Download PDF
Synthesis 2010(24): 4207-4212  
DOI: 10.1055/s-0030-1258311
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Iron/Palladium-Catalyzed Intramolecular Hydroamination: An Expedient Synthesis of Pyrrole-Annulated Coumarin and Quinolone Derivatives

K. C. Majumdar*, Nirupam De, B. Roy
Department of Chemistry, University of Kalyani, Kalyani 741235, W.B., India
Fax: +91(33)925828282; e-Mail: kcm_ku@yahoo.co.in;
Further Information

Publication History

Received 30 August 2010
Publication Date:
21 October 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

A highly efficient intramolecular hydroamination reaction of heterocycle-centered aminoalkynes using both substituted and free amines catalyzed by PdCl2/FeCl3 catalytic system to form the biologically important pyrrolocoumarin and pyrroloquinolone derivatives is reported. The use of both aliphatic and aromatic substituted alkynes with different heterocyclic skleton in this strategy demonstrated the diversity of this method.

Key words

hydroamination - pyrrolocoumarin - pyrroloquinolone - FeCl3 - aminoalkynes

    References

  • 1a Glasby JS. Encyclopedia of Alkaloids   Plenum Press; New York: 1975. 
    Google Scholar
  • 1b Cacchi S. Fabrizi G. Chem. Rev.  2005,  105:  2873 
    Google Scholar
  • 1c Li JJ. Gribble GW. Palladium in Heterocyclic Chemistry   Pergamon; Oxford: 2000.  Chap. 3.
    Google Scholar
  • 1d Somei M. Yamada F. Nat. Prod. Rep.  2005,  22:  73 
    Google Scholar
  • 2a Arcadi A. Bianchi G. Marinelli F. Synthesis  2004,  610 
    Google Scholar
  • 2b Zhang Y. Donahue JP. Li C.-J. Org. Lett.  2007,  9:  627 
    Google Scholar
  • 2c Sakai N. Annaka K. Konakahara T. Tetrahedron Lett.  2006,  47:  631 
    Google Scholar
  • 2d Namba K. Nakagawa Y. Yamamoto H. Imagawa H. Nishizawa M. Synlett  2008,  1719 
    Google Scholar
  • 2e Li X. Chianese AR. Vogel T. Crabtree RH. Org. Lett.  2005,  7:  5437 
    Google Scholar
  • 3a Hagen SE. Domagala JM. Heifetz CL. Sanchez JP. Solomon M. J. Med. Chem.  1990,  33:  849 
    Google Scholar
  • 3b Raski SR. Williams RM. Chem. Rev.  1998,  98:  2723 
    Google Scholar
  • 3c Murakami A. Gao G. Omura M. Yano M. Ito C. Furukawa H. Takahasi D. Koshimizu K. Ohigash H. Biorg. Med. Chem. Lett.  2000,  10:  59 
    Google Scholar
  • 3d Laborde E. Kiely JS. Culbertson TP. Lesheski LE. J. Med. Chem.  1993,  36:  1964 
    Google Scholar
  • 4a Dickinson JM. Nat. Prod. Rep.  1993,  10:  71 
    Google Scholar
  • 4b Piorung MC. Blume F. J. Org. Chem.  1999,  64:  3642 
    Google Scholar
  • 4c Boyd DR. Sharma ND. Barr SA. Carroll JG. Mackerracher D. Malone JF. J. Chem. Soc., Perkin Trans. 1  2000,  3397 
    Google Scholar
  • 5a Rodighiero P. Chilin A. Pastorini G. Guiotto A.
    J. Heterocycl. Chem.  1987,  24:  1041 
    Google Scholar
  • 5b Guiotto A. Chilin A. Manzini P. Dall’Acqua F. Bordin F. Rodighiero P. Farmaco  1995,  50:  479 
    Google Scholar
  • 6 Gia O. Mobilio S. Chilin A. Rodghiero P. Palumbo M. J. Photochem. Photobiol., B.  1988,  2:  435 
    CrossrefGoogle Scholar
  • 7 Quanten E. Adriaens P. Schryver FC. Roelandts R. Degreef H. Photochem. Photobiol.  1986,  43:  485 
    CrossrefGoogle Scholar
