基于多米诺反应合成吲哚衍生物
收稿日期: 2014-03-06
修回日期: 2014-05-04
网络出版日期: 2014-05-23
基金资助
福建省闽江学者计划（No.10BS216）、厦门南方海洋研究中心（No.13GYY003NF16）、华侨大学基本科研业务基金资助项目
Synthesis of Indole Derivatives via Domino Reactions
Received date: 2014-03-06
Revised date: 2014-05-04
Online published: 2014-05-23
Supported by
Project supported by the Minjiang Scholar Program (No. 10BS216), the Xiamen Southern Oceanographic Center (No. 13GYY003NF16), and the Fundamental Research Funds of Huaqiao University
冯亚栋 , 张红 , 程国林 , 崔秀灵 . 基于多米诺反应合成吲哚衍生物[J]. 有机化学, 2014 , 34(8) : 1499 -1508 . DOI: 10.6023/cjoc201403015
Domino reactions have received great attentions of organic chemist as an efficient protocol to synthesize indole derivatives. In this process, it is not required isolating or purifying the intermediates, changing the reaction condition and adding reagents. Transition metal-catalyzed domino reactions to synthesize indole derivatives have already been widely studied and become a powerful tool. In this paper, the progress of recent domino reactions applied to construct indole and its derivatives is reviewed, focusing on the transition metal-catalyzed domino reactions, and detailed analysis on the versatility and applications.
Key words： domino reactions; metal catalysis; indole derivatives; synthesis
[1] Sundberg, R. J. Indoles, Academic Press, London, 1996, pp. 12～15.
[2] Joule, J. A.; Thomas, E. J. Sci. Synth. 2001, 361.
[3] Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
[4] Fischer, E.; Jourdan, F. Ber 1883, 16, 2241.
[5] Mori, M.; Chiba, K.; Ban, Y. Tetrahedron Lett. 1977, 1, 1037.
[6] Hemetsberger, H.; Knittel, D.; Weidmann, H. Monatsh. Chem. 1970, 101, 161.
[7] Aold, K.; Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 3068.
[8] Sundberg, R. J.; Lin, L. S.; Blackburn, D. E. J. Heterocycl. Chem. 1969, 6, 441.
[9] Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253.
[10] Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
[11] Li, S.; Han, J.; L, A. Acta Chim. Sinica 2013, 71, 295 (in Chinese).
(李森, 韩静, 李昂, 化学学报, 2013, 71, 295.)
[12] (a) Zuo, Z. Z.; Xie, W. Q.; Ma, D. W. J. Am. Chem. Soc. 2010, 132, 13226.
(b) Zuo, Z. W.; Ma, D. W. Angew. Chem., Int. Ed. 2011, 50, 12008.
(c) Zi, W. W.; Xie, W. Q.; Ma, D. W. J. Am. Chem. Soc. 2012, 134, 9126.
[13] Zhang, D.; Qin, Y. Acta Chim. Sinica 2013, 71, 147 (in Chinese).
(张丹, 秦勇, 化学学报, 2013, 71, 147.)
[14] Qiu, H.; Zhang, D.; Liu, S. Y.; Qiu, L.; Zhou, J.; Qian, Y.; Zhai, C. W.; Hu, W. H. Acta Chim. Sinica 2012, 70, 2484 (in Chinese).
(邱晃, 张丹, 刘顺英, 邱林, 周俊, 钱宇, 翟昌伟, 胡文浩, 化学学报, 2012, 70, 2484.)
[15] Tietze, L. F. Chem. Rev. 1996, 96(1), 115.
[16] Tietze, L. F.; Brasche, G.; Gericke, K. M. Dmino Reactions in Organic Synthesis, Weinheim, Wiley-VCH, 2006, pp. 25～30.
[17] Wender, P. A.; Miller, B. L. Nature 2009, 460(7252), 197.
[18] Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 16, 2671.
[19] Barluenga, J.; Jimenez-Aquino, A.; Valdes, C.; Aznar, F. Angew. Chem., Int. Ed. 2007, 46, 1529.
[20] Barluenga, J.; Jimenez-Aquino, A.; Aznar, F.; Valdes, C. J. Am. Chem. Soc. 2009, 131, 4031.
[21] Jensen, T.; Pedersen, H., Bang-Andersen, B.; Madsen, R.; Jørgensen, M. Angew. Chem., Int. Ed. 2008, 47, 888.
[22] Wurtz, S.; Rakshit, S.; Neumann, J.; Droge, T.; Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 7230.
[23] Shi, Z. Z.; Zhang, C.; Li, S.; Pan, D. L.; Ding, S. T.; Cui, Y. X.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 4572.
[24] Romagnoli, R.; Baraldi, P. G.; Sarkar, T.; Carrion, M. D.; Cara, C. L.; Preti, D.; Tabrizi, M. A.; Tolomeo, M.; Grimaudo, S.; Zonta, N.; Balzarini, J.; Brancale, A.; Hsieh, H.-P.; Hamel, E. J. Med. Chem. 2008, 51, 1464.
