综述与进展

吲哚与亚胺的Friedel-Crafts 反应的研究进展

  • 陈永诚 ,
  • 解正峰
展开
  • 新疆大学石油天然气精细化工教育部重点实验室 乌鲁木齐 830046

收稿日期: 2011-03-20

  修回日期: 2011-09-17

  网络出版日期: 2012-03-24

基金资助

国家自然科学基金(Nos. 20962018, 20862015, 20562011)资助项目.

Research Progress in Friedel-Crafts Reaction of Indoles and Imines

  • Chen Yongcheng ,
  • Xie Zhengfeng
Expand
  • Key Laboratory of Oil & Gas Fine Chemicals Ministry of Education, Xinjiang University, Urumqi 830046

Received date: 2011-03-20

  Revised date: 2011-09-17

  Online published: 2012-03-24

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20962018, 20862015, 20562011).

摘要

由于吲哚类化合物具有许多生物特性等优点, 在众多天然产物和相应的具有生物活性的化合物中起重要的骨架构筑作用, 其合成方法的研究格外令人注目. 近年来, 关于吲哚与亚胺在催化剂作用下发生Friedel-Crafts 反应来制备3-取代吲哚甲胺衍生物的报道剧增. 对近年来吲哚与亚胺Friedel-Crafts 反应的研究情况进行了综述.

本文引用格式

陈永诚 , 解正峰 . 吲哚与亚胺的Friedel-Crafts 反应的研究进展[J]. 有机化学, 2012 , (03) : 462 -471 . DOI: 10.6023/cjoc1103201

Abstract

Indole derivatives have a variety of merits, which have received much attention as building blocks for the synthesis of many natural products and other biologically active compounds. Recently, there are a lot of reports on the synthesis of 3-indolylmethylamine derivatives via the Friedel-Crafts reaction of indoles and imines. The research progress in these catalytic Friedel-Crafts reactions of indoles and imines is reviewed.

参考文献

[1] Poulsen, T. B.; Jorgensen, K. A. Chem. Rev. 2008, 108, 2903.  

[2] Bigi, F.; Casiraghi, G.; Casnati, G.; Sartori, G.; Fava, G. G.; Belicchi,M. F. J. Org. Chem. 1985, 50, 5018.  

[3] Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem.,Int. Ed. 2005, 44, 6576.  

[4] Zheng, C.; Sheng, Y. F.; Li, Y. X.; You, S. L. Tetrahedron 2010, 66,2875.  

[5] Olah, G. A.; Khrisnamurti, R.; Prakash, G. K. S. In ComprehensiveOrganic Synthesis, Vol. 3, Pergamon, New York, 1991, pp. 293~339.  

[6] Sheng, Y. F.; Gu, Q.; Zhang, A. J.; You, S. L. J. Org. Chem. 2009,74, 6899.  

[7] Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem., Int. Ed. 2008, 47,4016.  

[8] Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed.2004, 43, 550.  

[9] Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns, N. Angew.Chem., Int. Ed. 2001, 40, 3284.  

[10] Smith, M. B. Organic Synthesis, McGraw-Hill, New York, 1994, p.1313.

[11] Liu, T. Y.; Cui, H. L.; Chai, Q.; Long, J.; Li, B. J.; Wu, Y.; Ding, L.S.; Chen, Y. C. Chem. Commun. 2007, 43, 2228.

[12] Johnson, J. A.; Ning, L.; Sames, D. J. Am. Chem. Soc. 2002, 124, 6900.  

[13] Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123,4370.  

[14] Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124,1172.  

[15] Marugan, J. J.; Manthey, C.; Anaclerio, B.; Latrance, L.; Lu, T.;Markotan, T.; Leonard, K. A.; Crysler, C.; Eisennagel, S.; Dasgupta,M.; Tomczuk, B. J. Med. Chem. 2005, 48, 926.  

[16] Ramesh, C.; Kavala, V.; Kuo, C. W.; Rama, R. B.; Yao, C. F. Eur. J.Org. Chem. 2010, 2010, 3796.

[17] Zhang, H. C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff,B. E. Org. Lett. 2000, 2, 89.  

[18] Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. J. Org. Chem.1998, 63, 6053.  

[19] Bennasar, M. L.; Vidal, B.; Bosch, J. J. Org. Chem. 1997, 62, 3597.  

[20] Paulvannan, K.; Hale, R.; Mesis, R.; Chen, T. Tetrahedron Lett.2002, 43, 203.  

[21] Furstner, A.; Radkowski, K.; Peters, H. Angew. Chem., Int. Ed.2005, 44, 2777.  

[22] Baran, P. S.; Richter, J. M.; Lin, D. W. Angew. Chem., Int. Ed. 2005,44, 609.  

[23] Zhan, Z. P.; Yang, R. F.; Lang, K. Tetrahedron Lett. 2005, 46, 3859.  

[24] Auria, M. Tetrahedron 1991, 47, 9225.  

[25] Liu, Z.; Shi, M. Tetrahedron: Asymmetry 2009, 20, 119.  

[26] Wang, Y. Q.; Song, J.; Hong, R.; Li, H. M.; Deng, L. J. Am. Chem.Soc. 2006, 128, 8156.  

