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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 12, pp 1131–1138 | Cite as

Synthesis of hybrid molecules containing pyrimidine and diterpene alkaloid lappaconitine fragments

  • Kirill P. Cheremnykh
  • Viktor А. Savel’ev
  • Oleg P. Shkurko
  • Elvira E. ShultsEmail author
Article
  • 16 Downloads

The cross coupling of 5'-ethynyllappaconitine with benzoic acid chlorides under the conditions of the Sonogashira reaction in benzene leads to the corresponding 5-alkynones. By condensation of the obtained 5'-alkynones with amidines, compounds with hybrid structure containing fragments of a diterpene alkaloid and pyrimidine were synthesized. The yields of the target compounds were 67–90%. The possibility of carrying out the cross coupling – condensation reaction as a one-pot synthesis is demonstrated.

Keywords

alkaloids alkynes amidines pyrimidines cross coupling one-pot synthesis 

Notes

This work was supported by the Russian Science Foundation (project No. 18-13-00361).

Analytical and spectral studies were performed at the Chemical Research Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.

Supplementary material

10593_2019_2404_MOESM1_ESM.pdf (1.2 mb)
ESM 1 (PDF 1222 kb)

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Copyright information

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

Authors and Affiliations

  • Kirill P. Cheremnykh
    • 1
  • Viktor А. Savel’ev
    • 1
  • Oleg P. Shkurko
    • 1
  • Elvira E. Shults
    • 1
    • 2
    Email author
  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic ChemistrySiberian Branch of the Russian Academy of SciencesNovosibirskRussia
  2. 2.Novosibirsk State UniversityNovosibirskRussia

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