Download PDF
Synthesis 2005(5): 753-756  
DOI: 10.1055/s-2005-861785
PAPER
© Georg Thieme Verlag Stuttgart · New York

FeCl3-Promoted Intramolecular Annulation of δ-Keto Nitriles: Facile Approach to Prepare 3-Acetamido-2-pyridone Derivatives

Shaozhong Wang*a, Jia Pana, Yuefei Hub, Hongwen Hua
a Department of Chemistry, Nanjing University, Nanjing 210093, P. R. China
Fax: +86(25)83317761; e-Mail: wangsz@nju.edu.cn;
b Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China
Further Information

Publication History

Received 20 October 2004
Publication Date:
18 January 2005 (online)

    Permissions and Reprints All articles of this category

Abstract

A facile approach was developed to synthesize 3-acetamido-2-pyridone derivatives in moderate yields from δ-keto nitriles, derived from Michael addition between ethyl acetamidocyanoacetate and α,β-unsaturated ketones. The tandem reaction sequence promoted by FeCl3 involves intramolecular ketone-nitrile annulation followed by aromatization via selective decarbethoxylation. A plausible mechanism is also described.

Key words

δ-keto nitrile - 3-acetamido-2-pyridone - ferric chloride

    References

  • For natural alkaloids, see:
  • 1a Wall ME. Wani MC. Cook CE. Palmer KH. McPhail AT. Sim GA. J. Am. Chem. Soc.  1966,  88:  3888 
    CrossrefGoogle Scholar
  • 1b Jimenez C. Quinoa E. Adamczeski M. Hunter LM. Crews P. J. Org. Chem.  1991,  56:  3403 
    CrossrefGoogle Scholar
  • 1c Wijeratne EMK. De Silva LB. Kikuchi T. Tezuka Y. Gunatilaka AAL. Kingston DGI. J. Nat. Prod.  1995,  58:  459 
    CrossrefGoogle Scholar
  • 1d Wu T.-S. Chan Y.-Y. Leu Y.-L. Chern C.-Y. Chen C.-F. Phytochemistry  1996,  42:  907 
    CrossrefGoogle Scholar
  • 2a Menta E, Pescalli N, and Spinelli S. inventors; PCT Int. Appl.  WO 0109129.  Chem. Abstr. 2001, 134, 162922
    Crossref
  • 2b Strumberg D. Pommier Y. Paull K. Jayaraman M. Nagafuji P. Cushman M. J. Med. Chem.  1999,  42:  446 
    CrossrefGoogle Scholar
  • 2c Harrison T, Moyes CR, Nadin A, Owens AP, and Lewis RT. inventors; PCT Int. Appl.  WO 9850384.  Chem. Abstr. 1999, 130, 13918
    Crossref
  • 3a Bondavalli F. Bruno O. Presti EL. Menozzi G. Mosti L. Synthesis  1999,  1169 
    CrossrefGoogle Scholar
  • 3b Carles L. Narkunan K. Penlou S. Rousset L. Bouchu D. Ciufolini MA. J. Org. Chem.  2002,  67:  4304 
    CrossrefGoogle Scholar
  • 3c Shimizu M. Ogura K. Hachiya I. Org. Lett.  2003,  4:  2755 
    CrossrefGoogle Scholar
  • 3d Lin CH. Tsai MR. Wang YS. Chang NC. J. Org. Chem.  2003,  68:  5688 
    CrossrefGoogle Scholar
  • 3e Sutherland A. Gallagher T. J. Org. Chem.  2003,  68:  3352 
    CrossrefGoogle Scholar
  • 3f Collins I. Moyes C. Davey WB. Rowley M. Bromidge FA. Quirk K. Atack JR. Mckernan RM. Thompson S.-A. Wafford K. Dawson GR. Pike A. Sohal B. Tsou NN. Ball RG. Castro JL. J. Med. Chem.  2002,  45:  1887 
    CrossrefGoogle Scholar
