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Reactions of Bisazomethines of the Naphtalene Series with 1,3-Diketones
Authors:Kozlov  S N  Basalaeva  L I  Ol'khovik  V K  Kalechits  G V  Matveenko  Yu V
Institution:(1) Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk, Belarus;(2) Institite of Chemistry of Novel Materials, National Academy of Sciences of Belarus, Minsk, Belarus
Abstract:Bisazomethines prepared from aromatic dialdehydes and 2-naphthylamine were for the first time reacted with the following diketones: 1,3-cyclohexanedione, 5,5-dimethyl-1,3-cyclohexanedione, 5-phenyl-1,3-cyclohexanedione, indandione, and 2,2-dimethyl-1,3-dioxane-4,6-dione was studied. The reactions with 1,3-diketones of the cyclohexane series yield benzophenanthridine derivatives. The reactions with indandione, depending on conditions, give either bisarylideneindandiones or bisdihydrobenzof]indenoquinoline. As evidenced by the 13C NMR and IR spectra, in the case of biphenyl-4,4'-dicarbaldehyde bisN-(2-naphthyl)imine] and 2,2-dimethyl-1,3-dioxane-4,6-dione, 4,4'-bis(3-oxo-1,2,3,4-tetrahydrobenzof]quinolin-1-yl)biphenyl is formed.
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