Download PDF
Synthesis 2004(7): 1021-1028  
DOI: 10.1055/s-2004-822325
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Novel Approach to 1,2-Dihydro-2-Oxo-3-Pyridinecarboxylic Ester via Aromatization Induced by Deamidation

Gang Yua, Shaozhong Wanga, Kai Wanga, Yuefei Hu*a,b, Hongwen Hua
a Department of Chemistry, Nanjing University, Nanjing 210093, P. R. China
b Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China
Fax: +86(25)83317761; e-Mail: yfh@mail.tsinghua.edu.cn;
Further Information

Publication History

Received 24 December 2003
Publication Date:
02 April 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

A novel approach was developed for the preparation of 4,6-disubstituted-1,2-dihydro-2-oxo-3-pyridinecarboxylic ester in moderate to good yields. This route involves a reaction sequence of Michael addition, transformation to ene-lactam, and aromatization, featuring easily available material, variable substituents, and good functional compatibility.

Key words

synthesis - ethyl acetamidocyanoacetate - aromatization via deamidation - sodium carbonate - 4,6-disubstituted-1,2-dihydro-2-oxo-3-pyridinecarboxylic ester

    References

  • 1a Morimoto K, Furusawa H, Terachi T, Nawamki T, Watanabe S, Nakahira K, and Noguchi J. inventors; PCT Int. Appl. WO  9857957.  ; Chem. Abstr. 1999, 130, 66511b
  • 1b Miyazaki M, Matsuzawa M, Toriyabe K, and Hirata M. inventors; Jpn. Kokai Tokkyo Koho JP  0641116.  ; Chem. Abstr. 1994, 121, 57525w
  • 2a Sanderson PE, Naylor-Olsen AM, Dyer DL, Vacca JP, Isaacs RCA, Dorsey BD, and Fraley ME. inventors; US Patent  5,668,289.  ; Chem. Abstr. 1997, 127, 293131j
  • 2b Bernstein PR, Shaw A, Thomas RM, Warner P, and Wolanin DJ. inventors; US Patent  5,521,179.  ; Chem. Abstr. 1996, 125, 247628n
  • 3a Piazza G, and Pamukcu R. inventors; US Patent  6,046,216.  ; Chem. Abstr. 2000, 132, 251078v
  • 3b Liverton NJ, Claremon DA, Butcher JW, and Theberge CR. inventors; PCT Int. Appl. WO  0100208.  ; Chem. Abstr. 2001, 134, 86270h
  • 4a Mariella RP. Havlik AJ. J. Am. Chem. Soc.  1952,  74:  1915 
    CrossrefSearch in Google Scholar
  • 4b Mariella RP. Belcher EP. J. Am. Chem. Soc.  1951,  73:  2616 
    CrossrefSearch in Google Scholar
  • 5a Bondavalli F. Bruno O. Presti EL. Menozzi G. Mosti L. Synthesis  1999,  1169 
  • 5b Ito K. Yokokura S. Miyajima S. J. Heterocycl. Chem.  1989,  27:  773 
    Search in Google Scholar
  • 5c Alberola A. Andres C. Ortega AG. Pedrosia R. Vicente M. J. Heterocycl. Chem.  1987,  24:  709 
    Search in Google Scholar
  • 5d Osman AN. Ismail MM. Barakat MA. Egypt J. Pharm. Sci.  1987,  29:  87 ; Chem. Abstr. 1987, 106, 119644k
    Search in Google Scholar
  • 6a Caille JC. Didierlaurent S. Leftrancois D. Lelievre MH. Sury C. Aszodi J. Synthesis  1995,  635 
  • 6b Logemann FI. Shaw G. Chem. Ind. (London)  1980,  541 
  • 6c Conard M. Schulze A. Ber. Dtsch. Chem. Ges.  1909,  42:  736 
    Search in Google Scholar
  • 7 Owen AM. Donald TW. J. Am. Chem. Soc.  1948,  70:  2763 
    CrossrefSearch in Google Scholar
  • 8a Mukund PS. Shankar M. Tetrahedron  2000,  56:  8033 
    Search in Google Scholar
  • 8b Lakhlifi T. Sedgui A. Fathi T. Laude B. Robert JF. Can. J. Chem.  1994,  82:  1417 
    Search in Google Scholar
  • 9a Murahashi SI. Sasao S. Saito E. Naota T. J. Org. Chem.  1992,  58:  2521 
    CrossrefSearch in Google Scholar
  • 9b Murahashi SI. Sasao S. Saito E. Naota T. Tetrahedron  1993,  49:  8805 
    CrossrefSearch in Google Scholar
  • 10 Zhang Z. Gao S. Sun Q. Sun Y. Mao L. Youji Huaxue  1993,  49:  8805 
    Search in Google Scholar
  • 11 Mao L. Gao S. Zhang Z. Sun Q. Sun Y. Chin. Chem. Lett.  1994,  11:  921 
    Search in Google Scholar
  • 12a Kunstmann R. Lerch U. Wagner K. J. Heterocycl. Chem.  1981,  19:  1437 
    Search in Google Scholar
  • 12b Kunstmann R. Lerch U. Gerhards H. Leven M. Schacht U. J. Med. Chem.  1984,  28:  432 
    Search in Google Scholar
  • 13a Gurjar M. Reddy DS. Murugaiah A. Murugaiah S. Synthesis  2000,  1659 
    Thieme Connect
  • 13b Krapcho AP. Synthesis  1982,  893 
    Thieme Connect
  • 13c Krapcho AP. Synthesis  1982,  805 
    Thieme Connect
  • 14 Wang S. Yu G. Lu J. Xiao K. Hu Y. Hu H. Synthesis  2003,  487 
    Thieme Connect
  • 15a Sano T. Horiguchi Y. Tsuda Y. Chem. Pharm. Bull.  1990,  39:  3283 
    Search in Google Scholar
  • 15b Sano T. Horiguchi Y. Tanaka K. Tsuda Y. Chem. Pharm. Bull.  1990,  39:  36 
    Search in Google Scholar
  • 16 Kuthan J. Nesvadba P. Popl M. Fahnrich J. Collect. Czech. Chem. Commun.  1979,  44:  2409 
    CrossrefSearch in Google Scholar
  • 17a Popandova-Yambolieva K. Synthesis  1990,  85 
    Thieme Connect
  • 17b Singh B. Synthesis  1985,  305 
    Thieme Connect
  • 18 Carles L. Narkunan K. Penlou S. Rousset L. Bouchu D. Ciufolini MA. J. Org. Chem.  2002,  67:  4304 
    CrossrefSearch in Google Scholar