Synthesis 2003(8): 1201-1208
DOI: 10.1055/s-2003-39402
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Bicyclic Aminoalkyl N-Heterocycles by Ring-Chain-Transformation of Bridged­ 1,3-Dicarbonyl Heteroanalogues with Aminopyrazoles and Aminotriazole­

Magdalena Karanika,b, Michael Pätzela, Jürgen Liebscher*a
a Institut für Chemie, Humboldt-Universität Berlin, Brook-Taylor-Straße 2, 12489 Berlin, Germany
Fax: +49(30)20937552; e-Mail: liebscher@chemie.hu-berlin.de;
b Technical University of Szczecin, Institute of Fundamental Chemistry, Al. Piastow 42, 71-065 Szczecin, Poland
Further Information

Publication History

Received 26 January 2003
Publication Date:
26 May 2003 (online)

Abstract

Reaction of cyclic iminium salts 3 as 1,3-dicarbonyl heteroanalogues with 2-aminoazoles 4 affords bicyclic ω-aminoalkyl N-heterocycles 7 and 11 in a straightforward one-step procedure by a ring-chain-transformation reaction. These products are analogues of interesting pharmaceutical compounds.

    References

  • 1 Pätzel M. Liebscher J. Synthesis  1995,  879 ; and references cited therein
  • 2 Kleeman A. Engel J. Pharmazeutische Wirkstoffe   Thieme; Stuttgart: 1982. 
  • 3 Palazzo G. Tavella M. Strani G. Silvestrini B. J. Med. Chem.  1961,  4:  351 
  • 4 Zelesko MJ. McComsey DF. Hageman WE. Nortey SO. Baker CA. Maryanoff BE. J. Med. Chem.  1983,  26:  230 
  • 5 Pätzel M. Liebscher J. J. Org. Chem.  1992,  57:  1831 
  • 6 Foster AB. Coffey HA. Morin MJ. Rastinejad F. Science  1999,  286:  2507 
  • 7 Calderwood DJ. Johnson DN. Munschauer R. Rafferty P. Bioorg. Med. Chem. Lett.  2002,  12:  1683 
  • 8 Darrow JW, De Lombaert S, Blum C, Tran J, Giangiordano M, Griffith DA, and Carpino PA. inventors; PCT Int. Appl. WO  0123387.  ; Chem. Abstr. 2001, 134, 280866
  • 9 Dionne G. inventors; US  57756501.  ; Chem. Abstr. 1998, 129, 36466
  • 10 Liebscher J. Pätzel M. Kelboro YF. Synthesis  1989,  672 
  • 11 Bohrisch J. Pätzel M. Mügge C. Liebscher J. Synthesis  1991,  1153 ; and references cited therein
  • 12 Jagodziski TS. Chem. Rev.  2003,  103:  197 
  • 13 Hartmann H. Liebscher J. Synthesis  1984,  276 
  • 14 Joshi KC. Pathak VN. Garg U. J. Indian Chem. Soc.  1989,  60:  1074