Chinese Journal of Organic Chemistry >
Research Progress in the Synthesis of 3-Indolecarboxylates
Received date: 2017-12-06
Revised date: 2018-01-06
Online published: 2018-01-18
Supported by
Project supported by the National Natural Science Foundation of China (No. 21302039) and the Natural Science Foundation of Hebei Province (No. B2016208124).
Indole derivatives have been considered as “privileged scaffolds” in drug discovery since they are capable of binding many receptors with high affinity. 3-Indolecarboxylates are widespread structure motifs in many natural products and drug molecules, such as arbidol, tropisetron, PD 0298029, and grandilodine A, etc. Consequently, synthetic studies toward 3-indolecarboxylates have been reported in recent years. Elegant cyclization strategies have been developed via transition-metal catalyzed or transition-metal-free reactions, and direct functionalization at C-3 position for synthesis of ester functional groups was also extremely attractive. Based on our studies toward synthesis of 3-indolecarboxylates, the recent developments of synthesis of 3-indolecarboxylates by different synthetic methods in view of the types of substrates are reviewed.
Xue Hong , Dong Yu , Feng Lei , Li Haibo , Li Jin , Zhang Zhiwei . Research Progress in the Synthesis of 3-Indolecarboxylates[J]. Chinese Journal of Organic Chemistry, 2018 , 38(5) : 1029 -1034 . DOI: 10.6023/cjoc201712010
[1] Somei, M.; Yamada, F. Nat. Prod. Rep. 2003, 34, 761.
[2] Zhao, C.; Zhao, Y.; Chai, H.; Gong, P. Bioorg. Med. Chem. 2006, 14, 2552.
[3] Boriskin, Y. S.; Leneva, I. A.; Pecheur, E. I.; Polyak, S. J. Curr. Med. Chem. 2008, 15, 997.
[4] Sheridan, R. P.; Korzekwa, K. R.; Torres, R. A.; Walker, M. J. J. Med. Chem. 2007, 50, 3173.
[5] Augelli-Szafran, C. E.; Jaen, J. C.; Morelang, D. W.; Nelson, C. B.; Penvose-Yi, J. R.; Schwarz, R. D. Bioorg. Med. Chem. Lett. 1998, 8, 1991.
[6] Schultz, E. E.; Pujanauski, B. G.; Sarpong, R. Org. Lett. 2012, 14, 648.
[7] Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195.
[8] Wurtz, S.; Rakshit, S.; Neumann, J. J.; Droge, T.; Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 7230.
[9] Sole, D.; Serrano, O. J. Org. Chem. 2008, 73, 2476.
[10] Söderberg, B. C. G.; Banini, S. R.; Turner, M. R.; Minter, A. R.; Arrington, S. K. Synthesis 2008, 903.
[11] Shen, D.; Han, J.; Chen, J.; Deng, H.; Shao, M.; Zhang, H.; Cao, W. Org. Lett. 2015, 17, 3283.
[12] Okuro, K.; Gurnham, J.; Alper, H. J. Org. Chem. 2011, 76, 4715.
[13] Jiang, H.; Gao, S.; Xu, J.; Wu, X.; Lin, A.; Yao, H. Adv. Synth. Catal. 2016, 358, 188.
[14] Yu, K.; Liang, Y.; Li, B.; Wang, B. Adv. Synth. Catal. 2016, 358, 661.
[15] Watanabe, T.; Mutoh, Y.; Saito, S. J. Am. Chem. Soc. 2017, 139, 7749.
[16] Li, H.; Zhao, Y.; Ma, L.; Ma, M.; Jiang, J.; Wan, X. Chem. Commun. 2017, 53, 5993.
[17] Zhang, X.-X.; Sun, X.-P.; Zhang, H.-F.; Cui, X.-L.; Ma, M.-T. Chin. J. Org. Chem. 2015, 35, 1469(in Chinese). (张小祥, 孙小萍, 张海飞, 崔杏丽, 马猛涛, 有机化学, 2015, 35, 1469.)
[18] Lee, K.-Y.; Lee, H.-S.; Kim, J.-N. Bull. Korean Chem. Soc. 2007, 28, 333.
[19] Levesque, P.; Fournier, P. A. J. Org. Chem. 2010, 75, 7033.
[20] Mahavir, P.; Vecchia, L. L.; Kapa, P.; Oljan, R. Synth. Commun. 1995, 25, 95.
[21] Islam, M. S.; Brennan, C.; Wang, Q.; Hossain, M.-M. J. Org. Chem. 2006, 71, 4675.
[22] (a) Natarajan, R.; Rappai, J.; Unnikrishnan, P.; Radhamani, S.; Prathapan, S. Synlett 2015, 26, 2467.
(b) Tang, S.; Gao, X.; Lei, A. Chem. Commum. 2017, 53, 3354.
[23] Peterson, P.; Iii, J. W.; Niemann, C. J. Org. Chem. 1958, 23, 303.
[24] Lang, R.; Wu, J.; Shi, L.; Xia, C.; Li, F. Chem. Commun. 2011, 47, 12553.
[25] Lang, R.; Shi, L.; Li, D.; Xia, C.; Li, F. Org. Lett. 2012, 14, 4130.
[26] Zhang, H.; Liu, D.; Chen, C.; Liu, C.; Lei, A. Chem.-Eur. J. 2011, 17, 9581.
[27] Yang, Q.-Q.; Marchini, M.; Xiao, W.-J.; Ceroni, P.; Bandini, M. Chem.-Eur. J. 2015, 21, 18052.
[28] Nemoto, K.; Tanaka, S.; Konno, M.; Onozawa, S. Tetrahedron 2016, 72, 734.
[29] Zhang, Z.-W.; Xue, H.; Li, H.; Kang, H.; Feng, J.; Lin, A. Org. Lett. 2016, 18, 3918.
/
| 〈 |
|
〉 |