SIOC English
有机化学
高级检索

有机化学 >

2012 , Vol. 32 >Issue 07: 1217 - 1231

DOI: https://doi.org/10.6023/cjoc1109031

综述与进展

咔唑及其衍生物合成方法研究进展

  • 房旭彬 ,
  • 房雷 ,
  • 苟少华
展开
  • a 东南大学药物研究中心 南京 211189;
    b 江苏省生物药物高技术研究重点实验室 南京 211189

收稿日期: 2011-09-03

  修回日期: 2012-01-10

  网络出版日期: 2012-02-08

基金资助

国家自然科学基金(No. 81001361)和教育部博士点基金青年教师(Nos. 20100092120046)资助项目.

收起

Progresses in Synthetic Methods of Carbazole and Its Derivatives

  • Fang Xubin ,
  • Fang Lei ,
  • Gou Shaohua
Expand
  • a Pharmaceutical Research Center, Southeast University, Nanjing 211189;
    b Jiangsu Province Hi-Tech Laboratory for Bio-medical Research, Southeast University, Nanjing 211189

Received date: 2011-09-03

  Revised date: 2012-01-10

  Online published: 2012-02-08

Supported by

Project supported by the National Natural Science Foundation of China (No. 81001361) and the Ph.D. Programs Foundation of Ministry of Education of China (No. 20100092120046).

Fold

摘要

咔唑及其衍生物是一类重要的含氮芳杂环化合物, 具有许多独特的理化性质及生物活性, 分析、归纳、总结了近5 年来发表的文献, 选取具有代表性的实例, 并按照中间体的不同将合成方法分为四类, 分别讨论了咔唑及其衍生物合成方法的进展情况, 对咔唑及其衍生物成环的新方法给予重点关注.

关键词： 咔唑; 衍生物; 合成方法; 研究进展

本文引用格式

房旭彬 , 房雷 , 苟少华 . 咔唑及其衍生物合成方法研究进展[J]. 有机化学, 2012 , 32(07) : 1217 -1231 . DOI: 10.6023/cjoc1109031

Abstract

Carbazole and its derivatives are a class of important nitrogen-containing heterocyclic compounds possessing various unique properties and biological activity. Herein the current progress of their synthetic strategies reported in the past 5 years is reviewed. The representative examples, which have been divided into four categories according to the usage of different key intermediates, are selected and discussed in detail. Special emphasis is put on the newly developed cyclization reactions which may be useful for the construction of the tricyclic backbone of carbazoles.

