Copper(I)-Catalyzed, One-Pot
Synthesis of Multisubstituted Indoles from 2-Iodoanilines
and Ethyl Buta-2,3-dienoate

Xianxue Wang; Jin Liu; Han Guo; Chao Ma; Xiai Gao; Kang Zhou; Guosheng Huang

doi:10.1055/s-0031-1289743

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Synthesis 2012(7): 1037-1042
DOI: 10.1055/s-0031-1289743

PAPER

Copper(I)-Catalyzed, One-Pot Synthesis of Multisubstituted Indoles from 2-Iodoanilines and Ethyl Buta-2,3-dienoate

Xianxue Wang, Jin Liu, Han Guo, Chao Ma, Xiai Gao, Kang Zhou, Guosheng Huang*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: hgs@lzu.edu.cn;

Weitere Informationen

Publikationsverlauf

Received 30 December 2011
Publikationsdatum:
14. März 2012 (online)

Abstract
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Abstract

Reactions of 2-iodoanilines with ethyl buta-2,3-dienoate catalyzed by potassium carbonate and CuI in one pot generate the corresponding ethyl 2-methyl-1H-indole-3-carboxylate products in moderate yields under mild conditions.

Key words

indoles - aniline - allenes - copper - catalysis

References

1a Somei M. Yamada F. Nat. Prod. Rep. 2004, 21: 278

Suche in Google Scholar
1b Somei M. Yamada F. Nat. Prod. Rep. 2005, 22: 73

Suche in Google Scholar
1c Kawasaki T. Higuchi K. Nat. Prod. Rep. 2005, 22: 761

Suche in Google Scholar
1d For the physiological activity of indole derivatives, see: Van Zandt MC. Jones ML. Gunn DE. Geraci LS. Jones JH. Sawicki DR. Sredy J. Jacot JL. DiCioccio AT. Petrova T. Mitschler A. Podjarny AD. J. Med. Chem. 2005, 48: 3141

Suche in Google Scholar
For reports on the total synthesis of indole alkaloids, see:
1e Herzon SB. Myers AG. J. Am. Chem. Soc. 2005, 127: 5342

Suche in Google Scholar
1f Baran PS. Guerrero CA. Hafensteiner BD. Ambhaikar NB. Angew. Chem. Int. Ed. 2005, 44: 3892 ; Angew. Chem. 2005, 117, 3960

Suche in Google Scholar
1g Yamashita T. Kawai N. Tokuyama H. Fukuyama T. J. Am. Chem. Soc. 2005, 127: 15038

Suche in Google Scholar
2a Science of Synthesis Vol. 10: Thomas EJ. Georg Thieme; Stuttgart: 2000.
For some reviews, see:
2b Alonso F. Beletskaya IP. Yus M. Chem. Rev. 2004, 104: 3079

Suche in Google Scholar
2c Nakamura I. Yamamoto Y. Chem. Rev. 2004, 104: 2127

Suche in Google Scholar
2d Cacchi S. Fabrizi G. Chem. Rev. 2005, 105: 2873

Suche in Google Scholar
For some recent indole syntheses, see:
2e Leogane O. Lebel H. Angew. Chem. Int. Ed. 2008, 47: 350 ; Angew. Chem. 2008, 120, 356

Suche in Google Scholar
2f Alex K. Tillack A. Schwarz N. Beller M. Angew. Chem. Int. Ed. 2008, 47: 2304 ; Angew. Chem. 2008, 120, 2337

Suche in Google Scholar
2g Cui S.-L. Wang J. Wang Y.-G. J. Am. Chem. Soc. 2008, 130: 13526

Suche in Google Scholar
2h Bhat V. Allan KM. Rawal VH. J. Am. Chem. Soc. 2011, 133: 5798

Suche in Google Scholar
2i Çelebi-ölçüm N. Boal BW. Huters AD. Garg NK. Houk KN. J. Am. Chem. Soc. 2011, 133: 5752

