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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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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.

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Authors and Affiliations

  1. Southern Federal University, 7 Zorge St, Rostov-on-Don, 344090, Russia

    Anna V. Tkachuk, Sergey V. Kurbatov, Pavel G. Morozov & Gennadiy S. Borodkin

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  1. Anna V. Tkachuk
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  2. Sergey V. Kurbatov
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  3. Pavel G. Morozov
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  4. Gennadiy S. Borodkin
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Correspondence to Anna V. Tkachuk.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 948–950

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Tkachuk, A.V., Kurbatov, S.V., Morozov, P.G. et al. The first dipolar spirocycle based on 10-(benzylamino)colchicine. Chem Heterocycl Comp 51, 948–950 (2015). https://doi.org/10.1007/s10593-015-1803-5

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  • DOI: https://doi.org/10.1007/s10593-015-1803-5

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