Abstract
The catalytic interaction of 5-acetylacenaphthene with arylidene-2-naphthylamines leads to the formation of adducts to the C=N bond (aminoketones) or 1-(5-acenaphthenyl)-3-aryl-(heteroaryl) benzo[f]quinolines. In several instances they are accompanied by 1-(5-acenaphthenyl)-3-R-2-propen-1-ones or N-substituted 2-naphthylamines. The ratio of the products depends on the condensation conditions and the structure of the starting azomethine. Using the 3-(p-fluorophenyl)-substituted derivative as an example, it has been shown that in the absence of dihydrogenating agents Β-aminoketones undergo dehydrocyclization with formation of benzoquinolines and 1,2,3,4-tetrahydroquinolines.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1102–1106, August, 1986
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Kozlov, N.S., Shmanai, G.S. & Tai, D.N. Synthesis and spectral characteristics of acenaphthene derivatives of benzo[f]quinoline. Chem Heterocycl Compd 22, 894–898 (1986). https://doi.org/10.1007/BF01175067
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DOI: https://doi.org/10.1007/BF01175067