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Synthesis 2009(8): 1400-1402  
DOI: 10.1055/s-0028-1088009
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© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Gram-Scale Synthesis of Highly Substituted Pyridine Derivatives

Kanniyappan Parthasarathy, Chien-Hong Cheng*
Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan
Fax: +886(3)5724698; e-Mail: chcheng@mx.nthu.edu.tw;
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Publication History

Received 15 November 2008
Publication Date:
06 March 2009 (online)

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Abstract

Rhodium-catalyzed chelation-assisted activation of the β-C-H bond of α,β-unsaturated ketoximes and subsequent reaction with alkynes affords highly substituted pyridine derivatives. This new method provides an opportunity for the one-pot synthesis of pyridines with all five positions (C2-C6) substituted.

Key words

pyridine - ketoxime - rhodium - C-H activation

    References

  • For recent syntheses of highly substituted pyridines, see:
  • 1a Colby DA. Bergman RG. Ellman JA. J. Am. Chem. Soc.  2008,  130:  3645 
    Google Scholar
  • 1b Barluenga J. Fernandez-Rodriguez MA. Garcia-Garcia P. Aguilar E. J. Am. Chem. Soc.  2008,  130:  2764 
    Google Scholar
  • 1c Movassaghi M. Hill MD. Ahmad OK. J. Am. Chem. Soc.  2007,  129:  10096 
    Google Scholar
  • 2a Rama Rao AV. Ravindra Reddy G. Venkateswara Rao B. J. Org. Chem.  1991,  56:  4545 
    Google Scholar
  • 2b Henry GD. Tetrahedron  2004,  60:  6043 
    Google Scholar
  • 2c Michael JP. Nat. Prod. Rep.  2005,  22:  627 
    Google Scholar
  • For reviews, see:
  • 3a Boger DL. J. Heterocycl. Chem.  1998,  35:  1003 
    Google Scholar
  • 3b Zeni G. Larock RC. Chem. Rev.  2004,  104:  2285 
    Google Scholar
  • 3c Varela JA. Saa C. Chem. Rev.  2003,  103:  3787 
    Google Scholar
  • 4a Schiess P. Chia H. Ringele P. Tetrahedron Lett.  1972,  13:  313 
    Google Scholar
  • 4b Tanaka K. Mori H. Yamamoto M. Katsumura S. J. Org. Chem.  2001,  66:  3099 
    Google Scholar
  • 4c Trost BM. Gutierrez AC. Org. Lett.  2007,  9:  1473 
    Google Scholar
  • 5a Varela JA. Castedo L. Saá C. J. Org. Chem.  2003,  68:  8595 
    Google Scholar
  • 5b Sangu K. Fuchibe K. Akiyama T. Org. Lett.  2004,  6:  353 
    Google Scholar
  • 5c Zhang X. Campo MA. Yao T. Larock RC. Org. Lett.  2005,  7:  763 
    Google Scholar
  • 5d McCormick MM. Duong HA. Zuo G. Louie J. J. Am. Chem. Soc.  2005,  127:  5030 ; and references cited therein
    Google Scholar
  • 6 Parthasarathy K. Jeganmohan M. Cheng C.-H. Org. Lett.  2008,  10:  325 
    CrossrefGoogle Scholar
  • 7a Shinada T. Yoshihara K. Tetrahedron Lett.  1995,  36:  6701 
    Google Scholar
  • 7b Booth SE. Jenkins PR. Swain CJ. Sweeney JB. J. Chem. Soc., Perkin Trans. 1  1994,  3499 
    Google Scholar
  • 8a Kakiuchi F. Yamamoto Y. Chatani N. Murai S. Chem. Lett.  1995,  681 
    Google Scholar
  • 8b Jun C.-H. Moon CW. Lee D.-Y. Chem. Eur. J.  2002,  8:  2422 
    Google Scholar
  • 8c Jun C.-H. Moon CW. Kim YM. Lee J. Lee H. Tetrahedron Lett.  2002,  43:  4233 
    Google Scholar
  • 8d Kuninobu Y. Tokunaga Y. Kawata A. Takai K. J. Am. Chem. Soc.  2006,  128:  202 
    Google Scholar
  • 9 Perrin DD. Armarego WLF. Purification of Laboratory Chemicals   3rd ed.:  Pergamon Press; New York: 1988. 
    Google Scholar
  • 10 Osborn JA. Wilkinson G. In Reagents for Transition Metal Complex and Organometallic Syntheses   Vol. 28:  Angelici R. Wiley; New York: 1989.  p.77-79  
    Google Scholar