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Synthesis 2011(1): 23-29  
DOI: 10.1055/s-0030-1258348
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© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Preparation of Polyfunctional Indoles via a Zinc Organometallic Variation of the Fischer Indole Synthesis

Zhi-Guang Zhanga,b, Benjamin A. Haaga, Jin-Shan Lib, Paul Knochel*a
a Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 Munich, Germany
Fax: +49(89)218077680; e-Mail: paul.knochel@cup.uni-muenchen.de;
b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China
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Publication History

Received 28 October 2010
Publication Date:
03 December 2010 (online)

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Abstract

Functionalized organozinc reagents readily react with various aryldiazonium salts furnishing regioselectively polyfunctional indoles after heating with microwave irradiation. This new organometallic variation of the Fischer indole synthesis tolerates a wide range of functional groups and can be readily scaled up.

Key words

organozinc reagents - indoles - regioselectivity - Fischer indole synthesis - N-heterocycles

    References

  • 1a Sundberg RT. Indoles   Academic Press; London: 1996. 
  • 1b Comprehensive Heterocyclic Chemistry II   Vol. 2:  Katritzky AR. Rees CW. Scriven EFV. Pergamon Press; Oxford: 1996.  p.207-257  
  • 1c Sundberg RJ. In Comprehensive Heterocyclic Chemistry II   Vol. 2:  Katritzky AR. Ress CW. Scriven EFV. Bird CW. Pergamon Press; Oxford: 1996. 
    Search in Google Scholar
  • 1d Joule A. In Science of Synthesis   Vol. 10:  Thomas EJ. Thieme; Stuttgart: 2000.  Chap. 10.13.
    Search in Google Scholar
  • 2a Humphrey GR. Kuethe JT. Chem. Rev.  2006,  106:  2875 
    Search in Google Scholar
  • 2b Zeni G. Larock RC. Chem. Rev.  2004,  104:  2285 
    Search in Google Scholar
  • 3 Cacchi S. Fabrizi G. Chem. Rev.  2005,  105:  2873 
    CrossrefPubMedSearch in Google Scholar
  • 4a Fischer E. Jourdan F. Ber. Dtsch. Chem. Ges.  1883,  16:  2241 
    Search in Google Scholar
  • 4b Robinson B. The Fischer Indole Synthesis   Wiley-Interscience; New York: 1982. 
  • 5 Handbook of Functionalized Organometallics   Knochel P. Wiley-VCH; Weinheim: 2005. 
  • 6 Haag BA. Zhang Z.-G. Li J.-S. Knochel P. Angew. Chem. Int. Ed.  2010,  49: in press; DOI: anie.201005319
    Search in Google Scholar
  • 7 Erdik E. Organozinc Reagents in Organic Synthesis   CRC-Press; Boca Raton: 1996. 
  • 8a Dong Z. Manolikakes G. Li J. Knochel P. Synthesis  2009,  681 
  • 8b Despotopoulou C. Gignoux C. McConnell D. Knochel P. Synthesis  2009,  3661 
  • 8c Monzon G. Knochel P. Synlett  2010,  304 
  • 8d Metzger A. Argyo C. Knochel P. Synthesis  2010,  882 
  • 9 Krasovskiy A. Malakhov V. Gavryushin A. Knochel P. Angew. Chem. Int. Ed.  2006,  45:  6040 
    CrossrefPubMedSearch in Google Scholar
  • 10a Piller FM. Appukkuttan P. Gavryushin A. Helm M. Knochel P. Angew. Chem. Int. Ed.  2008,  47:  6802 
    Search in Google Scholar
  • 10b Piller FM. Metzger A. Schade MA. Haag BA. Gavryushin A. Knochel P. Chem. Eur. J.  2009,  15:  7192 
    Search in Google Scholar
  • 11a Haag BA. Peng Z. Knochel P. Org. Lett.  2009,  11:  4270 
    Search in Google Scholar
  • 11b Sapountzis I. Knochel P. Angew. Chem. Int. Ed.  2004,  43:  897 
    Search in Google Scholar
  • 12a Rice LM. Hertz E. Freed ME. J. Med. Chem.  1964,  7:  313 
    Search in Google Scholar
  • 12b Baxter BL. Gluckman MI. Nature  1969,  223:  750 
    Search in Google Scholar
  • 13 Chen J. Hu Y. Synth. Commun.  2006,  36:  1485 
    CrossrefSearch in Google Scholar