Research Progress in Friedel-Crafts Reaction of Indoles and Imines

doi:10.6023/cjoc1103201

Chin. J. Org. Chem. ›› 2012, Vol. ›› Issue (03): 462-471.DOI: 10.6023/cjoc1103201 Previous Articles Next Articles

Reviews

吲哚与亚胺的Friedel-Crafts 反应的研究进展

陈永诚, 解正峰

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 发布日期:2012-03-24
通讯作者: 解正峰 E-mail:xiezhf72@yahoo.com.cn
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

Key Laboratory of Oil & Gas Fine Chemicals Ministry of Education, Xinjiang University, Urumqi 830046

Received:2011-03-20 Revised:2011-09-17 Published:2012-03-24
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20962018, 20862015, 20562011).

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.

Key words: Friedel-Crafts reaction, 3-indolylmethylamine derivative, imine, indole

Cite this article

Chen Yongcheng, Xie Zhengfeng. Research Progress in Friedel-Crafts Reaction of Indoles and Imines[J]. Chin. J. Org. Chem., 2012, (03): 462-471.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.

吲哚与亚胺的Friedel-Crafts 反应的研究进展

Research Progress in Friedel-Crafts Reaction of Indoles and Imines

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[2]	Wenfeng Bei, Jian Pan, Dongmei Ran, Yilin Liu, Zhen Yang, Ruokun Feng. Cobalt-Catalyzed [4+2] Annulation of Indole Carboxamide with Diynes and Monoacetylene: Direct Access to γ-Carbolinones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3226-3238.
[3]	Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu. Synthesis of 3-Trifluoromethylpyrazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3257-3267.
[4]	Junjie Zhang, Xuetao Xu. [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3297-3303.
[5]	Xiaoke Zhang, Xiangru Zheng, Chaoyong Wang. Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3180-3187.
[6]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[7]	Yi Wang, Jian Zhang, Yangzi Liu, Xiaoyan Luo, Weiping Deng. Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2864-2877.
[8]	Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.
[9]	Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li. Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2913-2925.
[10]	Xingxing Yang, Yonghao Fan, Jingjing Cui. Recent Progress in the Main Group Complexes with the 2,6-Pyridinediimine [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2338-2350.
[11]	Lixing Sun, Tingting Sun, Haiqing Wang, Shufang Wu, Xiaoye Wang, Tianya Liu, Yuchen Zhang. Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2178-2188.
[12]	Zeren Sun, Bingxin Zhai, Guangchao He, Hui Shen, Linya Chen, Shan Zhang, Yi Zou, Qihua Zhu, Yungen Xu. Synthesis and Anti-inflammatory Evaluation of Novel 1,2,3-Triazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2143-2155.
[13]	Miaomiao Zhang, Rong Chen, Hongmei Jiao, Haojie Ma, Bo Han, Yuqi Zhang, Jijiang Wang. MgCl₂-Catalyzed Chemoselective Reduction of Aldehydes, Ketones and Imines [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1462-1471.
[14]	Mingyang Pang, Honghong Chang, Zhang Feng, Juan Zhang. Recent Advances in Transition-Metal-Catalyzed Tandem Dearomatization of Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1271-1291.
[15]	Hua Huang, Xin Li, Jianke Su, Qiuling Song. Difluorocarbene-Enabled Synthesis of 3-Substituted-2-oxoindoles from o-Vinylanilines [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1146-1156.