. Chem. Lett. 2014, 24, 5076.
(d) Vippagunta, S. R. ; Dorn, A. ; Matile, H. ; Bhattacharjee, A. K. ; Karle, J. M. ; Ellis, W. Y. ; Ridley, R. G. ; Vennerstrom, J. L. J. Med. Chem. 1999, 42, 4630.
(e) Bhat, S. ; Shim, J. S. ; Zhang, F. ; Chong, C. R. ; Liu, J. O. Org. Biomol. Chem. 2012, 10, 2979.
(f) Borchardt, R. T. J. Med. Chem. 1973, 16, 382.
(g) Liu, Y. -C. ; Wei, J. -H. ; Chen, Z. -F. ; Liu, M. ; Gu, Y. -Q. ; Huang, K. -B. ; Li, Z. -Q. ; Liang, H. Eur. J. Med. Chem. 2013, 69, 554.
(a) Jiang, H. ; Taggart, H. ; Zhang, X. ; Benbrook, D. M. ; Lind, S. E. ; Ding, W. -Q. Cancer Lett. 2011, 312, 11.
(b) Heidary, D. K. ; Howerton, B. S. ; Glazer, E. C. J. Med. Chem. 2014, 57, 8936.
(a) Sun, K. ; Lv, Y. ; Wang, J. ; Sun, J. ; Liu, L. ; Jia, M. ; Liu, X. ; Z. Li, Z. ; Wang, X. ; Org. Lett. 2015, 17, 4408.
(b) Wasa, M. ; Worrell, B. T. ; Yu, J. Q. Angew. Chem. , Int. Ed. 2010, 49, 1275.
(c) Tobisu, M. ; Hyodo, I. ; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070.
(d) Berman, A. M. ; Lewis, J. C. ; Bergman, R. G. ; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 14926.
(e) Zhao, D. ; Wang, W. ; Yang, F. ; Lan, J. ; Yang, L. ; Gao, G. ; You, J. Angew. Chem. , Int. Ed. 2009, 48, 3296.
(a) Boudet, N. ; Lachs, J. R. ; Knochel, P. Org. Lett. 2007, 9, 5525.
(b) Kwak, J. ; Kim, M. ; Chang, S. J. Am. Chem. Soc. 2011, 133, 3780.
(c) Chen, Q. ; du Jourdin, X. M. ; Knochel, P. J. Am. Chem. Soc. 2013, 135, 4958.
(d) Tsai, C. -C. ; Shih, W. -C. ; Fang, C. -H. ; Li, C. -Y. ; Ong, T. -G. ; Yap, G. P. J. Am. Chem. Soc. 2010, 132, 11887.
(a) Guo, H. ; Chen, M. ; Jiang, P. ; Chen, J. ; Pan, L. ; Wang, M. ; Xie, C. ; Zhang, Y. Tetrahedron 2015, 71, 70.
(b) Xu, J. ; Zhu, X. ; Zhou, G. ; Ying, B. ; Ye, P. ; Su, L. ; Shen, C. ; Zhang, P. Org. Biomol. Chem. 2016, 14, 3016.
(c) Liu, X. X. ; Wu, Z, Y. ; Luo, X. L. ; He, Y, Q. ; Zhou, X, Q. ; Fan, Y. X. ; Huang. G. S. RSCAdv. 2016, 6, 71485.
For selected example, (a) Zhang, J. ; Chen, T. ; Yang, J. ; Han, L. Chem. Commun. 2015, 51, 7540.
(b) Li, X. ; Feng, Z. ; Jiang, Z. ; Zhang, X. Org. Lett. 2015, 17, 5570.
(c) Li, K. ; Wu, Q. ; Lan, J. ; You, J. Nat. Commun. 2015, 6, 8404.
(d) Jin, L. ; Wan, L. ; Feng, J. ; Cai, C. Org. Lett. 2015, 17, 4726.
(a) Cho, C. S. ; Lee, J. W. ; Lee, D. Y. ; Shim, S. C. ; Kim, T. J. Chem. Commun. 1996, 2115.
(b) Nogi, K. ; Fujihara, T. ; Terao, J. ; Tsuji, Y. J. Org. Chem. 2015, 80, 11618.
(c) Tjutrins, J. ; Shao, J. ; Yempally, V. ; Bengali, A. A. ; Arndtsen, B. A. Organometallics 2015, 34, 1802.
(d) Lo, W. ; Hu, C. ; Berenson, T. ; Tracer, N. ; Shlian, D. ; Khaloo, M. ; Benhaim, A. ; Jiang, J. Chem. Commun. 2015, 51, 9432.
(e) Hoshimoto, Y. ; Ohata, T. ; Sasaoka, Y. ; Ohashi, M. ; Ogoshi, S. J. Am. Chem. Soc. 2014, 136, 15877.
(a) Ohashi, M. ; Kishizaki, O. ; Ikeda, H. ; Ogoshi, S. J. Am. Chem. Soc. 2009, 131, 9160.
(b) Sato, Y. ; Saito, N. ; Mori, M. J. Am. Chem. Soc. 2000, 122, 2371.
(c) Yeh, C. H. ; Korivi, R. P. ; Cheng, C. H. Angew. Chem. , Int. Ed. 2008, 47, 4892.
(d) Stolley, R. M. ; Duong, H. A. ; Thomas, D. R. ; Louie, J. J. Am. Chem. Soc. 2012, 134, 15154.
(e) Thakur, A. ; Facer, M. E. ; Louie, J. Angew. Chem. , Int. Ed. 2013, 52, 12161.
Zhan, B.-B.; Liu, Y.-H.; Hu, F.; Shi, B.-F. Chem. Commun. 2016, 52, 4934.
doi: 10.1039/C6CC00822D
(a) Hao, W. Y. ; Tian, J. ; Li, W. ; Shi, R. ; Huang, Z. ; Lei. A. W. Chem. Asian J. 2016, 11, 1664.
(b) Wan, J. -P. ; Li, Y. ; Liu, Y. Org. Chem. Front. 2016, 3, 768.
(c) Liu, Y. ; Huang, M. ; Wei, L. Asian J. Org. Chem. 2017, 6, 41.
He, Y.; Zhao, N.; Qiu, L.; Zhang, X.; Fan, X. Org. Lett. 2016, 18, 6054.
doi: 10.1021/acs.orglett.6b02998
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