  • 8 Kontogiorgis C.  Litinas KE. Makri A.  Nicolaides DN.  Vronteli A.  Litina DJH. Pontiki E. Siohou A.
    J. Enzyme Inhib. Med. Chem.  2008,  23:  43 
    CrossrefPubMedGoogle Scholar
  • 9 Chen L. Hu T.-S. Yao Z.-J. Eur. J. Org. Chem.  2008,  36:  6175 
    Google Scholar
  • 10 Chen L. Xu MH. Adv. Synth. Catal.  2009,  351:  2005 
    CrossrefGoogle Scholar
  • 11a Ridley CP. Reddy MVR. Rocha G. Bushman FD. Faulknera DJ. Bioorg. Med. Chem.  2002,  10:  3285 
    Google Scholar
  • 11b Fan H. Peng J. Hamann MT. Hu JH. Chem. Rev.  2008,  108:  264 
    Google Scholar
  • 11c Yamaguchi T. Fukuda T. Ishibashi F. Iwao M. Tetrahedron Lett.  2006,  47:  3755 
    Google Scholar
  • 11d Tardy C. Facompre M. Laine W. Baldeyrou B. Garcia-Gravalos D. Francesch A. Mateo C. Pastor A. Jimenez JA. Manzanares I. Cuevasb C. Bailly C. Bioorg. Med. Chem.  2004,  12:  1697 
    Google Scholar
  • 12a Jiang W. Alford VC. Qiu Y. Bhattacharjee S. John TM. Johnson DH. Kraft PJ. Lundeen SG. Sui Z. Bioorg. Med. Chem.  2004,  12:  1505 
    Google Scholar
  • 12b Yamashkin SA. Yudin LG. Kost AN. Chem. Heterocycl. Compd. (Engl. Transl.)  1983,  19:  401 
    Google Scholar
  • 13 Ho TCT. Jones K. Tetrahedron  1997,  53:  8287 
    CrossrefGoogle Scholar
  • 14a Majumdar KC. Mondal S. De N. Synlett  2008,  2851 
    Google Scholar
  • 14b Majumdar KC. Mondal S. De N. Synthesis  2009,  2385 
    Google Scholar
  • 14c Majumdar KC. Chattopadhyay B. Samanta S. Synthesis  2009,  311 
    Google Scholar
  • 14d Majumdar KC. Chakravorty S. De N. Tetrahedron Lett.  2008,  49:  3419 
    Google Scholar
  • 14e Majumdar KC. Samanta S. Chattopadhyay B. Tetrahedron Lett.  2008,  49:  7213 
    Google Scholar
  • 15a Tang Z.-Y. Hu O.-S. Adv. Synth. Catal.  2006,  348:  846 
    Google Scholar
  • 15b Kaspar LT. Ackermann L. Tetrahedron  2005,  61:  11311 
    Google Scholar
  • 15c Yasuhara A. Takeda Y. Naoyuki S. Sakamoto T. Chem. Pharm. Bull.  2002,  50:  235 
    Google Scholar
  • 16a Zhang Y. Donahue JP. Li C.-J. Org. Lett.  2007,  9:  627 
    Google Scholar
  • 16b Kurisaki T. Naniwa T. Yamamoto H. Imagawa H. Nishizawa M. Tetrahedron Lett.  2007,  48:  1871 
    Google Scholar
  • 16c Hiroya K. Itoh S. Ozawa M. Kanamori Y. Sakamoto T. Tetrahedron Lett.  2002,  43:  1277 
    Google Scholar
  • 16d Yin Y. Chai Z. Ma W.-Y. Zhao G. Synthesis  2008,  4036 
    Google Scholar
  • 16e Trost BM. McClory A. Angew. Chem. Int. Ed.  2007,  46:  2074 
    Google Scholar
  • 16f Cariou K. Ronan B. Mignani S. Fensterbank L. Malacria M. Angew. Chem. Int. Ed.  2007,  46:  1881 
    Google Scholar
  • 17 Koradin C. Dohale W. Rodriguez AL. Schmidt B. Knochel P. Tetrahedron  2003,  59:  1571 
    CrossrefGoogle Scholar
  • 18 Terrasson V. Michaux J. Gaucher A. Wehbe J. Marque S. Prim D. Campagne J.-M. Eur. J. Org. Chem.  2007,  35:  5332 
    Google Scholar
  • 19 Liang Y. Tang S. Zhang X.-D. Mao L.-Q. Xie Y.-X. Li J.-H. Org. Lett.  2006,  8:  3017 
    CrossrefGoogle Scholar
  • 20 Tang S. Xie Y.-X. Li J.-H. Wang N.-X. Synthesis  2007,  1841 
    Article in Thieme ConnectGoogle Scholar
  • 21 Baldwin JE. J. Chem. Soc., Chem. Commun.  1976,  734 
    CrossrefGoogle Scholar