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Chemistry of Natural Compounds

, Volume 55, Issue 6, pp 1101–1105 | Cite as

Iodination of Cytisine and Methylcytisine Alkaloids

  • A. V. Koval’skaya
  • P. R. Petrova
  • A. N. Lobov
  • I. P. TsypyshevaEmail author
Article
  • 24 Downloads

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.

Keywords

quinolizidine alkaloids (–)-cytisine methylcytisine 2-pyridone core iodination 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • A. V. Koval’skaya
    • 1
  • P. R. Petrova
    • 1
  • A. N. Lobov
    • 1
  • I. P. Tsypysheva
    • 1
    Email author
  1. 1.Ufa Institute of Chemistry, Ufa Federal Research CenterRussian Academy of SciencesUfaRussia

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