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Synthesis 2010(24): 4273-4281  
DOI: 10.1055/s-0030-1258302
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Conjugate Addition - SNAr Domino Reaction for the Synthesis of Benzo- or Pyridyl-Fused Lactams and Sultams

Niels Grøn Nøragera,b, Karsten Juhl*a
a Medicinal Chemistry Research Denmark, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby, Denmark
Fax: +4536438237; e-Mail: kaju@lundbeck.com;
b Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark
Further Information

Publication History

Received 30 July 2010
Publication Date:
14 October 2010 (online)

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Abstract

A versatile domino reaction that can be used for the synthesis of bicyclic benzo- or pyridyl-fused lactam and sultam derivatives is presented, enabling rapid synthesis of a variety of complex structures.

Key words

bicyclic compounds - domino reactions - heterocycles - Michael addition - nucleophilic aromatic substitution

    References

  • For reviews on domino reactions, see:
  • 1a Padwa A. Bur SK. Tetrahedron  2007,  63:  5341 
    Google Scholar
  • 1b Padwa A. Pure Appl. Chem.  2004,  76:  1933 
    Google Scholar
  • 1c Tietze LF. Chem. Rev.  1996,  96:  115 
    Google Scholar
  • 1d Tietze LF. Angew. Chem., Int. Ed. Engl.  1993,  32:  131 
    Google Scholar
  • 2 Bentley KW. Nat. Prod. Rep.  2000,  17:  247 
    CrossrefGoogle Scholar
  • 3 Glushkov VA. Shklyaev YV. Chem. Heterocycl. Compd.  2001,  37:  663 
    CrossrefGoogle Scholar
  • 4 Pettit GR. Meng YH. Herald DL. Graham KAN. Pettit RK. Doubek DL. J. Nat. Prod.  2003,  66:  1065 
    CrossrefGoogle Scholar
  • 5 Simonsen KB. Juhl K. Steiniger-Brach B. Nielsen SM. Curr. Opin. Drug Discovery Dev.  2010,  13:  379 
    Google Scholar
  • 6 Jayaraman M. Fox BM. Hollingshead M. Kohlhagen G. Pommier Y. Cushman M. J. Med. Chem.  2000,  43:  3688 
    CrossrefGoogle Scholar
  • 7 Busch U. Heinzel G. Narjes H. Nehmiz G. J. Clin. Pharmacol.  1996,  36:  1771 
    Google Scholar
  • 8 Zia-ur-Rehman M. Choudary JA. Ahmad S. Bull. Korean Chem. Soc.  2005,  26:  1771 
    CrossrefGoogle Scholar
  • 9 Lombardino JG. Wiseman EH. McLamore WM.
    J. Med. Chem.  1971,  14:  1171 
    CrossrefGoogle Scholar
  • See for example:
  • 10a Modi AR. Usgaonkar RN. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1979,  18:  304 
    Google Scholar
  • 10b Fisher LE. Muchowski JM. Clark RD. J. Org. Chem.  1992,  57:  2700 
    Google Scholar
  • 10c Davis SE. Church AC. Griffith CL. Beam CF. Synth. Commun.  1997,  27:  2961 
    Google Scholar
  • 10d Jagtap PG. Baloglu E. Southan G. Williams W. Roy A. Nivorozhkin A. Landrau N. Desisto K. Salzman AL. Szabo C. Org. Lett.  2005,  7:  1753 
    Google Scholar
  • 11 Coelho F. Veronese D. Lopes ECS. Rossi RC. Tetrahedron Lett.  2003,  44:  5731 
    CrossrefGoogle Scholar
  • 12 Saeed A. Ashraf Z. Pharm. Chem. J.  2008,  42:  277 
    CrossrefGoogle Scholar
  • See for example:
  • 13a Snow RJ. Butz T. Hammach A. Kapadia S. Morwick TM. Prokopowisc AS. Takahashi H. Tan JD. Tschantz MA. Wang X.-J. Tetrahedron Lett.  2002,  43:  7553 
    Google Scholar
  • 13b Guastavino JF. Barolo SM. Rossi RA. Eur. J. Org. Chem.  2006,  3898 
    Google Scholar
  • See for example:
  • 14a Alonso F. Belatskaya IP. Yus M. Chem. Rev.  2004,  104:  3079 
    Google Scholar
  • 14b Nakamura I. Yamamoto Y. Chem. Rev.  2004,  104:  2127 
    Google Scholar
  • 14c Wang F. Liu H. Fu H. Jiang Y. Zhao Y. Org. Lett.  2009,  11:  2469 
    Google Scholar
  • 14d Wang H. Gao K. Jiang Y. Ma D. Heterocycles  2009,  79:  695 
    Google Scholar
  • 14e Zheng Z. Alper H. Org. Lett.  2008,  10:  4903 
    Google Scholar
  • 15 Zia-ur-Rehman M. Choudary JA. Elsegood MRJ. Siddiqui HL. Kahn KM. Eur. J. Med. Chem.  2009,  44:  1311 
    CrossrefGoogle Scholar
  • 16 Lucilia M. da Mata EN. Motherwell WB. Ujjainwalla F. Tetrahedron Lett.  1997,  38:  137 
    CrossrefGoogle Scholar
  • 17 Rayabarapu DK. Zhou A. Jeon KO. Samarakoon T. Rolfe A. Siddiqui H. Hanson PR. Tetrahedron  2009,  65:  3180 
    CrossrefGoogle Scholar
  • 18 Goossen LJ. Manjolinho F. Khan BA. Rodriguez N. J. Org. Chem.  2009,  74:  2620 
    CrossrefGoogle Scholar
  • 19 Meyer KG. Synlett  2004,  2355 
    Article in Thieme ConnectGoogle Scholar
  • 20 Bouillon A. Lancelot J.-C. Collot V. Bovy PR. Rault S. Tetrahedron  2002,  58:  3323 
    CrossrefGoogle Scholar
  • 21 Gupta L. Hoepker AC. Singh KJ. Collum DB.
    J. Org. Chem.  2009,  74:  2231 
    CrossrefGoogle Scholar