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Synthesis of 3-methylpyrido[3,2,1-j,k]carbazolium salts and derived cyanine dyes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

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 Hückel 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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Authors and Affiliations

  1. Ivano-Frankovsk Oil and Gas Institute, 284018, Ivano-Frankovsk

    B. M. Gutsulyak, A. V. Turov, R. S. Petrovskii & M. Yu. Kornilov

  2. T. G. Shevchenko State University, 252015, Kiev

    B. M. Gutsulyak, A. V. Turov, R. S. Petrovskii & M. Yu. Kornilov

Authors
  1. B. M. Gutsulyak
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  2. A. V. Turov
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  3. R. S. Petrovskii
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  4. M. Yu. Kornilov
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1059–1062, August, 1987.

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Gutsulyak, B.M., Turov, A.V., Petrovskii, R.S. et al. Synthesis of 3-methylpyrido[3,2,1-j,k]carbazolium salts and derived cyanine dyes. Chem Heterocycl Compd 23, 846–849 (1987). https://doi.org/10.1007/BF00473454

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  • DOI: https://doi.org/10.1007/BF00473454

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