Progress in the Research of Copper Promoted C—H Functionalizations for the Synthesis of Fused Heterocycles Bearing Bridgehead Nitrogen

doi:10.6023/cjoc201504013

Abstract

The copper-catalyzed C—H activation, selective functionalization and the development of cyclization strategy for the synthesis of novel fused-heterocyclic (heterocycles with ring-junction nitrogen or bridgehead nitrogen) compounds are discussed. This class of novel bridgehead nitrogen heterocycles includes indolizine, pyrazolopyridine, benzimidazole and other polyheterocyclic compounds. The series including modern amination, oxidative coupling and C_sp²—H, C_sp—H, C_sp³—H and N—H activation catalyzed by Cu(I) or Cu(II) salts makes this green synthesis a superior and practical method providing entry into complex heterocycles. Some reaction mechanisms have also been summarized.

Key words: copper-catalyzed, bridgehead nitrogen fused-heterocycles, oxidative coupling, C—H activation, N—H activation, cyclization, annulation

Cite this article

Zhang Yingjun, Nie Biao, Zhang Ji. Progress in the Research of Copper Promoted C—H Functionalizations for the Synthesis of Fused Heterocycles Bearing Bridgehead Nitrogen[J]. Chin. J. Org. Chem., 2015, 35(10): 2067-2085.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Li, J. J. Laughing Gas, Viagra, and Lipitor, 198 Madison Avenue, New York, USA, 2006, p. 103.
[2] Li, J. J.; Johnson, D. S., Sliskovic, D. R.; Roth, B. D. Contemporary Drug Synthesis, Hoboken, New Jersey, USA, 2004, p. 189.
[3] Edmondson, S. D.; Xu, F.; Armstrong III, J. D. In Mondern Drug Synthesis, Eds.: Li, J. J.; Johnson, D. S., Hoboken, New Jersey, USA, 2010, p. 125.
[4] (a) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. (b) Zheng, H. Medicinal Chemistry, 6th ed., People's Medical Publishing House, Beijing, 2007, p. 13 (in Chinese).(郑虎, 药物化学, 第6版, 人民卫生出版社, 北京, 2007, p. 13.)
[5] Kettle, J. G.; Brown, S.; Crafter, C.; Davies, B. R.; Dudley, P.; Fairley, G.; Faulder, P.; Fillery, S.; Greenwood, H.; Hawkins, J.; James, M.; Johnson, K.; Lane, C. D.; Pass, M.; Pink, J. H.; Plant, H.; Cosulich, S. C. J. Med. Chem. 2012, 55, 1261.
[6] Jorg, M.; May, L. T.; Mak, F. S.; Lee, K. C. K.; Miller, N. D.; Scammells, P. J.; Capuano, B. J. Med. Chem. 2015, 58, 718.
[7] Peterson, E. A.; Teffera, Y.; Albrecht, B. K.; Bauer, D.; Bellon, S. F.; Boezio, A.; Boezio, C.; Broome, M. A.; Choquette, D.; Copeland, K. W.; Dussault, I.; Lewis, R.; Lin, M. H.; Lohman, J.; Liu, J.; Potashman, M.; Rex, K.; Shimanovich, R.; Whittington, D. A.; Vaida K. R.; Harmange, J. C. J. Med. Chem. 2015, 58, 2417.
[8] Gudmundsson, K. S.; Williams, J. D.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 2003, 46, 1449.
[9] Das, S.; Fröhlich, R.; Pramanik, A. Org. Lett. 2006, 8, 4263.
[10] Guo, X. X.; Gu, D. W.; Wu, Z. X.; Zhang, W. B. Chem. Rev. 2015, 115, 1622.
