Experimental and theoretical study on 6-substituted pyridoxine derivatives. Synthesis of Cyclic 2,4,5,6-Tetrakis-(hydroxymethyl)pyridin-3-ol Acetonides

Abstract

© Pleiades Publishing, Ltd., 2011. 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.