Download PDF
Synlett 2010(15): 2296-2298  
DOI: 10.1055/s-0030-1258037
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Three-Component Fischer Indole Synthesis

Laurent El Kaïm*, Laurence Grimaud*, Caroline Ronsseray
Laboratoire Chimie et Procédés, Ecole Nationale Supérieure de Techniques Avancées, 32 Bd Victor, 75739 Paris Cedex 15, France
Fax: +33(1)45528322; e-Mail: laurent.elkaim@ensta.fr; e-Mail: laurence.grimaud@ensta.fr;
Further Information

Publication History

Received 24 June 2010
Publication Date:
12 August 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

Three-component coupling between acyl chlorides, diazonium salts, and alcohols or amines allows the formation of α-­hydrazono carboxylic acid derivatives which may be directly converted into indoles by a Fischer-type cylization.

Key words

indoles - Fischer - Japp-Klingeman - diazonium - hydrazone - acid chloride - multicomponent reaction

    References

  • 1a Gribble GW. J. Chem. Soc., Perkin Trans. 1  2000,  1045 
    Google Scholar
  • 1b Sundberg RJ. The Chemistry of Indoles   Academic Press; New York: 1970. 
    Google Scholar
  • 1c Sundberg RJ. Indoles   Academic Press; London: 1996. 
    Google Scholar
  • 1d Humphrey GR. Kuethe JT. Chem. Rev.  2006,  106:  2875 
    Google Scholar
  • 2a Kawasaki T. Higuchi K. Nat. Prod. Rep.  2005,  22:  761 
    Google Scholar
  • 2b Somei M. Yamada F. Nat. Prod. Rep.  2004,  21:  278 
    Google Scholar
  • 3a Fischer E. Jourdan F. Ber. Dtsch. Chem. Ges.  1883,  16:  2241 
    Google Scholar
  • 3b Fischer E. Hess O. Ber. Dtsch. Chem. Ges.  1884,  17:  559 
    Google Scholar
  • 3c Robinson B. The Fischer Indole Synthesis   John Wiley and Sons; Chichester: 1982. 
    Google Scholar
  • 3d Hughes DL. Org. Prep. Proced. Int.  1993,  25:  607 
    Google Scholar
  • For recent reviews, see:
  • 4a Patil S. Buolamwini JK. Curr. Org. Synth.  2006,  3:  477 
    Google Scholar
  • 4b Cacchi S. Fabrizi G. Chem. Rev.  2005,  105:  2873 
    Google Scholar
  • For selected recent examples, see:
  • 4c Jia Y. Zhu J. J. Org. Chem.  2006,  71:  7826 
    Google Scholar
  • 4d Zhao J. Larock R. J. Org. Chem.  2006,  71:  5340 
    Google Scholar
  • For a review, see:
  • 5a Campo J. Garcia-Valverde M. Marcaccini S. Rojo MJ. Torroba T. Org. Biomol. Chem.  2006,  4:  757 
    Google Scholar
  • For recent examples, see:
  • 5b Kalinski C. Umkehrer M. Schmidt J. Ross G. Kolb J. Burdack C. Hiller W. Hoffmann SD. Tetrahedron Lett.  2006,  47:  4683 
    Google Scholar
  • 5c Sunderhaus JD. Dockendorff C. Martin SF. Org. Lett.  2007,  9:  4223 
    Google Scholar
  • 5d Ohno H. Ohta Y. Oishi S. Fujii N. Angew. Chem. Int. Ed.  2007,  46:  2295 
    Google Scholar
  • 5e Barluenga J. Jimenez-Aquino A. Valdes C. Aznar F. Angew. Chem. Int. Ed.  2007,  46:  1529 
    Google Scholar
  • 5f Leogane O. Lebel H. Angew. Chem. Int. Ed.  2008,  47:  350 ; and references cited herein
    Google Scholar
  • 6 Atlan V. El Kaim L. Supiot C. Chem. Commun.  2000,  15:  1385 
    Google Scholar
  • 7a Phillips RR. Org. React.  1959,  60:  144 
    Google Scholar
  • For selected examples of Japp-Klingemann/Fisher indole syntheses, see:
  • 7b Chen Y. Shibata M. Rajeswaran M. Srikrishnan T. Dugare S. Pandey RK. Tetrahedron Lett.  2007,  48:  2353 
    Google Scholar
  • 7c Pete B. Tetrahedron Lett.  2008,  49:  2835 
    Google Scholar
  • 7d Heinrich T. Böttcher H. Bioorg. Med. Chem. Lett.  2004,  14:  2681 
    Google Scholar