[25] Mahboobi, S.; Pongratz, H.; Hufsky, H.; Hockemeyer, J.; Frieser, M.; Lyssenko, A.; Paper, D. H.; Burgermeister, J.; Bohmer, F.-D.; Fiebig, H.-H.; Burger, A. M.; Baasner, S.; Beckers, T. J. Med. Chem. 2001, 44, 4535.
[26] Arthuis, M.; Pontikis, R.; Florent, C. Org. Lett. 2009, 11, 4608.
[27] Mao, H.; Wan, J. P.; Pan, Y. J.; Sun, C. R. Tetrahedron Lett. 2010, 51, 1844.
[28] Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
[29] Catellani, M.; Motti, E.; Della, C. N. Acc. Chem. Res. 2008, 41, 1512.
[30] Candito, D. A.; Lautens, M. Org. Lett. 2010, 12, 3312.
[31] Faccini, F.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2004, 126, 78.
[32] Hassner, A.; Bunnell, C. A.; Haltiwanger, K. J. J. Org. Chem. 1978, 43, 57.
[33] Shen, J. H.; Cheng, G. L.; Cui, X. L. Prog. Chem. 2012, 24, 1324 (in Chinese).
(沈金海, 程国林, 崔秀灵, 化学进展, 2012, 24, 1324.)
[34] Wang, Y.; Wang, H.; Peng, J.; Zhu, Q. Org. Lett. 2011, 13, 4604.
[35] Nanjo, T.; Tsukano, C.; Takemoto, Y. Org. Lett. 2012, 14, 4270.
[36] Piou, T.; Neuville, L.; Zhu, J. P. Tetrahedron 2013, 69, 4415.
[37] Fernandez, L. S.; Buchanan, M. S.; Carroll, A. R.; Feng, Y. J.; Quinn, R. J.; Avery, V. M. Org. Lett. 2009, 11, 329.
[38] Yokoyama, Y.; Matsumoto, T.; Murakami, Y. J. Org. Chem. 1995, 60, 1486.
[39] Tan, B.; Torres, G. H.; Barbas, C. F. J. Am. Chem. Soc. 2011, 133, 12354.
[40] Love, B. E.; Raje, P. S. Synlett 1995, 1061.
[41] Zhang, Y. H.; Liu, S.; Yu, W. W.; Hu, M.; Zhang, G. L.; Yu, Y. P. Tetrahedron 2013, 69, 2070.
[42] Xu, C.; Murugan, V. K.; Pullarkat, S. A. Org. Biomol. Chem. 2012, 10, 3875.
[43] Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 6(49), 4387.
[44] Bandini, M.; Melloni. A.; Ronchi, A. U. Angew. Chem., Int. Ed. 2004, 43, 550.
[45] Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054.
[46] Li, J. H.; Tang, B. X.; Tao, L. M.; Xie, Y. X.; Liang, Y.; Zhang, M. B. J. Org. Chem. 2006, 71, 7488.
[47] Altman, R. A.; Buchwald, S. L. Org. Lett. 2006, 8, 2779.
[48] Chen, Y.; Xie, X. A.; Ma, D. W. J. Org. Chem. 2007, 72, 9329.
[49] Ali, M. A.; Punniyamurthy, T. Synlett 2011, 623.
[50] Xia, Z. M.; Wang, K.; Zheng, J. N.; Ma, Z. Y.; Jiang, Z. J.; Wang, X. X.; Lv, X. Org. Biomol. Chem. 2012, 10, 1602.
[51] Ma, S.; Cai, Q. Acc. Chem. Res. 2008, 41, 1451.
[52] Oda, Y.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2012, 14, 664.
[53] Salzner, U.; Lagowski, J. B.; Pickup, P. G.; Poirier, R. A. Synth. Met. 1998, 96, 177.
[54] Park, J.; Park, E.; Kim, A.; Park, S. A.; Lee, Y.; Chi, K. W.; Jung, Y. H.; Kim, I. S. J. Org. Chem. 2011, 76, 2214.
[55] Ponpandian, T.; Muthusubramanian, S. Tetrahedron Lett. 2012, 53, 4248.
[56] Ambrogio, I.; Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2007, 1775.
[57] Praveen, C.; Karthikeyan, K.; Perumal, P. T. Tetrahedron 2009, 65, 9244.
[58] Chang, H. O.; Karmakar, S.; Park, H.; Ahn, Y.; Kim, J. W. J. Am. Chem. Soc. 2010, 132, 1792.
[59] Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474.
[60] Boyer, A.; Isono, N.; Lackner, S.; Lautens, M. Tetrahedron 2010, 66, 6468.
[61] Schonhaber, J.; Frank, W.; Muller, T. J. J. Org. Lett. 2010, 12, 4122.
[62] Reddy, B. V. S.; Swain, M.; Reddy, S. M.; Yadav, J. S.; Sridhar, B. J. Org. Chem. 2012, 77, 11355.
[63] Cui, S. L.; Wang, J.; Wang, Y. G. J. Am. Chem. Soc. 2008, 130, 13526.
[64] Jiang, B.; Li, Q. Y.; Tu, S. J.; Li, G. G. Org. Lett. 2012, 14, 5210.
/
| 〈 |
|
〉 |
