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New Structural Modifications of Cotarnine Alkaloid Derivatives: Cotarnone and Dihydrocotarnine

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Abstract

Simplest derivatives of the cotarnine alkaloid, like cotarnone and 1,2-dihydrocotarnine, undergo electrophilic Einhorn acylamidomethylation (with 60–95% yield) and sulfochlorination with chlorosulfonic acid at position 5. At the same time cotarnone and its derivatives undergo additional O-protodemethylation. Using these and some other reactions, we synthesized a number of previously unknown derivatives of two substrates with 5-chloroacetamidomethyl, 5-arylaminomethyl, 5-aminomethyl and 5-sulfamide groups.

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Notes

  1. 1 Hereinafter, the numbers with a dash denote the protons of the aryl substituent.

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Authors and Affiliations

  1. InterBioScreen Ltd, 142432, Chernogolovka, Russia

    V. G. Kartsev

  2. North Caucasian Zonal Veterinary Research Institute, Federal Rostov Agrarian Scientific Center, 346406, Novocherkassk, Russia

    A. A. Zubenko

  3. Institute of Physical and Organic Chemistry of Southern Federal University, 344090, Rostov-on-Don, Russia

    L. N. Divaeva & A. S. Morkovnik

  4. N.D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences, 119991, Moscow, Russia

    T. K. Baryshnikova & V. Z. Shirinian

Authors
  1. V. G. Kartsev
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  2. A. A. Zubenko
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  3. L. N. Divaeva
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  4. A. S. Morkovnik
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  5. T. K. Baryshnikova
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  6. V. Z. Shirinian
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Correspondence to L. N. Divaeva.

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Kartsev, V.G., Zubenko, A.A., Divaeva, L.N. et al. New Structural Modifications of Cotarnine Alkaloid Derivatives: Cotarnone and Dihydrocotarnine. Russ J Gen Chem 90, 238–243 (2020). https://doi.org/10.1134/S1070363220020127

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  • DOI: https://doi.org/10.1134/S1070363220020127

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