Chemistry of Heterocyclic Compounds p. 846 - 849 (1987)
Update date:2022-08-17
Topics:
Gutsulyak, B. M.
Turov, A. V.
Petrovskii, R. S.
Kornilov, M. Yu.
When carbazole is heated with formaldehyde and acetone (or with methyl vinyl ketone) in the presence of mineral acid, 3-methylpyrido<3,2-j,k>carbazolium salts form.These react with p-dimethylaminobenzaldehyde, triethyl orthoformate, Michler's ketone, 1-ethylquinolinium iodide, or 1,3,3-trimethyl-2-formylmethyleneindolinium iodide to give the respective cyanine dyes.Deviations of the unsymmetrical dyes and Hueckel molecular orbital calculations show that the Brooker basicity of the pyrido<3,2,1-j,k>carbazolium series is lower than that of the 1-phenylquinolinium series.
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