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THE FIRST DIPOLAR SPIROCYCLE BASED ON 10-(BENZYLAMINO)COLCHICINE

Анна В. Ткачук, Сергей В. Курбатов, Павел Г. Морозов, Геннадий С. Бородкин
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Abstract


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.

How to Cite
Tkachuk, A. V.; Kurbatov, S. V.; Morozov, P. G.; Borodkin, G. S. Chem. Heterocycl. Compd. 2015, 51, 948. [Khim. Geterotsikl. Soedin. 2015, 51, 948.]

For this article in the English edition see DOI 10.1007/s10593-015-1803-5

 


Keywords


colchicine; dipolar spirocycle; nucleophilic aromatic substitution; stereodynamics

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