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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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