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Synthesis 2008(22): 3633-3638  
DOI: 10.1055/s-0028-1083198
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient One-Pot Synthesis of 1,3-Disubstituted Pyridin-2(1H)-ones from α-Hydroxyketene S,S-Acetals under Vilsmeier Conditions

Jun Liu, Deqiang Liang, Mang Wang*, Qun Liu*
Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China
Fax: +86(431)85099759; e-Mail: wangm452@nenu.edu.cn;
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Publikationsverlauf

Received 18 June 2008
Publikationsdatum:
23. Oktober 2008 (online)

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Abstract

A facile and efficient one-pot synthesis of 1,3-disubstituted pyridin-2(1H)-ones is developed via a novel cascade reaction of readily available α-hydroxy-α-carbamoyl ketene S,S-acetals under­ Vilsmeier conditions (DMF/POCl3), and a mechanism of this domino reaction is proposed.

Key words

pyridin-2(1H)-ones - Vilsmeier reagent - α-hydroxy­ketene S,S-acetals

    References and Notes

  • 1a Elbein AD. Molyneux RJ. In Alkaloids: Chemical and Biological Perspectives   Vol. 5:  Pelletier SW. Wiley; New York: 1981.  p.1 
    Suche in Google Scholar
  • 1b Li Q. Mitscher LA. Shen LL. Med. Res. Rev.  2000,  20:  231 
    Suche in Google Scholar
  • 1c Nagarajan M. Xiao XS. Antony S. Kohlhagen G. Pommier Y. Cushman M. J. Med. Chem.  2003,  46:  5712 
    Suche in Google Scholar
  • 2a Dolle RE. Nicolaou KC. J. Am. Chem. Soc.  1985,  107:  1691 
    Suche in Google Scholar
  • 2b Cox RJ. O’Hagan D. J. Chem. Soc., Perkin Trans. 1  1991,  2537 
  • 3a Torres M. Gil S. Parra M. Curr. Org. Chem.  2005,  9:  1757 
    Suche in Google Scholar
  • 3b Angibaud PR. Venet MG. Filliers W. Broeckx R. Ligny YA. Muller P. Poncelet VS. End DW. Eur. J. Org. Chem.  2004,  479 
  • 3c Litvinov VP. Russ. Chem. Rev.  2003,  72:  69 
    Suche in Google Scholar
  • 4a Comins DL. Saha JK. J. Org. Chem.  1996,  61:  9623 
    Suche in Google Scholar
  • 4b Du W. Tetrahedron  2003,  59:  8649 
    Suche in Google Scholar
  • 4c Comins DL. Gao JL. Tetrahedron Lett.  1994,  35:  2819 
    Suche in Google Scholar
  • 4d Hu T. Li C. Org. Lett.  2005,  7:  2035 
    Suche in Google Scholar
  • 4e Cristau H.-J. Cellier PP. Spindler J.-F. Taillefer M. Chem. Eur. J.  2004,  10:  5607 
    Suche in Google Scholar
  • 5a Decker H. Ber. Dtsch. Chem. Ges.  1892,  25:  443 
    Suche in Google Scholar
  • 5b Comins DL. Saha JK. J. Org. Chem.  1996,  61:  9623 
    Suche in Google Scholar
  • 6a Baron H. Renfry H. Thorpe J. J. Chem. Soc.  1904,  85:  1726 
    Suche in Google Scholar
  • 6b Aggarwal V. Singh G. Ila H. Junjappa H. Synthesis  1982,  214 
  • 7 Chung KH. Cho KY. Asami Y. Takahashi N. Yoshida S. Heterocycles  1991,  32:  4040 
    Suche in Google Scholar
  • 8a Robin A. Julienne K. Meslin JC. Deniaud D. Tetrahedron Lett.  2004,  45:  9557 
    Suche in Google Scholar
  • 8b Sainte F. Serckx-Poncin B. Hesbain-Frisque A. Ghosez L. J. Am. Chem. Soc.  1982,  104:  1428 
    Suche in Google Scholar
  • 9a Varela JA. Saa C. Chem. Rev.  2003,  103:  3787 
    Suche in Google Scholar
  • 9b Yamamoto Y. Takagishi H. Itoh K. Org. Lett.  2001,  3:  2117 
    Suche in Google Scholar
  • 9c Padwa A. Sheehan SM. Straub CS. J. Org. Chem.  1999,  64:  8648 
    Suche in Google Scholar
  • 9d Padwa A. Heidelbaugh TM. Kuethe JT. J. Org. Chem.  2000,  65:  2368 
    Suche in Google Scholar
  • 10a Pan W. Dong D. Wang K. Zhang J. Wu R. Xiang D. Liu Q. Org. Lett.  2007,  9:  2421 
    Suche in Google Scholar
  • 10b Xiang D. Yang Y. Zhang R. Liang Y. Pan W. Huang J. Dong D. J. Org. Chem.  2007,  72:  8593 
    Suche in Google Scholar
  • 10c Xiang D. Wang K. Liang Y. Zhou G. Dong D. Org. Lett.  2008,  10:  345 
    Suche in Google Scholar
  • 11 Chen L. Zhao Y. Liu Q. Cheng C. Piao C. J. Org. Chem.  2007,  72:  9259 
    CrossrefSuche in Google Scholar
  • 12a Thomas AD. Asokan CV. Tetrahedron Lett.  2002,  43:  2273 
    Suche in Google Scholar
  • 12b Nair SK. Jose AM. Asokan CV. Synthesis  2005,  1261 
  • 12c Asokan CV. Ila H. Junjappa H. Synthesis  1985,  163 
  • 13a Liu J. Wang M. Li B. Liu Q. Zhao Y. J. Org. Chem.  2007,  72:  4401 
    Suche in Google Scholar
  • 13b Liu J. Liang F. Liu Q. Li B. Synlett  2007,  156 
  • 13c Piao C.-R. Zhao Y.-L. Han X.-D. Liu Q. J. Org. Chem.  2008,  73:  2264 
    Suche in Google Scholar
  • 14 Otto M.-C. Bramha N. Brian T. J. Chem. Soc., Perkin Trans.1  1981,  1520 
15

Crystal data for 3a: C14H13NO2S, colorless crystal, M = 259.31, monoclinic, space group P21, a = 5.6429(13), b = 12.163(3), c = 9.504(2), Å, V = 652.3(3) ų, α = 90.00, β = 90.00, γ = 90.00, Z = 2, T = 293 (2) K, F 000 = 272, R1 = 0.0428, wR2 = 0.1077. CCDC 690433 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.