[27] Johannsen, M. Chem. Commun. 1999, 35, 2233.

[28] Saaby, S.; Fang, X. M.; Gathergood, N.; Jorgensen, K. A. Angew.Chem., Int. Ed. 2000, 39, 4114.  

[29] Saaby, S.; Bayon, P.; Aburel, P. S.; Jorgensen, K. A. J. Org. Chem.2002, 67, 4352.  

[30] Zhuang, W.; Gathergood, N.; Hazell, R. G.; Jorgensen, K. A. J. Org.Chem. 2001, 66, 1009.  

[31] Jia, Y. X.; Xie, J. H.; Duan, H. F.; Wang, L. X.; Zhou, Q. L. Org.Lett. 2006, 8, 1621.  

[32] Ishii, A.; Soloshonok, V. A.; Mikami, K. J. Org. Chem. 2000, 65,1597.  

[33] Gathergood, N.; Zhuang, W.; Jorgensen, K. A. J. Am. Chem. Soc.2000, 122, 12517.  

[34] Lyle, M. P. A.; Draper, N. D.; Wilson, P. D. Org. Lett. 2005, 7, 901.  

[35] Jensen, K. B.; Thorhauge, J.; Hazell, R. G.; Jorgensen, K. A. Angew.Chem. Int. Ed. 2001, 40, 160.  

[36] Zhou, J.; Tang, Y. J. Am. Chem. Soc. 2002, 124, 9030.  

[37] Evans, D. A.; Scheidt, K. A.; Frandrick, K. R.; Lam, H. W.; Wu, J.J. Am. Chem. Soc. 2003, 125, 10780.  

[38] Palomo, C.; Oiarbide, M.; Kardak, B. G.; Garcia, J. M.; Linden, A.J. Am. Chem. Soc. 2005, 127, 4154.  

[39] Evans, D. A.; Fandrick, K. R.; Song, H. J. J. Am. Chem. Soc. 2005,127, 8942.  

[40] Jia, Y. X.; Yang, Y.; Zhu, S. F.; Zhou, Q. L. J. Org. Chem. 2006, 71,75.  

[41] Liu, Z.; Zhang, T.; Shi, M. J. Organomet. Chem. 2008, 27, 2669.

[42] Jorge, E.; Ramon, G. A.; Juan, C. Angew. Chem., Int. Ed. 2006, 45,629.  

[43] Li, B. Y.; Li, Z. J.; Meng, X. B. Carbohydr. Res. 2010, 345, 1708.  

[44] Poulsen, T. B.; Jorgensen, K. A. Chem. Rev. 2008, 108, 2903.  

[45] Qiu, X. L.; Zhu, J. W.; Wu, G. K.; Lee, W. H.; Chamberlin, A. R. J.Org. Chem. 2009, 74, 2018.  

[46] Shirakawa, S.; Kobayashi, S. Org. Lett. 2006, 8, 4939.  

[47] Kang, Q.; Zhao, Z. A.; You, S. L. J. Am. Chem. Soc. 2007, 129,1484.  

[48] Terada, M.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 292.  

[49] Terada, M.; Yokoyama, S.; Sorimachi, K.; Uraguchi, D. Adv. Synth.Catal. 2007, 349, 1863.  

[50] Zhang, G. W.; Wang, L.; Nie, J.; Ma, J. A. Adv. Synth. Catal. 2008,350, 1457.  

[51] Nakamura, S.; Sakurai, Y.; Nakashima, H.; Shibata, N.; Toru, T.Synlett 2009, 1639.

[52] Kang, Q.; Zhao, Z. A.; You, S. L. Tetrahedron 2009, 65, 1603.  

[53] Yang, C. M.; Ni, C. Y.; Liu, Q. Z. Chin. J. Synth. Chem. 2010, 18,184 (in Chinese).(杨彩梅, 倪承燕, 刘全忠, 合成化学, 2010, 18, 184.)

[54] Xu, F. X.; Huang, D.; Han, C.; Shen, W.; Lin, X. F.; Wang, Y. G. J.Org. Chem. 2010, 75, 8677.  

[55] Sun, F. L.; Zheng, X. J.; Gu, Q.; He, Q. L.; You, S. L. Eur. J. Org.Chem. 2010, 2010, 47.

[56] Husmann, R.; Sugiono, E.; Mersmann, S.; Raabe, G.; Rueping, M.;Bolm, C. Org. Lett. 2011, 13, 1044.  

[57] Rueping, M.; Raja, S.; Nunez, A. Adv. Synth. Catal. 2011, 353, 563.  

[58] Lei, F.; Chen, Y. J.; Sui, Y.; Liu, L.; Wang, D. Synlett 2003, 1160.  

[59] Ube, H.; Fukuchi, S.; Terada, M. Tetrahedron: Asymmetry 2010, 21,1203.  

[60] Qian, Y.; Ma, G. Y.; Lv, A. F.; Zhu, H. L.; Zhao, J.; Rawal, V. Chem.Commun. 2010, 46, 3004.  

[61] Yadav, D. K.; Patel, R.; Sivastava, V. P.; Watal, G.; Yadav, L. D. S.Tetrahedron Lett. 2010, 51, 5701.  
文章导航

/