Suche in Google Scholar
2j Stuart DR. Alsabeh P. Kuhn M. Fagnou K.
J. Am. Chem. Soc. 2010, 132: 18326

Suche in Google Scholar
3a Joule JA. Mills K. Smith GF. Heterocyclic Chemistry Stanley Thornes Ltd.; Cheltenham: 1995.
3b Gilchrist TL. Heterocyclic Chemistry Addison-Wesley Longman Limited; Singapore: 1997.
3c Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 2001, 2491
3d He Z. Li H. Li Z. J. Org. Chem. 2010, 75: 4636

Suche in Google Scholar
3e He Z. Liu W. Li Z. Chem. Asian J. 2011, 6: 1340

Suche in Google Scholar
4 Robinson B. The Fischer Indole Synthesis John Wiley and Sons; New York: 1982.
For recent reviews, see:
5a Cacchi S. Fabrizi G. Chem. Rev. 2011, 111: 215

Suche in Google Scholar
5b Yeung CS. Dong VM. Chem. Rev. 2011, 111: 1215

Suche in Google Scholar
5c Kramer S. Dooleweerdt K. Lindhardt AT. Rottländer M. Skrydstrup T. Org. Lett. 2009, 11: 4208

Suche in Google Scholar
6 Shi Z. Zhang C. Li S. Pan D. Ding S. Cui Y. Jiao N. Angew. Chem. Int. Ed. 2009, 48: 4572

Suche in Google Scholar
7a Würtz S. Rakshit S. Neumann JJ. Dröge T. Glorius F. Angew. Chem. Int. Ed. 2008, 47: 7230

Suche in Google Scholar
7b Bernini R. Fabrizi G. Sferrazza A. Cacchi S. Angew. Chem. Int. Ed. 2009, 48: 8078

Suche in Google Scholar
7c Guan Z.-H. Yan Z.-Y. Ren Z.-H. Liu X.-Y. Liang Y.-M. Chem. Commun. 2010, 46: 2823

Suche in Google Scholar
7d Osuka A. Mori Y. Suzuki H. Chem. Lett. 1982, 2031
7e Bernini R. Cacchi S. Fabrizi G. Filisti E. Sferrazza A. Synlett 2009, 1480
7f Gao D. Parvez M. Back TG. Chem. Eur. J. 2010, 16: 14281

Suche in Google Scholar
7g Chen Y. Xie X. Ma D. J. Org. Chem. 2007, 72: 9329

Suche in Google Scholar
7h Tanimori S. Ura H. Kirihata M. Eur. J. Org. Chem. 2007, 24: 3977

Suche in Google Scholar
8 Mukai C. Takahashi Y. Org. Lett. 2005, 7: 5793

Suche in Google Scholar
9a Yan R. Huang J. Luo J. Wen P. Huang G. Liang Y. Synlett 2010, 1071
9b Yan R. Luo J. Wang CX. Ma CW. Huang G. Liang Y. J. Org. Chem. 2010, 75: 5395

Suche in Google Scholar
9c Ma CW. Li Y. Wen P. Yan R. Ren Z. Huang G. Synlett 2011, 1321
9d Liu J. Wang C. Wu L. Liang F. Huang G. Synthesis 2010, 4228
10 Sugita T. Eida M. Ito H. Komatsu N. Abe K. Suama M. J. Org. Chem. 1987, 52: 3789

Suche in Google Scholar
11a Rout L. Harned AM. Chem. Eur. J. 2009, 15: 12926

Suche in Google Scholar
11b Katoh T. Noguchi C. Kimura H. Fujiwara T. Ichihashi S. Nishide K. Kajimoto T. Node M. Tetrahedron: Asymmetry 2006, 17: 2943

Suche in Google Scholar
12a Reddy KSK. Narender N. Rohitha CN. Kulkarni SJ. Synth. Commun. 2008, 38: 3894

Suche in Google Scholar
12b Robertson WM. Kastrinsky DB. Hwang I. Boger DL. Bioorg. Med. Chem. Lett. 2010, 20: 2722

Suche in Google Scholar