Download PDF
Synthesis 2002(5): 0601-0604
DOI: 10.1055/s-2002-23538
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New Synthesis of 2-Benzazepines

Alan R. Katritzky*, Rexiat Maimait, Yong-Jiang Xu, Rena G. Akhmedova
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA
Fax: +1(352)3929551; e-Mail: katritzky@chem.ufl.edu;
Further Information

Publication History

Received 27 November 2001
Publication Date:
02 April 2002 (online)

    Permissions and Reprints All articles of this category

Abstract

AlCl3-mediated intramolecular cyclization of N,N-bis(1H-1,2,3-benzotriazol-1-ylmethyl)-3-phenyl-1-propanamine (5) gave 2-benzotriazolylmethyl-2,3,4,5-tetrahydro-1H-2-benzazepine (6). Subsequent nucleophilic substitution of the benzotriazolyl group in 6 with Grignard reagents, triethyl phosphite and sodium borohydride afforded 2,3,4,5-tetrahydro-1H-2-benzazepines 1a-e, 2 and 3. Similarly, TiCl4-mediated cyclization of 8 and 10 gave 5,6,7,13b-tetrahydro-9H-isoindolo[1,2-a][2]benzazepin-9-one (9) and 1,2,5,6,7,11b-hexahydro-3H-pyrrolo[2,1-a][2]benzazepin-3-one (11), respectively.

Key words

benzotriazole - 2-benzazepine - cyclization - synthesis

    References

  • 1 Kasparek S. In Advances in Heterocyclic Chemistry   Katritzky AR. Boulton AJ. Academic Press; New York: 1974.  p.45 
    Google Scholar
  • 2a Fuller RW. Molloy BB. Hemrick SK. Biochem. Pharmacol.  1979,  28:  528 
    CrossrefGoogle Scholar
  • 2b Trybulski EJ. Benjamin L. Vitone S. Walser A. Fryer RI. J. Med. Chem.  1983,  26:  367 
    CrossrefGoogle Scholar
  • 2c Trybulski EJ. Fryer RI. Reeder E. Walser A. Blount J. J. Med. Chem.  1983,  26:  1596 
    CrossrefGoogle Scholar
  • 3 Deady LW. Pirzada NH. Topsom RD. J. Chem. Soc., Perkin Trans 1  1973,  782 
    CrossrefGoogle Scholar
  • 4 Orazi OO. Corral RA. Giaccio H. J. Chem. Soc., Perkin Trans. 1  1986,  1977 
    CrossrefGoogle Scholar
  • 5 Grunewald GL. Paradkar VM. Stillions DM. Ching F. J. Heterocycl. Chem.  1991,  28:  1587 
    Google Scholar
  • 6 Jensen BL. Chockalingam K. J. Heterocycl. Chem.  1986,  23:  343 
    Google Scholar
  • 7 Molloy BB. inventors; Canadian Patent  1/119/592.  ; Chem. Abstr. 1982, 97, 388632
  • 8 Grunewald GL. Dahanukar VH. Ching P. Criscione KR. J. Med. Chem.  1996,  39:  3539 
    CrossrefGoogle Scholar
  • 9 Perchonock CD. Lantos I. Finkelstein JA. Holden KG. J. Org. Chem.  1980,  45:  1950 
    Google Scholar
  • 10 Katritzky AR. Xu Y.-J. He H.-Y. Mehta S. J. Org. Chem.  2001,  66:  5590 
    CrossrefGoogle Scholar
  • 11 Katritzky AR. Lan X. Yang JZ. Denisko OV. Chem. Rev.  1998,  98:  409 
    CrossrefPubMedGoogle Scholar
  • 12 Walker GN. Engle AR. Kempton RJ. J. Org. Chem.  1972,  37:  3755 
    Google Scholar