[11] Krause, N. Modern Organocopper Chemistry, Wiley-VCH, Weinheim, 2002.
[12] (a) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (b) Allen, S. E.; Walvoord, R. R.; Padilla-Salinas, R.; Kozlowski, M. C. Chem. Rev. 2013, 113, 6234.
[13] Ma, D. W.; Zhang, Y. D.; Yao, J. C.; Wu, S. H.; Tao, F. G. J. Am. Chem. Soc. 1998, 120, 12459
[14] Cheng, Y. J.; Sun, L. P. Chin. J. Org. Chem. 2013, 33, 877 (in Chinese). (成宜娟, 孙丽萍, 有机化学, 2013, 33, 877.)
[15] Li, Z. K.; Wu, Z. Q.; Deng, H.; Zhou, X. G. Chin. J. Org. Chem. 2013, 33, 760 (in Chinese). (李正凯, 吴之清, 邓杭, 周向葛, 有机化学, 2013, 33, 760.)
[16] Yu, H. Z.; Su, S. Q.; Zhang, C.; Dang, Z. M. Chin. J. Org. Chem. 2013, 33, 1628 (in Chinese). (于海珠, 苏圣钦, 张弛, 党智敏, 有机化学, 2013, 33, 1628.)
[17] Liao, Q.; Xi, C. J. Chin. J. Org. Chem. 2012, 32, 986 (in Chinese). (廖骞, 席婵娟, 有机化学, 2012, 32, 986.)
[18] Liu, Q.; Tian, B.; Tian, P.; Tong, X. F.; Lin, G, Q. Chin. J. Org. Chem. 2015, 35, 1 (in Chinese). (刘强, 田兵, 田平, 童晓峰, 林国强, 有机化学, 2015, 35, 1.)
[19] Deng, W.; Liu, L.; Guo, Q. X. Chin. J. Org. Chem. 2004, 24, 150 (in Chinese).(邓维, 刘磊, 郭庆祥, 有机化学, 2004, 24, 150.)
[20] (a) Wang, Y. F.; Zeng, J. H.; Cui, X. R. Chin. J. Org. Chem. 2010, 30, 181 (in Chinese). (王晔峰, 曾京辉, 崔晓瑞, 有机化学, 2010, 30, 181.)
[21] Xu, H. J.; Man, Q. S.; Lin, Y. C.; Li, Y. Y.; Feng, Y. J. Chin. J. Org. Chem. 2010, 30, 9 (in Chinese).(许华建, 蔄秋石, 林义成, 李源源, 冯乙巳, 有机化学, 2010, 30, 9.)
[22] Liu, W.; Bi, Y. L. Chin. J. Org. Chem. 2012, 32, 1041 (in Chinese). (刘伟, 毕艳兰, 有机化学, 2012, 32, 1041.)
[23] Wang, H. G.; Wang, Y.; Peng, C. L.; Zhang, J. C.; Zhu, Q. J. Am. Chem. Soc. 2010, 132, 13217.
[24] Wang, H. G.; Wang, Y.; Liang, D. D.; Liu, L. Y.; Zhang, J. C.; Zhu, Q. Angew. Chem., Int. Ed. 2011, 50, 5678.
[25] Barluenga, J.; Lonzi, G.; Riesgo, L.; Lopez, L. A.; Tomas, M. J. Am. Chem. Soc. 2010, 132, 13200.
[26] Kiruthika, S. E.; Nandakumar, A.; Perumal, P. T. Org. Lett. 2014, 16, 4424.
[27] Sun, H.; Wang, C. M.; Yang, Y. F.; Chen, P.; Wu, Y. D.; Zhang, X. H.; Huang, Y. J. Org. Chem. 2014, 79, 11863.
[28] Bagdi, A. K.; Rahman, M.; Santra, S.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2013, 355, 1741.
[29] Masters, K. S.; Rauws, T. R. M.; Yadav, A. K.; Herrebout, W. A.; Van der Veken, B.; Maes, B. U. W. Chem. Eur. J. 2011, 17, 6315.
[30] Ohta, Y.; Kubota, Y.; Watabe, T.; Chiba, H.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2009, 74, 6299.
[31] Chernyak, N.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2743.
[32] Li, S. Y.; Wu, J. Org. Lett. 2011, 13, 712.
[33] Lu, J. Y.; Jin, Y. B.; Liu, H. X.; Jiang, Y. Y.; Fu, H. Org. Lett. 2011, 13, 3694.
[34] Liao, Q.; Zhang, L. Y.; Li, S. T.; Xi, C. J. Org. Lett. 2011, 13, 228.
[35] Sang, P.; Xie, Y. J.; Zou, J. W.; Zhang, Y. H. Org. Lett. 2012, 14, 3894.
[36] Sang, P.; Xie, Y. J.; Zou, J. W.; Zhang, Y. H. Adv. Synth. Catal. 2012, 354, 1873.
