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Russian Journal of Organic Chemistry

, Volume 47, Issue 1, pp 100–108 | Cite as

Experimental and theoretical study on 6-substituted pyridoxine derivatives. Synthesis of cyclic 2,4,5,6-tetrakis-(hydroxymethyl)pyridin-3-ol acetonides

  • 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
Article

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.

Keywords

Acetic Anhydride Hydroxymethyl Group Sodium Ethoxide Column Chroma Hydrogen Bond Parameter 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • N. V. Shtyrlin
    • 1
  • A. B. Dobrynin
    • 2
  • T. I. Madzhidov
    • 1
  • M. V. Pugachev
    • 1
  • L. P. Sysoeva
    • 1
  • R. Z. Musin
    • 2
  • I. A. Litvinov
    • 2
  • E. N. Klimovitskii
    • 1
  • Yu. G. Shtyrlin
    • 1
  1. 1.Butlerov Institute of ChemistryKazan (Privolzhsk) Federal UniversityKazanTatarstan, Russia
  2. 2.Arbuzov Institute of Organic and Physical Chemistry, Kazan Research CenterRussian Academy of SciencesKazanTatarstan, Russia

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