Efficient Synthesis of 9H-Pyrrolo[1,2-α]Indoles via Michael Addition–Condensation of 3-Substituted Indoles with α,β-Unsaturated Ketimines
Minmin Zhang
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorLihua Liao
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorShuowen Yu
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorYijun Liao
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorXiaoying Xu
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
Search for more papers by this authorWeicheng Yuan
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
Search for more papers by this authorCorresponding Author
Xiaomei Zhang
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
E-mail: [email protected]Search for more papers by this authorMinmin Zhang
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorLihua Liao
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorShuowen Yu
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorYijun Liao
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorXiaoying Xu
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
Search for more papers by this authorWeicheng Yuan
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
Search for more papers by this authorCorresponding Author
Xiaomei Zhang
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
E-mail: [email protected]Search for more papers by this authorAbstract
By employing copper dibromide as a catalyst, Michael addition–condensation of 3-substituted indoles with α,β-unsaturated ketimines was realized. The reactions afforded a large variety of 9H-pyrrolo[1,2-α]indoles with good yields (up to 99 %). In addition, a plausible reaction mechanism was proposed.
References and Notes
- 1(a) Mazzola, V. J.; Bernady, K. F.; Franck, R. W. J Org Chem 1967, 32, 486; (b) Verboom, W.; Lammerink, B. H. M.; Egberink, R. J. M.; Reinhoudt, D. N.; Harkema, S. J Org Chem 1985, 50, 3797; (c) Fogassy, K.; Kovacs, K.; Keseru, G. M.; Toke, L.; Faigl, F. J Chem Soc Perk T 2001, 1, 1039.
- 2For some recent references about synthesis of 9H-pyrrolo[1,2-α]indoles, see:(a) Li, H.; Wang, Z.; Zu, L. RSC Adv 2015, 5, 60962; (b) Liu, H. Q.; El-Salfiti, M.; Lautens, M. Angew Chem Int Edit 2012, 51, 9846; (c) Kobayashi, K.; Hashimoto, K.; Hashimoto, H.; Kondo, H.; Konishi, H. Helv Chim Acta 2011, 94, 1277; (d) Kobayashi, K.; Himei, Y.; Fukamachi, S.; Tanmatsu, M.; Morikawa, O.; Konishi, H. Tetrahedron 2007, 63, 4356; (e) Hao, L.; Pan, Y. M.; Wang, T.; Lin, M.; Chen, L.; Zhan, Z. P. Adv Synth Catal 2010, 352, 3215; (f) Aiello, F.; Garofalo, A.; Grande, F. Tetrahedron Lett 2010, 51, 6635; (g) Aiello, F.; Garofalo, A.; Grande, F. Tetrahedron 2010, 66, 274; (h) Wood, K.; Black, D. S.; Kumar, N. Tetrahedron Lett 2009, 50, 574; (i) Hwang, S. J.; Cho, S. H.; Chang, S. J Am Chem Soc 2008, 130, 16158; (j) Ren, H. J.; Knochel, P. Angew Chem Int Ed 2006, 45, 3462; (k) Feldman, K. S.; Iyer, M. R.; Hester, D. K. Org Lett 2006, 8, 3113.
- 3(a) Cheng, H. G.; Lu, L. Q.; Wang, T.; Yang, Q. Q.; Liu, X. P.; Li, Y.; Deng, Q. H.; Chen, J. R.; Xiao, W. J. Angew Chem Int Ed 2013, 52, 3250; (b) Angelovski, G.; Keranen, M. D.; Linnepe, P.; Grudzielanek, S.; Eilbrachta, P. Adv Synth Catal 2006, 348, 1193; (c) Du, Y.; Huang, H. Y.; Liu, H.; Ruan, Y. P.; Huang, P. Q. Synlett 2011 565; (d) Nguyen, H.; Ma, G.; Gladysheva, T.; Fremgen, T.; Romo, D. J Org Chem 2011, 76, 2.
- 4(a) Espinosa, M.; Blay, G.; Cardona, L.; Pedro, J. R. Chem Eur J 2013, 19, 14861; (b) Stark, D. G.; Morrill, L. C.; Yeh, P. P.; Slawin, A. M. Z.; Riordan, T. J. C. O.; Smith, A. D. Angew Chem Int Ed 2013, 52, 11642.