8-氨基喹啉C(5)位C-H键官能化研究进展

doi:10.6023/cjoc201703020

摘要/Abstract

8-氨基喹啉是存在于天然产物和药物分子中的一种重要含氮芳香杂环化合物；可作为有机配体或者双齿导向基团参与一系列有机合成反应，在材料领域也有着广泛应用，因而，受到越来越多的研究者青睐.近年来通过对喹啉母环结构进行位置选择性修饰，构建单取代及多取代喹啉取得了飞速发展.本综述较全面地总结近年来通过碳氢活化方法构建C（5）位取代8-氨基喹啉衍生物的进展，对该领域所存在的问题和局限性进行了总结，并对今后的发展作出展望.

关键词: 碳氢键活化, 8-氨基喹啉, 远程活化, 8-氨基喹啉5位

8-Aminoquinolines are important nitrogen-containing heterocycles widely existing in the natural products, bio-active molecules and agrochemicals. It has been developed as significant bidentate directing groups or as ligand auxiliary in various kinds of organic reactions, especially in the area of C-H bond functionalization. Therefore, the synthesis of such motifs, especially those with substituted quinolines is of great significance. This review focuses on the remote C-H bond functionalizaitons of 8-aminoquinolines on the C(5) position, including the advantages and disadvantages as well as an outlook in this field.

Key words: C-H bond functionalization, 8-aminoquinoline, remote C-H activation, C(5) position of aminoquinoline

引用此文

朱龙志, 曹鑫, 李优, 刘婷, 王勰, 邱仁华, 尹双凤. 8-氨基喹啉C(5)位C-H键官能化研究进展[J]. 有机化学, 2017, 37(7): 1613-1628.

