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Chemistry of Natural Compounds

, Volume 54, Issue 4, pp 739–744 | Cite as

Chemical Modification of Plant Alkaloids. 8. Stereocontrolled T-Reactions of (1R,5S,12S)-Tetrahydrocytisine Derivatives

  • K. A. KrasnovEmail author
  • V. G. Kartsev
  • E. V. Dobrokhotova
  • E. K. Kultyshkina
  • N. Yu. Chernikova
  • P. V. Dorovatovskii
  • Ya. V. Zubavichus
  • V. N. Khrustalev
Article
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New heterocyclic quinolizidine systems were prepared from (1R,5S,12S)-tetrahydrocytisine. The synthetic scheme included arylation of tetrahydrocytisine by 2-fluoro-5-nitrobenzaldehyde and condensation of the resulting aldehyde with 1,3-dimethylbarbituric acid. The Knoevenagel intermediate obtained from the condensation was cyclized by a T-reaction to give two spirocyclic products as a derivative with the lupanine skeleton and its regioisomer with the 11,15-diazapentacyclo[11.7.1.02,11.05,10.015,20]heneicosane skeleton. The cyclization occurred highly stereoselectively. The structures of the products were proven using NMR and X-ray crystal structure analyses.

Keywords

(1R,5S,12S)-tetrahydrocytisine 1,3-dimethylbarbituric acid hydride shift T-reaction lupanine derivative stereocontrolled synthesis 

Notes

Acknowledgment

We thank the Russian Foundation for Basic Research (Grant RFBR No. 16-29-10782-ofi_m) and PFUR Program 5-100 for financial support. X-ray measurements were made using the unique science facility at the Kurchatov synchrotron light source and were sponsored by the Ministry of Education and Science of the RF (Project Identifier RFMEFI61917X007).

References

  1. 1.
    K. Saito, S. Takamatsu, M. Yamazaki, S. Ohmiya, and I. Murakoshi, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 32, 268 (1990); Chem. Abstr., 114, 203603 (1991).Google Scholar
  2. 2.
    F. Bohlmann, E. Winterfeldt, H. Overwien, and H. Pagel, Chem. Ber., 95, 944 (1962).CrossRefGoogle Scholar
  3. 3.
    J. Rouden, M.-C. Lasne, J. Blanchet, and J. Baudoux, Chem. Rev., 114 (1), 712 (2014).CrossRefPubMedGoogle Scholar
  4. 4.
    A. Yu. Platonova, T. V. Glukhareva, O. A. Zimovets, and Yu. Yu. Morzherin, Khim. Geterotsikl. Soedin., 3, 386 (2013).Google Scholar
  5. 5.
    K. A. Krasnov and V. G. Kartsev, Zh. Org. Khim., 41 (6), 920 (2005).Google Scholar
  6. 6.
    K. A. Krasnov and V. G. Karcev, in: The Chemistry and Biological Activity of Synthetic and Natural Compounds. Nitrogen-Containing Heterocycles, Vol. 1, V. G. Karcev (ed.), ISCPF Press, Moscow, 2006, p. 76.Google Scholar
  7. 7.
    K. A. Krasnov and V. G. Kartsev, Heterocycles, 71 (1), 19 (2007).CrossRefGoogle Scholar
  8. 8.
    C. Rabong, C. Hametner, K. Mereiter, V. G. Kartsev, and U. Jordis, Heterocycles, 75, 799 (2008).CrossRefGoogle Scholar
  9. 9.
    K. A. Krasnov and V. G. Kartsev, Chem. Nat. Compd., 46, 915 (2011).CrossRefGoogle Scholar
  10. 10.
    K. A. Krasnov, V. G. Kartsev, E. V. Dobrokhotova, E. K. Kultyshkina, T. V. Timofeeva, and V. N. Khrustalev, Chem. Nat. Compd., 53, 703 (2017).CrossRefGoogle Scholar
  11. 11.
    K. A. Krasnov, V. G. Kartsev, and V. N. Khrustalev, Izv. Akad. Nauk, Ser. Khim., 52 (3), 675 (2003).Google Scholar
  12. 12.
    T. G. G. Battye, L. Kontogiannis, O. Johnson, H. R. Powell, and A. G. W. Leslie, Acta Crystallogr., Sect. D: Biol. Crystallogr., 67, 271 (2011).Google Scholar
  13. 13.
    P. Evans, Acta Crystallogr., Sect. D: Biol. Crystallogr., 62, 72 (2006).Google Scholar
  14. 14.
    G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem., 71, 3 (2015).Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • K. A. Krasnov
    • 1
    Email author
  • V. G. Kartsev
    • 2
  • E. V. Dobrokhotova
    • 3
  • E. K. Kultyshkina
    • 3
  • N. Yu. Chernikova
    • 3
  • P. V. Dorovatovskii
    • 4
  • Ya. V. Zubavichus
    • 4
  • V. N. Khrustalev
    • 3
    • 4
  1. 1.Institute of ToxicologyFederal Medico-Biological Agency of RussiaSt. PetersburgRussia
  2. 2.Interbioscreen Ltd.ChernogolovkaRussia
  3. 3.People’s Friendship University of RussiaMoscowRussia
  4. 4.National Research Center Kurchatov InstituteMoscowRussia

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