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Ipso-Substitution in Derivatives of the Quinoline Alkaloid Skimmianine

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Chemistry of Natural Compounds Aims and scope

Oxidation of the alkaloid skimmianine produced a formyl derivative that reacted with homoveratrylamine to give the product of nucleophilic ipso-substitution 3-formyl-4-(3,4-dimethoxyphenylethylamino)-7,8- dimethoxyquinolin-2-one. The presence of the formyl group in the latter stimulated its further ipso-substitution at the H atom in acidic solution to form 4-(3,4-dimethoxyphenylethylamino)-7,8-dimethoxyquinolin-2-one, the structure of which was confirmed by an X-ray crystal structure analysis.

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Acknowledgment

The work was financially supported by the Ministry of Innovative Development of the Cabinet of Ministers of the Republic of Uzbekistan (Grant MRU-FA-21/2017).

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Authors and Affiliations

  1. S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, Uzbekistan

    M. A. Eshonov, V. I. Vinogradova, Kh. A. Rasulova, K. K. Turgunov & B. Tashkhodzhaev

  2. Turin Polytechnic University, Tashkent, Uzbekistan, 100095

    K. K. Turgunov

Authors
  1. M. A. Eshonov
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  2. V. I. Vinogradova
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  3. Kh. A. Rasulova
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  4. K. K. Turgunov
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  5. B. Tashkhodzhaev
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Correspondence to M. A. Eshonov.

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Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2021, pp. 432–436.

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Eshonov, M.A., Vinogradova, V.I., Rasulova, K.A. et al. Ipso-Substitution in Derivatives of the Quinoline Alkaloid Skimmianine. Chem Nat Compd 57, 507–511 (2021). https://doi.org/10.1007/s10600-021-03398-8

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  • DOI: https://doi.org/10.1007/s10600-021-03398-8

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