Zhu Longzhi, Cao Xin, Li You, Liu Ting, Wang Xie, Qiu Renhua, Yin ShuangFeng. Recent Advances on the C-H Bond Functionalization on C(5) Position of 8-Aminoquinolines[J]. Chin. J. Org. Chem., 2017, 37(7): 1613-1628.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] (a) Michael, J. P. Nat. Prod. Rep. 2008, 25, 166.
(b) Kaur, K.; Jain, M.; Reddy, R. P.; Jain, R. Eur. J. Med. Chem. 2010, 45, 3245.
(c) Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles:Structures, Reactions, Synthesis, and Applications, 3rd, John Wiley & Sons, New York, 2013.
(d) Colomb, J.; Becker, G.; Fieux, S.; Zimmer, L.; Billard, T. J. Med. Chem. 2014, 57, 3884.
(e) Tekwani, B. L.; Walker, L. A. Curr. Opin. Infect. Dis. 2006, 19, 623.
[2] (a) Fahrni, C. J.; O'Halloran, T. V. J. Am. Chem. Soc. 1999, 121, 11448.
(b) Huang, J.; Xu, Y.; Qian, X. Dalton. Trans. 2014, 43, 5983.
(c) McQuade, L. E.; Lippard, S. J. Inorg. Chem. 2010, 49, 7464.
(d) Zhu, S. S.; Lin, W. Y.; Yuan, L. Dyes Pigm. 2013, 99, 465.
[3] Peters, W. J. R. Soc. Med. 1999, 92, 345.
[4] Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
[5] (a) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726.
(b) Corbet, M.; De Campo, F. Angew. Chem., Int. Ed. 2013, 52, 9896.
(c) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org. Chem. Front. 2015, 2, 1107.
(d) Daugulis, O.; Roane, J.; Tran, L. D. Acc. Chem. Res. 2015, 48, 1053.
(e) Castro, L. C. M.; Chatani, N. Chem. Lett. 2015, 44, 410.
(f) Liu, J.; Chen, G.; Tan, Z. Adv. Synth. Catal. 2016, 358, 1174.
(g) Rit, R. K.; Yadav, M. R.; Ghosh, K.; Sahoo, A. K. Tetrahedron 2015, 71, 4450.
(h) Zhang, B.; Guan, H.; Liu, B.; Shi, B. Chin. J. Org. Chem. 2014, 34, 1487(in Chinese). (张博, 管晗曦, 刘斌, 史炳锋, 有机化学, 2014, 34, 1487.)
(i) Luo, F.; Long, Y.; Li, Z.; Zhou, X. Acta Chim. Sinica 2016, 74, 805(in Chinese). (罗飞华, 龙洋, 李正凯, 周向葛, 化学学报, 2016, 74, 805.)
[6] (a) Qiu, R.; Reddy, V. P.; Iwasaki, T.; Kambe, N. J. Org. Chem. 2015, 80, 367.
(b) Zhu, L.; Cao, X.; Qiu, R.; Iwasaki, T.; Reddy, V. P.; Xu, X.; Yin, S.-F.; Kambe, N. RSC Adv. 2015, 5, 39358.
(c) Reddy, V. P.; Qiu, R. H.; Iwasaki, T.; Kambe, N. Org. Lett. 2013, 15, 1290.
(d) Su, L.; Dong, J.; Liu, L.; Sun, M.; Qiu, R.; Zhou, Y.; Yin, S.-F. J. Am. Chem. Soc. 2016, 138, 12348.
[7] (a) Wang, X.; Qiu, R.; Yan, C.; Reddy, V. P.; Zhu, L.; Xu, X.; Yin, S.-F. Org. Lett. 2015, 17, 1970.
(b) Wang, X.; Zhu, L.; Chen, S.; Xu, X.; Au, C. T.; Qiu, R. Org. Lett. 2015, 17, 5228.
(c) Zhu, L.; Qiu, R.; Cao, X.; Xiao, S.; Xu, X.; Au, C. T.; Yin, S.-F. Org. Lett. 2015, 17, 5528.
(d) Reddy, V. P.; Qiu, R.; Iwasaki, T.; Kambe, N. Org. Biomol. Chem. 2015, 13, 6803.
[8] (a) Marco-Contelles, J.; Pérez-Mayoral, E.; Samadi, A.; Carreiras, M. d. C.; Soriano, E. Chem. Rev. 2009, 109, 2652.
(b) Sudharshan, M.; Zehra, T.; Sanjay, B. Curr. Org. Chem. 2008, 12, 1116.
(c) Reitsema, R. H. Chem. Rev. 1948, 43, 43.
(d) Bergstrom, F. W. Chem. Rev. 1944, 35, 153.
(e) Kouznetsov, V. V.; Méndez, L. Y. V.; Gómez, C. M. M. Curr. Org. Chem. 2005, 9, 141.
(f) Kong, L. K.; Zhou, Y. Y.; Huang, H.; Yang, Y.; Liu, Y. Y.; Li, Y. Z. J. Org. Chem. 2015, 80, 1275.
(g) Wang, Y.; Chen, C.; Peng, J.; Li, M. Angew. Chem., Int. Ed. 2013, 52, 5323.
(h) Horn, J.; Marsden, S. P.; Nelson, A.; House, D.; Weingarten, G. G. Org. Lett. 2008, 10, 4117.
