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Synthesis of Methylcytisine 9-Thiocarboxamides

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Chemistry of Natural Compounds Aims and scope

9-Carboxamide derivatives of the quinolizidine alkaloid methylcytisine were synthesized. The synthetic pathway included nitration-reduction according to the literature that resulted in 9-amination of the 2-pyridone core of the starting alkaloid. The obtained 9-amino derivative was converted by CS2 in Py in the presence of dicyclohexylcarbodiimide (DCC) into the corresponding isothiocyanate. The synthesized 9-isothio derivative was reacted with primary and secondary amines. The yields of the obtained 9-thiocarboxamide methylcytisine derivatives were 80–98%. The structures of the synthesized compounds were established using elemental analyses and IR, PMR, 13C NMR, and 15N NMR spectroscopy.

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Acknowledgment

The work was performed in the framework of a State Task for UfIC, UFRC, RAS, on topics Nos. AAAA-A17-117011910025-6 and AAAA-A17-117011910027-0.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 71 Prosp. Oktyabrya, Ufa, 450054, Russia

    P. R. Petrova, A. V. Koval’skaya, A. N. Lobov & I. P. Tsypysheva

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  1. P. R. Petrova
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  2. A. V. Koval’skaya
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  3. A. N. Lobov
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  4. I. P. Tsypysheva
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Correspondence to I. P. Tsypysheva.

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Petrova, P.R., Koval’skaya, A.V., Lobov, A.N. et al. Synthesis of Methylcytisine 9-Thiocarboxamides. Chem Nat Compd 55, 908–913 (2019). https://doi.org/10.1007/s10600-019-02843-z

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  • DOI: https://doi.org/10.1007/s10600-019-02843-z

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