  • 4a Kranjc A. Peterlin-Masic L. Ilas J. Prezelj A. Stegnar M. Kikelj D. Bioorg. Med. Chem. Lett.  2004,  14:  3251 
    CrossrefGoogle Scholar
  • 4b Peterlin-Masic L. Kranjc A. Marinko P. Mlinsek G. Solmajer T. Stegnar M. Kikelj D. Bioorg. Med. Chem. Lett.  2003,  13:  3171 
    CrossrefGoogle Scholar
  • 5a Dragovich PS. Prins TJ. Zhou R. Johnson TO. Hua Y. Luu HT. Sakata SK. Brown EL. Maldonado FC. Tuntland T. Lee CA. Fuhrman SA. Zalman LS. Patick AK. Matthews DA. Wu EY. Guo M. Borer BC. Nayyar NK. Moran T. Chen L. Rejto PA. Rose PW. Guzman MC. Dovalsantos EZ. Lee S. McGee K. Mohajeri M. Liese A. Tao J. Kosa MB. Liu B. Batugo MR. Gleeson J.-PR. Wu ZP. Liu J. Meador JW. Ferre RA. J. Med. Chem.  2003,  46:  4572 
    CrossrefGoogle Scholar
  • 5b Dragovich PS. Prins TJ. Zhou R. Brown EL. Maldonado FC. Fuhrman SA. Zalman LS. Tuntland T. Lee CA. Patick AK. Matthews DA. Hendrickson TF. Kosa MB. Liu B. Batugo MR. Gleeson J.-PR. Sakata SK. Chen L. Guzman MC. Meador JW. Ferre RA. Worland ST. J. Med. Chem.  2002,  45:  1607 
    CrossrefGoogle Scholar
  • 6a Parlow JJ. Kurumbail RG. Stegeman RA. Stevens AM. Stallings WC. South MS. J. Med. Chem.  2003,  46:  4696 
    CrossrefGoogle Scholar
  • 6b Parlow JJ. South MS. Tetrahedron  2003,  59:  7695 
    CrossrefGoogle Scholar
  • For examples, see:
  • 7a Mckillop A. Boulton AJ. In Comprehensive Heterocyclic Chemistry   Vol. 2:  Katritzky AR. Rees CW. Pergamon; New York: 1984.  Part 2A. p.67 
    Google Scholar
  • 7b Mckillop A. Boulton AJ. In Comprehensive Heterocyclic Chemistry   Vol. 2:  Katritzky AR. Rees CW. Pergamon; New York: 1984.  Part 2A. p.395 
    Google Scholar
  • 8a Reiner JE. Lim-Wilby MS. Brunck TK. Ha-Hong T. Goldman EA. Abelamn MA. Nutt RF. Semple JE. Tamura SY. Bioorg. Med. Chem. Lett.  1999,  9:  895 
    CrossrefGoogle Scholar
  • 8b Isaacs RCA. Cutrona KJ. Newton CL. Sanderson PEJ. Solinsky MG. Baskin EP. Chen I.-W. Cooper CM. Cook JJ. Gardell SJ. Lewis SD. Lucas RJ. Lyle EA. Lynch JJ. Naylor-Olsen AM. Stranieri MT. Vastag K. Vacca JP. Bioorg. Med. Chem. Lett.  1998,  8:  1719 
    CrossrefGoogle Scholar
  • 9a Dragovich PS. Zhou R. Prins TJ. J. Org. Chem.  2002,  67:  741 
    CrossrefGoogle Scholar
  • 9b Tamura SY. Semple JE. Reiner JE. Goldman EA. Brunck TK. Lim-Wilby MS. Carpenter SH. Rote WE. Oldeshulte GL. Richard BM. Nutt RF. Ripka WC. Bioorg. Med. Chem. Lett.  1997,  7:  1543 
    CrossrefGoogle Scholar
  • 10 Yu G. Wang S. Wang K. Hu Y. Hu H. Synthesis  2004,  1021 
    Article in Thieme ConnectGoogle Scholar
  • 11 Wang S. Sun J. Yu G. Hu X. Liu JO. Hu Y. Org. Biomol. Chem.  2004,  2:  1573 
    CrossrefGoogle Scholar
  • 12a Lu J. Bai Y. Wang Z. Yang B. Li W. Synth. Commun.  2001,  31:  2625 
    CrossrefGoogle Scholar
  • 12b Richter DT. Lash TD. Tetrahedron Lett.  1999,  40:  6735 
    CrossrefGoogle Scholar
  • 12c Mueller RH, and Singh J. inventors; Eur. Pat. Appl. EP  575069.  ; Chem. Abstr. 1994, 121, 205123
    Crossref