Key words： carbazole; derivatives; synthetic methods; progress

参考文献

[1] (a) Graebe, C.; Ullmann, F. Ann. 1896, 291, 16. (b) Drechsel, E. J. Prakt. Chem. 1858, 38, 69.
[2] Preston, R. W. G.; Tucker, S. H.; Cameron, J. M. L. J. Chem. Soc. 1942, 500.
[3] (a) Bucherer, H. T. J. Prakt. Chem. 1904, 69, 49. (b) Borsche, W.; Feise, M. Ber. Dtsch. Chem. Ges. 1904, 20, 378.
[4] Yu, M.-J.; Chen, Z.-J; Lu, D.-D. Dyestuff Ind. 1998, 35, 21 (in Chinese). (俞马金, 陈中峻, 陆大东, 染料工业, 1998, 35, 21.)
[5] Chen, M.-W.; Gan, L.-Z. Organic Heterocyclic Compounds, Higher Education Press, Beijing, 1990, p. 56 (in Chinese). (陈敏为; 甘礼骓, 有机杂环化合物, 高等教育出版社, 北京, 1990, p. 56.)
[6] Sanz, R.; Escribano, J.; Pedrosa, M. R.; Aguado, R.; Arnaiz, F. J. Adv. Synth. Catal. 2007, 349, 713.  
[7] Naffziger, M. R.; Ashburn, B. O.; Perkins, J. R.; Carter, R. G. J. Org. Chem. 2007, 72, 9857.  
[8] Creencia, E. C.; Kosaka, M.; Muramatsu, T.; Kobayashi, M.; Iizuka, T.; Horaguchi, T. J. Heterocycl. Chem. 2009, 46, 1309.  
[9] Pudlo, M.; Csanyi, D.; Moreau, F.; Hajos, G.; Riedl, Z.; Sapi, J. Tetrahedron 2007, 63, 10320.  
[10] Stokes, B. J.; Jovanovic, B.; Dong, H. J.; Richert, K. J.; Riell, R. D.; Driver, T. G. J. Org. Chem. 2009, 74, 3225.  
[11] Shou, W. G.; Li, J. A.; Guo, T. X.; Lin, Z. Y.; Jia, G. C. Organometallics 2009, 28, 6847.  
[12] Jean, D. J. S.; Poon, S. F.; Schwarzbach, J. L. Org. Lett. 2007, 9, 4893.  
[13] Jordan-Hore, J. A.; Johansson, C. C. C.; Gulias, M.; Beck, E. M.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 16184.  
[14] Tsang, W. C. P.; Munday, R. H.; Brasche, G.; Zheng, N.; Buchwald, S. L. J. Org. Chem. 2008, 73, 7603.  
[15] Li, B. H.; Tian, S. L.; Fang, Z.; Shi, Z. H. Angew. Chem. Int. Ed. 2008, 47, 1115.  
[16] Kajiyama, D.; Inoue, K.; Ishikawa, Y.; Nishiyama, S. Tetrahedron 2010, 66, 9779.  
[17] Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996.  
[18] Ueno, A.; Kitawaki, T.; Chida, N. Org. Lett. 2008, 10, 1999.  
[19] Li, E. D.; Xu, X. B.; Li, H. F.; Zhang, H. M.; Xu, X. L.; Yuan, X. Y.; Li, Y. Z. Tetrahedron 2009, 65, 8961.  
[20] Kawaguchi, K.; Nakano, K.; Nozaki, K. Org. Lett. 2008, 10 (6), 1199.
[21] Watanabe, T.; Ueda, S.; Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. Chem. Commun. 2007, 43, 4516.
[22] Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2009, 74, 4720.  
[23] Liegault, B.; Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K. J. Org. Chem. 2008, 73, 5022.  
[24] Sridharan, V.; Martin, M. A.; Menéndez, J. C. Eur. J. Org. Chem. 2009, 27, 4614.
[25] Tobisu, M.; Kita, Y.; Ano, Y.; Chatani, N. J. Am. Chem. Soc. 2008, 130, 15982.  
[26] Bedford, R. B.; Butts, C. P.; Haddow, M. F.; Osborne, R.; Sankey, R. F. Chem. Commun. 2009, 32, 4832.
[27] Shimizu, M.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 3478.  
[28] Buden, M. E.; Vaillard, V. A.; Martin, S. E.; Rossi, R. A. J. Org. Chem. 2009, 74, 4490.  
[29] Tsvelikhovsky, D.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14048.  
[30] Abbiati, G.; Canevari, V.; Facoetti, D.; Rossi, E. Eur. J. Org. Chem. 2007, 2007, 517.
[31] Gioia, C.; Hauville, A.; Bernardi, L.; Fini, F.; Ricci, A. Angew. Chem. Int. Ed. 2008, 47, 9236.  
[32] Tao, M.; Park, C. H.; Josef, K.; Hudkins, R. L. J. Heterocycl. Chem. 2009, 46, 1185.  
[33] Martinez-Esperon, A. F.; Rodriguez, D.; Castedo, L.; Sáa, C. Tetrahedron 2008, 64, 3674.  
[34] Alayrac, C.; Schollmeyer, D.; Witulski, B. Chem. Commun. 2009, 1464.
[35] Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; Nagase, Y.; Miyamura, T.; Shirakawa, E. J. Am. Chem. Soc. 2008, 130, 15823.  
[36] Bourderioux, A.; Kassis, P.; Merour, J. Y.; Routier, S. Tetrahedron 2008, 64, 11012.  
[37] Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 2337.  
[38] Yamashita, M.; Horiguchi, H.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7481.  
[39] Wang, C. L.; Zhang, W.; Lu, S. C.; Wu, J. F.; Shi, Z. J. Chem. Commun. 2008, 41, 5176.
[40] Tiano, M.; Belmont, P. J. Org. Chem. 2008, 73, 4101.  
[41] acoetti, D.; Abbiati, G.; Rossi, E. Eur. J. Org. Chem. 2009, 17, 2872.
[42] adav, A. K.; Peruncheralathan, S.; Ila, H.; Junjappa, H. J. Org. Chem. 2007, 72, 1388.  
[43] Hong, X.; France, S.; Padwa, A. Tetrahedron, 2007, 63, 5962.  
[44] Mohanakrishnan, A. K.; Dhayalan, V.; Clement, J. A.; Balamurugan, R.; Sureshbabu, R.; Kumar, N. S. Tetrahedron Lett. 2008, 49, 5850.  
[45] Dhayalan, V.; Clement, J. A.; Jagan, R.; Mohanakrishnan, A. K. Eur. J. Org. Chem. 2009, 4, 531.
[46] Sureshbabu, R.; Balamurugan, R.; Mohanakrishnan, A. K. Tetrahedron 2009, 65, 3582.  
[47] Kong, W. Q.; Fu, C. L.; Ma, S. M. Chem. Commun. 2009, 30, 4572.
[48] Ramesh, N.; Rajeshwaran, G. G.; Mohanakrishnan, A. K. Tetrahedron 2009, 65, 3592.  
[49] Jana, A. K.; Mal, D. Chem. Commun. 2010, 46, 4411.  
[50] Ackermann, L.; Althammer, A. Angew. Chem., Int. Ed. 2007, 46, 1627.  
[51] Abid, M.; Teixeira, L.; T?r?k, B. Tetrahedron Lett. 2007, 48, 4047.  
[52] Lebold, T. P.; Kerr, M. A. Org. Lett. 2008, 10, 997.  
[53] Knott, K. E.; Auschill, S.; Jager, A.; Kn?lker, H. J. Chem. Commun. 2009, 12, 1467.
[54] Eisch, J. J.; Manchanayakage, R. N.; Rheingold, A. L. Org. Lett. 2009, 11, 4060.  
[55] Tanaka, T.; Okunaga, K.; Hayashi, M. Tetrahedron Lett. 2010, 51, 4633.  
[56] Gruner, K. K.; Hopfmann, T.; Matsumoto, K.; Jager, A.; Katsuki, T.; Kn?lker, H. J. Org. Biomol. Chem. 2011, 9, 2057.  
Options
文章导航

/

〈 〉