Advertisement

Chemistry of Heterocyclic Compounds

, Volume 27, Issue 1, pp 92–95 | Cite as

Synthesis and properties of novel dibenz[b,f]azocines

  • V. M. Kisel
  • V. A. Kovtunenko
  • A. V. Turov
  • A. K. Tyltin
  • F. S. Babichev
Article

Abstract

5-Acetyl- and 5-trifluoroacetyl-12-hydroxy-11-cyano-5,6-dihydrodibenz[b,f]azocines have been synthesized by intramolecular cyclocondensation of ethyl N-acetyl and N-trifluoroacetyl-N-[1-(cyanomethyl)benzyl]-anthranilates. Spectral data show that the hydroxyl group in 5-acetyl-12-hydroxy-11-cyano-5,6-dihydrodibenz[b,f]azocine takes part in transannular hydrogen bond formation with the acetamide group carbonyl oxygen. A study of the chemical properties of this compound has shown that its alkylation by p, Ω-dibromoacetophenone is accompanied by a Thorpe reaction to form 11-amino-5-acetyl-12-(p-bromo-bemoyl)-5,6-dihydro[b,f]dibenzofuro[2,3-d]azocine.

Keywords

Ethyl Hydroxyl Hydrogen Bond Carbonyl Chemical Property 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature Cited

  1. 1.
    V. M. Kisel', V. A. Kovtunenko, A. V. Turov, A. K. Tyltin, and F. S. Babichev,Dokl. Akad. Nauk SSSR,306, 628 (1989).Google Scholar
  2. 2.
    V. A. Kovtunenko, V. M. Kisel', A. K. Tyltin, and F. S. Babichev,Khim. Geterotsikl. Soedin., No. 7, 1000 (1988).Google Scholar
  3. 3.
    H. D. Perlmutter and R. B. Trattner,Adv. Heterocyclic Chem.,31, 350 (1982).Google Scholar
  4. 4.
    K. Nakanishi,Infrared Spectra and Structure of Organic Compounds [Russian translation], Mir, Moscow (1965), p. 216.Google Scholar
  5. 5.
    R. L. Shriner, R. C. Fuson, D. Y. Curtin, and T. C. Morrill,Identification of Organic Compounds [Russian translation], Mir, Moscow (1988), p. 704.Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • V. M. Kisel
    • 1
  • V. A. Kovtunenko
    • 1
  • A. V. Turov
    • 1
  • A. K. Tyltin
    • 1
  • F. S. Babichev
    • 1
  1. 1.T. G. Shevchenko State UniversityKiev

Personalised recommendations