[37] Zhang, Y. F.; Chen, Z. K.; Wu, W. L.; Zhang, Y. H.; Su, W. P. J. Org. Chem. 2013, 78, 12494.
[38] Ding, S. T.; Yan, Y. P.; Jiao, N. Chem. Commun. 2013, 49, 4250.
[39] Wang, C.; Zhang, L. P.; Ren, A. N.; Lu, P.; Wang, Y. G. Org. Lett. 2013, 15, 2982.
[40] Huang, H. W.; Ji, X. C.; Tang, X. D.; Zhang, M.; Li, X. W.; Jiang, H. F. Org. Lett. 2013, 15, 6254.
[41] Yu, J. P.; Jin, Y. H.; Zhang, H.; Yang, X. B.; Fu, H. Chem. Eur. J. 2013, 19, 16804.
[42] Liu, Q.; Yang, H. J.; Jiang, Y. Y.; Zhao, Y. F.; Fu, H. RSC. Adv. 2013, 3, 15636.
[43] Li, M. Y.; Xie, Y.; Ye, Y.; Zou, Y.; Jiang, H. F.; Zeng, W. Org. Lett. 2014, 16, 6232.
[44] Tian, H.; Qiao, H. W.; Zhu, C. J.; Fu, H. RSC. Adv. 2014, 4, 2694.
[45] Ueda, S.; Nagasawa, H. J. Am. Chem. Soc. 2009, 131, 15080.
[46] Wang, X. Q.; Jin, Y. H.; Zhao, Y. F.; Zhu, L.; Fu, H. Org. Lett. 2012, 14, 452.
[47] Chen, L. J.; Li, C.; Bi, X.; Liu, H. X.; Qiao, R. Z. Adv. Synth. Catal. 2012, 354, 1773.
[48] Qian, W. Y.; Wang, H.; Allen, J. Angew. Chem., Int. Ed. 2013, 52, 10992.
[49] Wang, M.; Jin, Y. H.; Yang, H. J.; Fu, H.; Hu, L. M. RSC. Adv. 2013, 3, 8211.
[50] Chen, D. B.; Chen, Q. F.; Liu, M. C.; Dai, S. Q.; Huang, L.; Yang, J. G.; Bao, W. L. Tetrahedron. 2013, 69, 6461.
[51] Bartels, B.; Bolas, C. G.; Cueni, P.; Fantasia, S.; Gaeng, N.; Trita, A. S. J. Org. Chem. 2015, 80, 1249.
[52] Kumar, A.; Kumar, M.; Maurya, S.; Khanna, R. S. J. Org. Chem. 2014, 79, 6905.
[53] Yuan, G. D.; Liu, H. Q.; Gao, J. L.; Yang, K. J.; Niu, Q. S.; Mao, H.; Wang, X. X.; Lv, X. J. Org. Chem. 2014, 79, 1749.
[54] Pradere, U.; Garnier-Amblard, E. C.; Coats, S. J.; Amblard, F.; Schinazi, R. F. Chem. Rev. 2014, 114, 9154
[55] D'hooghe, M.; Mollet, K.; De Vreese, R.; Jonckers, T. H. M.; Dams, G.; De Kimpe, N. J. Med. Chem. 2012, 55, 5637.
[56] Sofia, M. J.; Chang, W. S.; Furman, P. A.; Mosley, R. T.; Ross, B. S. J. Med. Chem. 2012, 55, 2481.
[57] (a) Wu, C. H.; Wang, C. J.; Chang, C. P.; Cheng, Y. C.; Song, J. S.; Jan, J. J.; Chou, M. C.; Ke, Y. Y.; Ma, J.; Wong, Y. C.; Hsieh, T. C.; Tien, Y. C.; Gullen, E. A.; Lo, C. F.; Cheng, C. Y.; Liu, Y. W.; Sadani, A. A.; Tsai, C. H.; Hsieh, H. P.; Tsou, L. K.; Shia, K. S. J. Med. Chem. 2015, 58, 1452.(b) Tintori, C.; Fallacara, A. L.; Radi, M.; Zamperini, C.; Dreassi, E.; Crespan, E.; Maga, G.; Schenone, S.; Musumeci, F.; Brullo, C.; Richters, A.; Gasparrini, F.; Angelucci, A.; Festuccia, C.; Delle Monache, S.; Rauh, D.; Botta, M. J. Med. Chem. 2015, 58, 347
[58] (a) Jacobson, K. A.; Jarvis, M. F.; Williams, M. J. Med. Chem. 2002, 45, 4057.(b) Ruiz, M. D.; Lim, Y. H.; Zheng, J. Y. J. Med. Chem. 2014, 57, 3623.
[59] Qu, G. R.; Liang, L.; Niu, H. Y.; Rao, W. H.; Guo, H. M.; Fossey, J. S. Org. Lett. 2012, 14, 4494.
[60] Li, R. L.; Liang, L.; Xie, M. S.; Qu, G. R.; Niu, H. Y.; Guo, H. M. J. Org. Chem. 2014, 79, 3665.

铜促C—H官能团化合成桥头氮稠杂环化合物的研究进展