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Synthesis 2010(18): 3179-3187  
DOI: 10.1055/s-0030-1258180
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Multicomponent Approach for the Synthesis of Phenanthridine and Acridine Ring Systems via the Coupling of Fischer Carbene Complexes with Hetero­aromatic o-Alkynyl Carbonyl Derivatives

Gouranga P. Jana, Soumita Mukherjee, Binay K. Ghorai*
Department of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711103, India
Fax: +91(33)26682916; e-Mail: bkghorai@yahoo.co.in;
Further Information

Publication History

Received 5 May 2010
Publication Date:
16 July 2010 (online)

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Abstract

A one-pot multicomponent synthesis of phenanthridine and acridine derivatives is described. This method includes the in situ generation of furo[3,4-c]isoquinoline and furo[3,4-b]quinoline intermediates by the coupling of heteroaromatic o-alkynyl carbonyl derivatives with Fischer carbene complexes and subsequent trapping of these intermediates by suitable dienophiles.

Key words

azaisobenzofuran - heterocycles - Diels-Alder reaction - chromium - carbene complexes

    References

  • 1a For a review of phenanthridine synthesis, see: Keller PA. In Science of Synthesis   Vol. 15:  StC. Black D. Georg Thieme; Stuttgart: 2005.  Section 15.11. p.1065-1088  
    Google Scholar
  • 1b Balasubramanian M. Keay JG. In Comprehensive Heterocyclic Chemistry II   Vol. 5:  McKillop AE. Katritzky AR. Rees CW. Scriven EFV. Elsevier; Oxford: 1996.  p.245 
    Google Scholar
  • 2 Albert A. The Acridines   2nd ed.:  Edward Arnold Ltd; London: 1966. 
    Google Scholar
  • Some representative phenanthridine syntheses of this century include:
  • 3a Della Ca’ N. Motti E. Catellani M. Adv. Synth. Catal.  2008,  350:  2513 
    Google Scholar
  • 3b Bowman WR. Lyon JE. Pritchard GJ. Synlett  2008,  2169 
    Google Scholar
  • 3c Portela-Cubillo F. Scanlan EM. Scott JS. Walton JC. Chem. Commun.  2008,  4189 
    Google Scholar
  • 3d Marsden SP. McGonagle AE. McKeever-Abbas B. Org. Lett.  2008,  10:  2589 
    Google Scholar
  • 3e Donaldson LR. Haigh D. Hulme AN. Tetrahedron  2008,  64:  468 
    Google Scholar
  • 3f Sripada L. Teske JA. Deiters A. Org. Biomol. Chem.  2008,  6:  263 
    Google Scholar
  • 3g Pandey G. Balakrishnan M. J. Org. Chem.  2008,  73:  8128 
    Google Scholar
  • 3h Buden ME. Rossi RA. Tetrahedron Lett.  2007,  48:  8739 
    Google Scholar
  • 3i Ghorai BK. Duan S. Jiang D. Herndon JW. Synthesis  2006,  3661 
    Google Scholar
  • 3j Shou W.-G. Yang Y.-Y. Wang Y.-G. J. Org. Chem.  2006,  71:  9241 
    Google Scholar
  • 3k Kumemura T. Choshi T. Yukawa J. Hirose A. Nobuhiro J. Hibino S. Heterocycles  2005,  66:  87 
    Google Scholar
  • 3l Ghorai BK. Jiang D. Herndon JW. Org. Lett.  2003,  5:  4261 
    Google Scholar
  • 4a Sourdon V. Mazoyer S. Pique V. Galy J.-P. Molecules  2001,  6:  673 
    Google Scholar
  • 4b Silva TG. Barbosa FSV. Brandao SSF. Lima MCA. Galdino SL. Pitta IR. Barbe J. Heterocycl. Commun.  2001,  7:  523 
    Google Scholar
  • 4c Veverkova E. Noskova M. Toma S. Synth. Commun.  2002,  32:  729 
    Google Scholar
  • 4d Suzuki H. Tanka Y. J. Org. Chem.  2001,  66:  2227 
    Google Scholar
  • 4e Seijas JA. Vazquz-Tato MP. Martinez MM. Rodriguez-Parga J. Green Chem.  2002,  4:  390 
    Google Scholar
  • 4f Goossens R. Smet M. Dehaen W. Tetrahedron Lett.  2002,  43:  6605 
    Google Scholar
  • 4g Laursen BW. Krebs FC. Chem. Eur. J.  2001,  7:  1773 
    Google Scholar
  • 4h Datta I. Das TK. Ghosh SN. Tetrahedron Lett.  1989,  30:  4009 
    Google Scholar
  • 5 Bienayme H. Hulme C. Oddon G. Schmitt P. Chem. Eur. J.  2000,  6:  3321 
    Google Scholar
  • 6 Jana GP. Ghorai BK. Lett. Org. Chem.  2009,  6:  372 
    Google Scholar
  • Isobenzofuran intermediates can be generated using Fischer carbene chemistry.
  • 7a For the first example of this reaction, see: Jiang D. Herndon JW. Org. Lett.  2000,  2:  1267 
    Google Scholar
  • 7b For the latest examples of this reaction, see: Duan S. Sinha-Mahapatra DK. Herndon JW. Org. Lett.  2008,  10:  1541 
    Google Scholar
  • 8 Barbry D. Sokolowski G. Champagne P. Synth. Commun.  2002,  32:  1787 
    CrossrefGoogle Scholar
  • 9 Rüger W. Konz E. Bartmann W. Synthesis  1988,  680 
    Article in Thieme ConnectGoogle Scholar
  • 10 Jana GP. Ghorai BK. Tetrahedron  2007,  63:  12015 
    CrossrefGoogle Scholar
  • 3-Formyl-2-iodoquinoline was prepared from 2-chloro-3-formylquinoline by a halogen-exchange reaction with NaI in acetone; see:
  • 11b 2-Chloro-3-formylquinoline was prepared by the Vilsmeier-Haack reaction of acetanilide with POCl3 and DMF; see: Meth-Cohn O. Narine B. Tarnowski B. J. Chem. Soc., Perkin Trans. 1  1981,  1520 
    Google Scholar
  • 11a Meth-Cohn O. Narine B. Tarnowski B. Hayes R. Keyzad A. Rhouati S. Robinson A. J. Chem. Soc., Perkin Trans. 1  1981,  2509 
    Google Scholar
  • 12a Tobia D. Rickborn B. J. Org. Chem.  1987,  52:  2611 
    Google Scholar
  • 12b Payne AD. Wege D. Org. Biomol. Chem.  2003,  1:  2383 
    Google Scholar
  • 12c Mukherjee S. Jana GP. Ghorai BK.
    J. Organomet. Chem.  2009,  694:  4100 
    Google Scholar
  • 13 Sarkar TK. Panda N. Basak S. J. Org. Chem.  2003,  68:  6919 
    CrossrefGoogle Scholar
  • 14 Li R. Zhang L. Camacho-Davila A. Herndon JW. Tetrahedron Lett.  2005,  46:  5117 
    CrossrefGoogle Scholar
  • 15a For a review on isobenzofurans, see: Friedrichsen W. Adv. Heterocycl. Chem.  1999,  73:  1 
    Google Scholar
  • 15b Rodrigo R. Tetrahedron  1988,  44:  2093 
    Google Scholar
  • 16 Camacho-Davila A. Herndon JW. J. Org. Chem.  2006,  71:  6682 
    CrossrefGoogle Scholar