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Indolizines

IV. Protonation of 2-alkyl(aryl)-6- and -7-carbethoxyindolizines and their formyl, acetyl, and nitroso derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It was established by PMR spectroscopy that 2-alkyl(aryl)-6- and -7-carbethoxyindolizines are protonated at C3, whereas their 3-formyl, 3-acetyl, and 3-nitroso derivatives are protonated at the oxygen atom of the substituent in the 3 position. The ionization constants of 24 indolizine derivatives in nitromethane relative to diphenylguanidine were measured by potentiometric titration. A correlation between protonation and electrophilic substitution in the 2-alkyl(aryl)-6- and -7-carbethoxyindolizine series was established.

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Literature cited

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Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical-Chemistry Institute, Moscow

    L. M. Alekseeva, G. G. Dvoryantseva, M. S. Goizman, T. S. Loseva, A. D. Yanina, E. E. Mikhlina, Yu. N. Sheinker & L. N. Yakhontov

Authors
  1. L. M. Alekseeva
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  2. G. G. Dvoryantseva
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  3. M. S. Goizman
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  4. T. S. Loseva
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  5. A. D. Yanina
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  6. E. E. Mikhlina
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  7. Yu. N. Sheinker
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  8. L. N. Yakhontov
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Additional information

See [1] for communication III.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1540–1545, November, 1976.

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Alekseeva, L.M., Dvoryantseva, G.G., Goizman, M.S. et al. Indolizines. Chem Heterocycl Compd 12, 1267–1272 (1976). https://doi.org/10.1007/BF00470229

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  • DOI: https://doi.org/10.1007/BF00470229

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