Iodination of the 2-pyridone core of (–)-cytisine and methylcytisine by one equivalent of ICl or N-iodosuccinimide (NIS) in acidic solution gave primarily the 9-iodo derivatives although the starting alkaloid was incompletely converted. Use of an excess of the reagents under the same conditions gave 9,11-diiodo derivatives in 72 and 76% yields. 9-Iodomethylcytisine was prepared (61% yield in two steps) by treatment of methylcytisine with an excess of NIS in trifluoroacetic acid followed by deiodination of the 9,11-diiodo derivative by Zn dust in a mixture of EtOH and aqueous HCl.
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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November−December, 2019, pp. 947−950.
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Koval’skaya, A.V., Petrova, P.R., Lobov, A.N. et al. Iodination of Cytisine and Methylcytisine Alkaloids. Chem Nat Compd 55, 1101–1105 (2019). https://doi.org/10.1007/s10600-019-02904-3
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DOI: https://doi.org/10.1007/s10600-019-02904-3