Synthesis 2009(6): 1036-1040  
DOI: 10.1055/s-0028-1083358
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

An Improved Process for the Synthesis of 4H-Imidazo[1,5-a][1,4]benzo­diazepines

Jie Yang, Yun Teng, Shamim Ara, Sundari Rallapalli, James M. Cook*
Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, WI 53211, USA
Fax: +1(414)2295530; e-Mail: capncook@uwm.edu;
Further Information

Publication History

Received 5 September 2008
Publication Date:
11 February 2009 (online)

Abstract

The construction of CNS active imidazo[1,5-a][1,4]benzodiazepines has been improved in a one-pot annulation process.

    References

  • 1 Clayton T. Chen JL. Ernst M. Richter L. Cromer BA. Morton CJ. Ng H. Kaczorowski CC. Helmstetter FJ. Furtmüller R. Ecker G. Parker MW. Sieghart W. Cook JM. Curr. Med. Chem.  2007,  14:  2755 
  • 2 Polc P. Laurent JP. Scherchlicht R. Haefely W. Naunyn Schmiedebergs Arch. Pharmacol.  1981,  316:  317 ; Chem. Abstr. 1981, 95, 143991
  • 3 Hoffman EJ. Warren EW. Clin. Pharm.  1993,  12:  641 
  • 4 inventors; Dutch patent  7803585. F. Hoffmann-La Roche & Co. A.-G., Switzerland ; Chem. Abstr. 1978, 90, 152254
  • 5 Rogers-Evans M. Spurr P. Hennig M. Tetrahedron Lett.  2003,  44:  2425 ; and references cited therein
  • 6a Cook JM, Han D, and Clayton T. inventors; US Patent  2006258643.  ; Chem. Abstr. 2006; 145, 505485
  • 6b Li X. Yu J. Atack JR. Cook JM. Med. Chem. Res.  2004,  13:  259 
  • 6c Li X. Cao H. Zhang C. Furtmueller R. Fuchs K. Huck S. Sieghart W. Deschamps J. Cook JM. J. Med. Chem.  2003,  42:  5567 
  • 6d Li X. Ma C. He X. Yu J. Han D. Zhang C. Atack JR. Cook JM. Med. Chem. Res.  2002,  11:  504 
  • 6e Liu R. Hu RJ. Zhang P. Skolnick P. Cook JM. J. Med. Chem.  1996,  39:  1928 
  • 6f Zhang P. Zhang W. Liu R. Harris B. Skolnick P. Cook JM. J. Med. Chem.  1995,  38:  1679 
  • 6g Zhang P. Liu R. McKernan RM. Wafford K. Cook JM. Med. Chem. Res.  1995,  5:  487 
  • 6h Liu R. Zhang P. McKernan RM. Wafford K. Cook JM. Med. Chem. Res.  1995,  5:  700 
  • 7a Watjen F. Baker R. Engelstoff M. Herbert R. MacLeod A. Knight A. Merchant K. Moseley J. Saunders J. J. Med. Chem.  1989,  32:  2282 
  • 7b Fryer IR, and Walser A. inventors; Eur. Patent  135770.  ; Chem. Abstr. 1985, 103, 160545
  • 7c Fryer IR. Gu Z.-Q. Wang C.-G. J. Heterocycl. Chem.  1991,  28:  1661 
  • 8 Anzini M. Braile C. Valenti S. Cappelli A. Vomero S. Marinelli L. Limongelli V. Novellino E. Betti L. Giannaccini G. Lucacchini A. Ghelardini C. Norcini M. Makovec F. Giorgi G. Fryer IR. J. Med. Chem.  2008,  51:  4730