Abstract
Methods for the preparation of three cyclic 2,3,4-tris(hydroxymethyl)-6-methylpyridin-5-ol acetonides have been developed by variation of the reaction conditions. The six-membered acetonide turned out to be thermodynamically more stable than the seven-membered acetonide and bis-acetonide. The experimental data were consistent with the results of quantum-chemical calculations. The structure of the isolated compounds was proved by X-ray analysis.
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Original Russian Text © N.V. Shtyrlin, O.A. Lodochnikova, M.V. Pugachev, T.I. Madzhidov, L.P. Sysoeva, I.A. Litvinov, E.N. Klimovitskii, Yu.G. Shtyrlin, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 4, pp. 569–575.
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Shtyrlin, N.V., Lodochnikova, O.A., Pugachev, M.V. et al. Theoretical and experimental study on cyclic 6-methyl-2,3,4-tris(hydroxymethyl)pyridin-5-ol acetonides. Russ J Org Chem 46, 561–567 (2010). https://doi.org/10.1134/S1070428010040202
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DOI: https://doi.org/10.1134/S1070428010040202