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Chemistry of Heterocyclic Compounds

, Volume 51, Issue 10, pp 948–950 | Cite as

The first dipolar spirocycle based on 10-(benzylamino)colchicine

  • Anna V. TkachukEmail author
  • Sergey V. Kurbatov
  • Pavel G. Morozov
  • Gennadiy S. Borodkin
Article

We have synthesized the first dipolar spirocyclic σ-complex of Meisenheimer type from 10-(benzylamino)colchicine and trinitrobenzene. The chirality of colchicine moiety resulted in magnetic non-equivalence of protons in the trinitrophenyl ring, enabling their use as diastereotopic markers. The kinetic and activation parameters for the reversible degenerate recyclization of spirocycle were determined by a dynamic NMR method.

Keywords

colchicine dipolar spirocycle nucleophilic aromatic substitution stereodynamics 

Notes

This work was performed within the framework of Project part of the State Assignment for scientific activity No. 4.129.2014/K from Ministry of Education and Science of the Russian Federation.

Supplementary material

10593_2015_1803_MOESM1_ESM.pdf (1.6 mb)
Supplementary information file (PDF 1590 kb)

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Anna V. Tkachuk
    • 1
    Email author
  • Sergey V. Kurbatov
    • 1
  • Pavel G. Morozov
    • 1
  • Gennadiy S. Borodkin
    • 1
  1. 1.Southern Federal UniversityRostov-on-DonRussia

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