(i) Shaabani, A.; Rahmati, A.; Badri, Z. Catal. Commun. 2008, 9, 13.
(j) Manske, R. Chem. Rev. 1942, 30, 113.
(k) Prajapati, S. M.; Patel, K. D.; Vekariya, R. H.; Panchal, S. N.; Patel, H. D. RSC Adv. 2014, 4, 24463.
[9] (a) Zhang, F.-L.; Hong, K.; Li, T.-J.; Park, H.; Yu, J.-Q. Science 2016, 351, 252.
(b) Wang, X.-C.; Gong, W.; Fang, L.-Z.; Zhu, R.-Y.; Li, S.; Engle, K. M.; Yu, J.-Q. Nature 2015, 519, 334.
(c) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
(d) Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007.
(e) Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236.
(f) Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2011, 45, 788.
(g) Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464.
(h) Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293.
(i) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792.
(j) Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074.
[10] Xu, Y. M.S. Thesis, Henan Normal University, Xinxiang, 2015(in Chinese). (徐亚琼, 硕士论文, 河南师范大学, 新乡, 2015.)
[11] (a) Berman, A. M.; Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 14926.
(b) Tobisu, M.; Hyodo, I.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070.
(c) Zhao, D.; Wang, W.; Yang, F.; Lan, J.; Yang, L.; Gao, G.; You, J. Angew. Chem., Int. Ed. 2009, 48, 3296.
[12] Wasa, M.; Worrell, B. T.; Yu, J. Q. Angew. Chem., Int. Ed. 2010, 49, 1275.
[13] (a) 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.
(b) Chen, Q.; du Jourdin, X. M.; Knochel, P. J. Am. Chem. Soc. 2013, 135, 4958.
[14] (a) Kwak, J.; Kim, M.; Chang, S. J. Am. Chem. Soc. 2011, 133, 3780.
(b) Boudet, N.; Lachs, J. R.; Knochel, P. Org. Lett. 2007, 9, 5525.
[15] (a) Iwai, T.; Sawamura, M. ACS Catal. 2015, 5, 5031.
(b) Stephens, D. E.; Larionov, O. V. Tetrahedron 2015, 71, 8683.
[16] (a) Liao, G.; Shi, B. Acta Chim. Sinica 2015, 73, 1283(in Chinese). (廖港, 史炳锋, 化学学报, 2015, 73, 1283.)
(b) Voskressensky, L. G.; Golantsov, N. E.; Maharramov, A. M. Synthesis 2016, 48, 615.
[17] Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797.
[18] Guo, H.; Chen, M.; Jiang, P.; Chen, J.; Pan, L.; Wang, M.; Xie, C.; Zhang, Y. Tetrahedron 2015, 71, 70.
[19] Xu, J.; Zhu, X.; Zhou, G.; Ying, B.; Ye, P.; Su, L.; Shen, C.; Zhang, P. Org. Biomol. Chem. 2016, 14, 3016.
[20] Liu, X.-X.; Wu, Z.-Y.; Luo, X.-L.; He, Y.-Q.; Zhou, X.-Q.; Fan, Y.-X.; Huang, G.-S. RSC Adv. 2016, 6, 71485.
[21] Rao, N. S.; Reddy, G. M.; Sridhar, B.; Sarma, M. H. Eur. J. Org. Chem. 2017, 2017, 438.
[22] Ding, J.; Li, W.; Ye, K.; Li, J. ChemistrySelect 2016, 1, 5874.
[23] He, X.; Xu, Y.-Z.; Kong, L.-X.; Wu, H.-H.; Ji, D.-Z.; Wang, Z.-B.; Xu, Y.-G.; Zhu, Q.-H. Org. Chem. Front. 2017, 4, 1046.
[24] Su, Q.; Wu, Q.; Wu, C.; Zhou, H.; He, M.; Li, P.; Mu, Y. Synlett 2016, 27, 868.
[25] Sahoo, H.; Ramakrishna, I.; Baidya, M. ChemistrySelect 2016, 1, 1949.
[26] Khan, B.; Kant, R.; Koley, D. Adv. Synth. Catal. 2016, 358, 2352.
[27] Wang, Y.; Wang, Y.; Jiang, K.; Zhang, Q.; Li, D. Org. Biomol. Chem. 2016, 14, 10180.
[28] Sen, C.; Sahoo, T.; Ghosh, S. C. ChemistrySelect 2017, 2, 2745.
[29] Chen, J.; Wang, T.; Liu, Y.; Wang, T.; Lin, A.; Yao, H.; Xu, J. Org. Chem. Front. 2017, 4, 622.
[30] Huang, C.-B.; Chen, L.-J.; Huang, J.; Xu, L. RSC Adv. 2014, 4, 19538.
