Synthesis and properties of novel dibenz[b,f]azocines
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.
KeywordsEthyl Hydroxyl Hydrogen Bond Carbonyl Chemical Property
Unable to display preview. Download preview PDF.
- 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.V. A. Kovtunenko, V. M. Kisel', A. K. Tyltin, and F. S. Babichev,Khim. Geterotsikl. Soedin., No. 7, 1000 (1988).Google Scholar
- 3.H. D. Perlmutter and R. B. Trattner,Adv. Heterocyclic Chem.,31, 350 (1982).Google Scholar
- 4.K. Nakanishi,Infrared Spectra and Structure of Organic Compounds [Russian translation], Mir, Moscow (1965), p. 216.Google Scholar
- 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