Synthesis 2008(9): 1479-1485  
DOI: 10.1055/s-2007-1000936
PSP
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Imidazopyridine Derivatives

Alexis D. C. Parenty*, Leroy Cronin*
WestCHEM, University of Glasgow, Chemistry Department, Glasgow, G12 8QQ, UK
Fax: +44(141)3304888; e-Mail: L.Cronin@chem.gla.ac.uk; e-Mail: Alexisp@chem.gla.ac.uk;
Further Information

Publication History

Received 1 October 2007
Publication Date:
10 January 2008 (eFirst)

Abstract

Two highly efficient and general one-pot annulation reactions are described for the synthesis of imidazopyridine derivatives (IPs). The two procedures are complementary to each other: Whereas the first one allows the production of simpler IPs, the second leads to IPs with functionalized imidazole moiety. Both methodologies consist of an activation step, which raises the electrophilicity of the N-heterocyclic starting material (i.e., quaternarization of the N-heterocycle), followed by a cascade reaction involving nucleophilic addition, substitution, rearrangement, and oxidation steps. These methodologies can be used in the synthesis of a library of drug-like molecules.

    References

  • 1 Comprehensive Heterocyclic Chemistry   Vol. 4:  Katritzky AR. Rees CW. Pergamon Press; New York: 1984.  p.1-38  
  • 2 Tietze LF. Chem. Rev.  1996,  96:  115 
  • 3 Pellisier H. Tetrahedron  2006,  62:  1619 
  • 4 Enders D. Grondal C. Hüttl MRM. Angew. Chem. Int. Ed.  2007,  46:  1570 
  • 5 Nicolaou KC. Edmonds DJ. Bulger PG. Angew. Chem. Int. Ed.  2006,  45:  7134 
  • 6 Parenty ADC. Guthrie KM. Song Y.-F. Smith LV. Burkholder E. Cronin L. Chem. Commun.  2006,  1194 
  • 7 Parenty ADC. Song Y.-F. Richmond CJ. Cronin L. Org. Lett.  2007,  9:  2253 
  • 8 Parenty ADC. Smith LV. Pickering AL. Long DL. Cronin L. J. Org. Chem.  2004,  69:  5934 
  • 9 Parenty ADC. Smith LV. Cronin L. Tetrahedron  2005,  61:  8410 
  • 10a Tóth J. Nedves A. Dancsó A. Blaskó G. Tke L. Nyerges M. Synthesis  2007,  1003 
  • 10b Krauze A. Vitolina R. Garaliene V. Sile L. Klusa V. Duburs G. Eur. J. Med. Chem.  2005,  40:  1163 
  • 10c Fang X. Wu YM. Deng J. Wang SW. Tetrahedron  2004,  60:  5487 
  • 11a Zincke T. Justus Liebigs Ann. Chem.  1903,  330:  361 
  • 11b Zincke T. Justus Liebigs Ann. Chem.  1904,  333:  296 
  • 11c Zincke T. Wurker W. Justus Liebigs Ann. Chem.  1905,  338:  107 
  • 12 Kearney AM. Vanderwal CD. Angew. Chem. Int. Ed.  2006,  45:  7803