Abstract
Synthetic approaches to three cyclic 2,4,5,6-tetrakis(hydroxymethyl)pyridin-3-ol acetonides were developed. Among seven possible mono- and diketals, six-membered cyclic ketal incorporating the hydroxymethyl group in the 4-position turned out to be the most thermodynamically favorable. The experimental data were consistent with the results of quantum-chemical calculations of the Gibbs energies of formation of different acetonides. The structure of the isolated compounds was studied by X-ray diffraction.
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Original Russian Text © N.V. Shtyrlin, A.B. Dobrynin, T.I. Madzhidov, M.V. Pugachev, L.P. Sysoeva, R.Z. Musin, I.A. Litvinov, E.N. Klimovitskii, Yu.G. Shtyrlin, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 1, pp. 101–109.
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Shtyrlin, N.V., Dobrynin, A.B., Madzhidov, T.I. et al. Experimental and theoretical study on 6-substituted pyridoxine derivatives. Synthesis of cyclic 2,4,5,6-tetrakis-(hydroxymethyl)pyridin-3-ol acetonides. Russ J Org Chem 47, 100–108 (2011). https://doi.org/10.1134/S107042801101012X
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DOI: https://doi.org/10.1134/S107042801101012X