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.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 109–113, January, 1991.
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Kisel, V.M., Kovtunenko, V.A., Turov, A.V. et al. Synthesis and properties of novel dibenz[b,f]azocines. Chem Heterocycl Compd 27, 92–95 (1991). https://doi.org/10.1007/BF00633227
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DOI: https://doi.org/10.1007/BF00633227