Chinese Journal of Organic Chemistry >
Synthesis of Isoquinolines Derivatives from o-Alkynyl Aldehydes
Received date: 2016-04-14
Revised date: 2016-05-20
Online published: 2016-06-02
Supported by
Project supported by the National Natural Science Foundation of China (Nos.21372070, 21471052), and the Hunan Provincial Education Office Scientific Research Foundation Project (No.14k035).
The isoquinoline and dihydroisoquinoline ring systems are found as the core nucleus in a wide variety of natural products and pharmaceutical agents with good biologically activity. Isoquinoline, benzoxazine-fused isoquinlines and pyrazo-lo[5,1-a]isoquinolines are prepared from o-alkynyl aldehydes and nitrogen-containing compounds via tandem reactions catalyzed by CuI or AgNO3. The reactions have some advantages, such as mild reaction conditions, simple operation and easily available catalysts.
Li Yubo , Zhao Yunhui , Luo Mingjian , Tang Zilong , Cao Chaotun , Deng Keqin . Synthesis of Isoquinolines Derivatives from o-Alkynyl Aldehydes[J]. Chinese Journal of Organic Chemistry, 2016 , 36(10) : 2504 -2509 . DOI: 10.6023/cjoc201604031
[1] (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341. (c) Inoue, K.; Kulsum, U.; Chowdhury, S. A.; Fujisawa, S. I.; Ishihara, M.; Yokoe I.; Sakagami, H. Anticancer Res. 2005, 25, 4053. (d) Su, S.; Porco Jr., J. A. Org. Lett. 2007, 9, 4983.
[2] (a) Wada, Y.; Nishida, N.; Kurono, N.; Ohkuma, T.; Orito, K. Eur. J. Org. Chem. 2007, 4320. (b) Sun, Y.; Xun, K.; Wang Y.; Chen, X. Anti-Cancer Drugs 2009, 20, 757. (c) Wong, N. C. W.; Tucker, J. E. L.; Hansen, H. C.; Chiacchia, F. S.; McCaffrey, D. US 2008188467, 2008,[Chem. Abstr. 2008, 149, 246409].
[3] (a) Liu, S.-J.; Zhao, Q.; Chen, R.-F.; Deng, Y.; Fan, Q.-L.; Li, F.-Y.; Wang, L.-H.; Huang, C.-H.; Huang, W. Chem. Eur. J. 2006, 12, 4351. (b) Zhao, Q.; Liu, S.; Shi, M.; Wang, C.; Yu, M.; Li, L.; Li, F.; Yi, T.; Huang, C. Inorg. Chem. 2006, 45, 6152. (c) Tsuboyama, A.; Iwawaki, H.; Furugori, M.; Mukaide, T.; Kamatani, J.; Igawa, S.; Moriyama, T.; Miura, S.; Takiguchi, T.; Okada, S.; Hoshino, M.; Ueno, K. J. Am. Chem. Soc. 2003, 125, 12971.
[4] (a) Tiwari, V. K.; Pawar, G. G.; Jena, H. S.; Kapur, M. Chem. Commun. 2014, 50, 7322. (b) Liu, Y.; Zeng, R.; Pan, J.; Zou, J. Chin. J. Chem, 2014, 32, 883. (c) Shi, L.; Ji, Y.; Huang, W.; Zhou, Y. Acta Chim. Sinica 2014, 72, 820(in Chinese). (时磊, 姬悦, 黄文学, 周永贵, 化学学报, 2014, 72, 820.) (d) Ma, J.; Zhai, Y.; Zhu, L.; Zhao, Y. Chin. J. Org. Chem. 2015, 35, 2366(in Chinese). (马金龙, 翟艳光, 朱俐, 赵育, 有机化学, 2015, 35, 2366.)
[5] (a) Sotomayor, N.; Dominguez, E. J. Org. Chem. 1996, 61, 4062. (b) Ishikawa, T.; Shimooka, K.; Narioka, T.; Noguchi, S.; Saito, T.; Ishikawa, A.; Yamazaki, E.; Harayama, T.; Seki, H.; Yamaguchi, K. J. Org. Chem. 2000, 65, 9143.
[6] (a) Boudou, M.; Enders, D. J. Org. Chem. 2005, 70, 9486. (b) Walker, E. R.; Leung, S. Y.; Barrett, A. G. M. Tetrahedron Lett. 2005, 46, 6537.
[7] (a) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797. (b) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 341. (c) Youn, S. W. J. Org. Chem. 2006, 71, 2521.
[8] Maassarani, F.; Pfeffer, M.; Le Borgne, G. J. Chem. Soc., Chem. Commun. 1987, 8, 565.
[9] Wu, G.; Geib, S. J.; Rheingold, A. L.; Heck, R. F. J. Org. Chem. 1988, 53, 3238.
[10] Girling, I. R.; Widdowson, D. A. Tetrahedron Lett. 1982, 23, 4281.
[11] (a) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (b) Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 980. (c) Ramakrishna, T. V. V.; Sharp, P. R. Org. Lett. 2003, 5, 877. (d) Lim, S.-G.; Lee, J. H.; Moon, C. W.; Hong, J.-B.; Jun, C.-H. Org. Lett. 2003, 5, 2759. (e) Korivi, R. P.; Cheng, C.-H. Org. Lett. 2005, 7, 5179. (f) Wang, B.; Lu, B.; Jiang, Y.; Zhang, Y.; Ma, D. Org. Lett. 2008, 10, 2761. (g) Chiba, S.; Xu, Y.-J.; Wang, Y.-F. J. Am. Chem. Soc. 2009, 131, 12886. (h) Florentino, L.; Aznar, F.; Valdés, C. Org. Lett. 2012, 14, 2323. (i) Li, C.; An, S.; Zhu, Y.; Zhang, J.; Kang, Y.; Liu, P.; Wang, Y.; Li, J. RSC Adv. 2014, 4, 49888.
[12] (a) Chen, Z.; Yang, X.; Wu, J. Chem. Commun. 2009, 3469. (b) Chen, Z.; Ding, Q.; Yu, X.; Wu, J. Adv. Synth. Catal. 2009, 351, 1692. (c) Liu, G.; Liu, H.; Qiu, G.; Pu, S.; Wu, J. Chem. Commun. 2012, 7049.
[13] Niu, Y.-N.; Yan, Z.-Y.; Gao, G.-L.; Wang, H.-L.; Shu, X.-Z.; Ji, K.-G.; Liang, Y.-M. J. Org. Chem. 2009, 74, 2893.
[14] Hwang S.; Lee, Y.; Lee, P.; Shin, S. Tetrahedron Lett. 2009, 50, 2305.
[15] Kobayashi, M.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2007, 48, 7019.
[16] Yu, X.; Yang, Q.; Lou, H.; Peng, Y.; Wu, J. Org. Biomol. Chem. 2011, 9, 7033.
[17] (a) Zhao, Y.-H.; Li, Y.; Guo, T.; Tang, Z.; Deng, K.; Zhao, G. Synth. Commun. 2016, 46, 355. (b) Zhao, Y.-H.; Li, Y.; Guo, T.; Tang, Z.; Xie, W.; Zhao, G. Tetrahedron Lett. 2016, 57, 2257.
/
| 〈 |
|
〉 |