[31] Cong, X.; Zeng, X. Org. Lett. 2014, 16, 3716.
[32] Reddy, M. D.; Fronczek, F. R.; Watkins, E. B. Org. Lett. 2016, 18, 5620.
[33] Du, C.; Li, P.-X.; Zhu, X.; Suo, J.-F.; Niu, J.-L.; Song, M.-P. Angew. Chem., Int. Ed. 2016, 55, 13571.
[34] Zhang, J.; Wang, Z.; Ren, C.; Niu, J.; Song, M. Chin. J. Org. Chem. 2017, 37, 1237(in Chinese). (张家恒, 郝新奇, 王正龙, 任常久, 牛俊龙, 宋毛平, 有机化学, 2017, 37, 1237.)
[35] Cui, M.; Liu, J.-H.; Lu, X.-Y.; Lu, X.; Zhang, Z.-Q.; Xiao, B.; Fu, Y. Tetrahedron Lett. 2017, 58, 1912.
[36] Sahoo, H.; Reddy, M. K.; Ramakrishna, I.; Baidya, M. Chem. Eur. J. 2016, 22, 1592.
[37] Wu, Z.; He, Y.; Ma, C.; Zhou, X.; Liu, X.; Li, Y.; Hu, T.; Wen, P.; Huang, G. Asian J. Org. Chem. 2016, 5, 724.
[38] Kuninobu, Y.; Nishi, M.; Kanai, M. Org. Biomol. Chem. 2016, 14, 8092.
[39] Jin, L.-K.; Lu, G.-P.; Cai, C. Org. Chem. Front. 2016, 3, 1309.
[40] Xu, J.; Qiao, L.; Ying, B.; Zhu, X.; Shen, C.; Zhang, P. Org. Chem. Front. 2017, 4, 1116.
[41] Shen, C.; Xu, J.; Ying, B.; Zhang, P. ChemCatChem 2016, 8, 3560.
[42] Chen, H.; Li, P. H.; Wang, M.; Wang, L. Org. Lett. 2016, 18, 4794.
[43] Sahoo, H.; Mandal, A.; Selvakumar, J.; Baidya, M. Eur. J. Org. Chem. 2016, 2016, 4321.
[44] Chen, J.; Wang, T.; Wang, T.; Lin, A.; Yao, H.; Xu, J. Org. Chem. Front. 2016, 4, 130.
[45] Liang, H. W.; Jiang, K.; Ding, W.; Yuan, Y.; Shuai, L.; Chen, Y. C.; Wei, Y. Chem. Commun. 2015, 51, 16928.
[46] Qiao, H.; Sun, S.; Yang, F.; Zhu, Y.; Zhu, W.; Dong, Y.; Wu, Y.; Kong, X.; Jiang, L.; Wu, Y. Org. Lett. 2015, 17, 6086.
[47] Fu, R.; Lu, T.; Chen, F.-W. Acta Phys.-Chim. Sin. 2014, 30, 628.
[48] Xu, J.; Shen, C.; Zhu, X.; Zhang, P.; Ajitha, M. J.; Huang, K. W.; An, Z.; Liu, X. Chem. Asian J. 2016, 11, 882.
[49] Li, J.-M.; Weng, J.; Lu, G.; Chan, A. S. C. Tetrahedron Lett. 2016, 57, 2121.
[50] Wei, J.; Jiang, J.; Xiao, X.; Lin, D.; Deng, Y.; Ke, Z.; Jiang, H.; Zeng, W. J. Org. Chem. 2016, 81, 946.
[51] Liang, S.; Manolikakes, G. Adv. Synth. Catal. 2016, 358, 2371.
[52] Xia, C.; Wang, K.; Xu, J.; Wei, Z.; Shen, C.; Duan, G.; Zhu, Q.; Zhang, P. RSC Adv. 2016, 6, 37173.
[53] Ji, D.; He, X.; Xu, Y.; Xu, Z.; Bian, Y.; Liu, W.; Zhu, Q.; Xu, Y. Org. Lett. 2016, 18, 4478.
[54] Wang, Y.; Wang, Y.; Guo, Z.; Zhang, Q.; Li, D. Asian J. Org. Chem. 2016, 5, 1438.
[55] Yin, Y.; Xie, J.; Huang, F.-Q.; Qi, L.-W.; Zhang, B. Adv. Synth. Catal. 2017, 359, 1037.
[56] Dou, Y.; Xie, Z.; Sun, Z.; Fang, H.; Shen, C.; Zhang, P.; Zhu, Q. ChemCatChem 2016, 8, 3570.
[57] Whiteoak, C. J.; Planas, O.; Company, A.; Ribas, X. Adv. Synth. Catal. 2016, 358, 1679.
[58] Khan, B.; Khan, A. A.; Bora, D.; Verma, D.; Koley, D. ChemistrySelect 2017, 2, 260.
[59] Zhu, X.; Qiao, L.; Ye, P.; Ying, B.; Xu, J.; Shen, C.; Zhang, P. RSC Adv. 2016, 6, 89979.
[60] He, Y.; Zhao, N.; Qiu, L.; Zhang, X.; Fan, X. Org. Lett. 2016, 18, 6054.
[61] Sadhu, P.; Alla, S. K.; Punniyamurthy, T. J. Org. Chem. 2015, 80, 8245.
[62] Xia, C.; Wang, K.; Xu, J.; Shen, C.; Sun, D.; Li, H.; Wang, G.; Zhang, P. Org. Biomol. Chem. 2017, 15, 531.
[63] Wang, H.; Niu, Y.; Zhang, G.; Ye, X.-S. Tetrahedron Lett. 2016, 57, 4544.
[64] Chen, F.-J.; Zhao, S.; Hu, F.; Chen, K.; Zhang, Q.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 4187.
[65] Wang, C.; Yang, Y.; Qin, D.; He, Z.; You, J. J. Org. Chem. 2015, 80, 8424.