Download PDF
Synthesis 2010(8): 1365-1370  
DOI: 10.1055/s-0029-1218673
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New Synthetic Methodology for Construction of the 1,3,4,5-Tetrahydro-2H-1,3-benzodiazepin-2-one Skeleton

Cagatay Dengiza, Sevil Özcana,b, Ertan Şahinc, Metin Balci*a
a Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey
Fax: +90(312)2103200; e-Mail: mbalci@metu.edu.tr;
b Department of Chemistry, Abant Izzet Baysal University, 14280 Bolu, Turkey
c Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey
e-Mail: ertan@atauni.edu.tr;
Further Information

Publication History

Received 13 December 2009
Publication Date:
11 February 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

We hereby report a new synthetic methodology for construction of the 1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one skeleton. 2-(2-Carboxyethyl)benzoic acid was converted into the corresponding bis(acyl azide). Curtius rearrangement of the diazide followed by reaction with alcohols provided diurethane derivatives. Ring-closure reaction of the diurethanes with base resulted in formation of the 1,3-benzodiazepin-2-one skeleton.

Key words

acyl azide - isocyanate - Curtius rearrangement - urethanes - benzodiazepinone

    References

  • 1a Archer GA. Sternbach LH. Chem. Rev.  1968,  68:  747 
    Google Scholar
  • 1b Sternbach LH. Prog. Drug Res.  1978,  22:  229 
    Google Scholar
  • See, for example:
  • 2a Costa B. Salvetti A. Rossi L. Spinetti F. Lena A. Chelli B. Rechichi M. Da Pozzo E. Gremigni V. Martini C. Mol. Pharmacol.  2006,  69:  37 
    Google Scholar
  • 2b Sternbach LH. J. Med. Chem.  1979,  22:  1 
    Google Scholar
  • 2c Bolli MH. Marfurt J. Grisostomi C. Boss C. Binkert C. Hess P. Treiber A. Thorin E. Morrison K. Buchmann S. Bur D. Ramuz H. Clozel M. Fischli W. Weller T. J. Med. Chem.  2004,  47:  776 
    Google Scholar
  • 2d Torres SRR. Nardi GM. Ferrara P. Ribeiro-do-Valle RM. Farges RC. Eur. J. Pharmacol.  1999,  385:  R1 
    Google Scholar
  • 2e Boojamra CG. Burow KM. Thompson LA. Ellman JA. J. Org. Chem.  1997,  62:  1240 
    Google Scholar
  • 2f Keating TA. Armstrong RW. J. Org. Chem.  1996,  61:  8935 
    Google Scholar
  • 2g Webb RR. Barker PR. Baier M. Reynolds ME. Robarge KD. Blackburn BK. Tichler MH. Weese KJ. Tetrahedron Lett.  1994,  35:  2113 
    Google Scholar
  • 3a inventors; (Boehringer Ingelheim Pharma GmbH & Co. KG, Germany) Eur. Pat. Appl. EP 2065382  A1. 
  • 3b Gottschling D, Dahmann G, Doods H, Heimann A, Mueller SG, Rudolf K, Schaenzle G, and Stenkamp D. inventors; PCT Int. Appl. WO 2009065919  A2. 
  • 3c Nichols PL, Skidmore J, Ward RW, and Wilson DM. inventors; PCT Int. Appl. WO 2009000819  A1. 
  • 3d Schnaubelt J, Stehle E, and Krueger T. inventors; PCT Int. Appl. WO 2007074130  A2. 
  • 4a Yoshida T. Kambe N. Murai S. Sonoda N. Bull. Chem. Soc. Jpn.  1987,  60:  1793 
    Google Scholar
  • 4b Yoshida T. Kambe N. Murai S. Sonoda N. Tetrahedron Lett.  1986,  27:  3037 
    Google Scholar
  • 4c Jen T. Bender P. Van Hoeven H. Dienel B. Loev B. J. Med. Chem.  1973,  16:  407 
    Google Scholar
  • 5 Han X. Civiello RL. Mercer SE. Macor JE. Dubowchik GM. Tetrahedron Lett.  2009,  50:  386 
    CrossrefGoogle Scholar
  • 6 Page GA. Tarbell DS. Org. Synth.   1954,  34:  8 
    Google Scholar
  • 7a Koza G. Ozcan S. Şahin E. Balci M. Tetrahedron  2009,  65:  5973 
    Google Scholar
  • 7b Ozcan S. Balci M. Tetrahedron  2008,  64:  5531 
    Google Scholar
  • 7c Ozcan S. Şahin E. Balci M. Tetrahedron Lett.  2007,  48:  215 
    Google Scholar
  • 8 Murai N. Komatsu M. Yagii T. Nishihara H. Ohshiro Y. Agawa T. J. Org. Chem.  1977,  42:  847 
    CrossrefGoogle Scholar
  • 9a Tsuritani T. Yamamoto Y. Kawasaki M. Mase T. Org. Lett.  2009,  11:  1043 
    Google Scholar
  • 9b Blout ER. Silverman DC. J. Am. Chem. Soc.  1944,  66:  1442 
    Google Scholar
  • 9c Entwistle ID. Tetrahedron Lett.  1979,  555 
    Google Scholar