Experimental and theoretical study on 6-substituted pyridoxine derivatives. Synthesis of cyclic 2,4,5,6-tetrakis-(hydroxymethyl)pyridin-3-ol acetonides |
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| Authors: | 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 |
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| Affiliation: | 1. Butlerov Institute of Chemistry, Kazan (Privolzhsk) Federal University, ul. Kremlevskaya 18, Kazan, 420008, Tatarstan, Russia
2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia
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| 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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