Download PDF
Synthesis 2010(6): 959-966  
DOI: 10.1055/s-0029-1218624
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New, One-Pot, Three-Component, Solvent-Free Synthesis of Amidoalkyl Dibenzofuranols and Dibenzofuran-Condensed 1,3-Oxazin-3-ones

Srinivas Kantevari*, Thirumal Yempala, Srinivasu V. N. Vuppalapati
Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad 500007, India
e-Mail: kantevari@yahoo.com; e-Mail: kantevari@gmail.com;
Further Information

Publication History

Received 6 October 2009
Publication Date:
08 January 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

A new, one-pot, three-component synthesis of amido­alkyl dibenzofuranols and dibenzofuran-condensed 1,3-oxazin-3-ones in good to excellent yields via the reaction of dibenzofuran-2-ol, an aromatic aldehyde, and an amide or urea in the presence of tin(II) chloride dihydrate as a Lewis acid catalyst is described.

Key words

dibenzofuran - multicomponent reaction - amidoalkyl dibenzofuranol - 1,3-oxazin-3-ones - solvent-free - condensation reactions - aromatic aldehyde

    References

  • 1a Multicomponent reactions   Zhu J. Bienaymé H. Wiley-VCH; Weinheim: 2005. 
    Google Scholar
  • 1b von Wangelin AJ. Neumann H. Gordes D. Klaus S. Strubing D. Beller M. Chem. Eur. J.  2003,  9:  4286 
    Google Scholar
  • 1c Dömling A. Chem. Rev.  2006,  106:  17 
    Google Scholar
  • 1d Orru RVA. de Greef M. Synthesis  2003,  1471 
    Google Scholar
  • 1e Hulme C. Gore V. Curr. Med. Chem.  2003,  10:  51 
    Google Scholar
  • 1f Ramón DJ. Yus M. Angew. Chem. Int. Ed.  2005,  44:  1602 
    Google Scholar
  • 2a Ganem B. Acc. Chem. Res.  2009,  42:  463 
    Google Scholar
  • 2b Isambert N. Lavilla R. Chem. Eur. J.  2008,  14:  8444 
    Google Scholar
  • 3a Gao S. Tsai CH. Yao C.-F. Synlett  2009,  949 
    Google Scholar
  • 3b Khosropour AR. Khodaei MM. Moghanian H. Synlett  2005,  955 
    Google Scholar
  • 4a Khodaei MM. Khosropour AR. Moghanian H. Synlett  2006,  916 
    Google Scholar
  • 4b Hajipour AR. Ghayeb Y. Sheikhan N. Ruoho AE. Tetrahedron Lett.  2009,  50:  5649 
    Google Scholar
  • 4c Shaterian HR. Yarahmadi H. Tetrahedron Lett.  2008,  49:  1297 
    Google Scholar
  • 4d Shaterian HR. Yarahmadi H. Ghashang M. Tetrahedron  2008,  64:  1263 
    Google Scholar
  • 4e Shaterian HR. Hosseinian A. Ghashang M. Tetrahedron Lett.  2008,  49:  5804 
    Google Scholar
  • 4f Dorehgiraee A. Khabazzadeh H. Saidi K. ARKIVOC  2009,  (vii):  303 
    Google Scholar
  • 4g Shaterian HR. Hosseinian A. Ghashang M. Bioorg. Med. Chem. Lett.  2008,  18:  788 
    Google Scholar
  • 5a Dabiri M. Delbari AS. Bazgir A. Synlett  2007,  821 
    Google Scholar
  • 5b Dabiri M. Delbari AS. Bazgir A. Heterocycles  2007,  71:  543 
    Google Scholar
  • 6a Kantevari S. Vuppalapati SVN. Nagarapu L. Catal. Commun.  2007,  8:  1857 
    Google Scholar
  • 6b Nagarapu L. Baseeruddin M. Apuri S. Kantevari S. Catal. Commun.  2007,  8:  1729 
    Google Scholar
  • 7 Shakibaei GI. Khavasi HR. Mirzaei P. Bazgir A. J. Heterocycl. Chem.  2008,  45:  1481 
    Google Scholar
  • 8a Rezanka T. Hanus LO. Kujan P. Dembitsky VM. Eur. J. Org. Chem.  2005,  2708 
    Google Scholar
  • 8b Chen J.-J. Luo Y.-T. Liao C.-H. Chen I.-S. Liaw C.-C. Chemistry & Biodiversity  2009,  6:  774 
    Google Scholar
  • 8c Stefano S. Claudio F. Synlett  2003,  2005 
    Google Scholar
  • 8d Kokubun T. Harborne JB. Eagles J. Waterman PG. Phytochemistry  1995,  39:  1033 
    Google Scholar
  • 8e Manniche S. Sprogøe K. Dalsgaard PW. Christophersen C. Larsen TO. J. Nat. Prod.  2004,  67:  2111 
    Google Scholar
  • 9 Prado S. Ledeit H. Michel S. Koch M. Darbord JC. Cole ST. Tillequin F. Brodin P. Bioorg. Med. Chem.  2006,  14:  5423 
    CrossrefPubMedGoogle Scholar
  • 10 Prado S. Janin YL. Saint-Joanis B. Brodin P. Michel S. Koch M. Cole ST. Tillequin F. Bost P.-E. Bioorg. Med. Chem.  2007,  15:  2177 
    CrossrefPubMedGoogle Scholar