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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)

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Abstract

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

Key words

GABAA/Bz receptors - imidazo[1,5-a][1,4]benzodiazepines - ethyl isocyanoacetate - annulation

    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 
    CrossrefPubMedSearch in Google Scholar
  • 2 Polc P. Laurent JP. Scherchlicht R. Haefely W. Naunyn Schmiedebergs Arch. Pharmacol.  1981,  316:  317 ; Chem. Abstr. 1981, 95, 143991
    CrossrefPubMedSearch in Google Scholar
  • 3 Hoffman EJ. Warren EW. Clin. Pharm.  1993,  12:  641 
    PubMedSearch in Google Scholar
  • 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
    CrossrefSearch in Google Scholar
  • 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 
    Search in Google Scholar
  • 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 
    Search in Google Scholar
  • 6d Li X. Ma C. He X. Yu J. Han D. Zhang C. Atack JR. Cook JM. Med. Chem. Res.  2002,  11:  504 
    Search in Google Scholar
  • 6e Liu R. Hu RJ. Zhang P. Skolnick P. Cook JM. J. Med. Chem.  1996,  39:  1928 
    Search in Google Scholar
  • 6f Zhang P. Zhang W. Liu R. Harris B. Skolnick P. Cook JM. J. Med. Chem.  1995,  38:  1679 
    Search in Google Scholar
  • 6g Zhang P. Liu R. McKernan RM. Wafford K. Cook JM. Med. Chem. Res.  1995,  5:  487 
    Search in Google Scholar
  • 6h Liu R. Zhang P. McKernan RM. Wafford K. Cook JM. Med. Chem. Res.  1995,  5:  700 
    Search in Google Scholar
  • 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 
    Search in Google Scholar
  • 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 
    Search in Google Scholar
  • 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 
    CrossrefPubMedSearch in Google Scholar