Synthesis of azanucleosides through regioselective ring-opening of epoxides catalyzed by sulphated zirconia under microwave and solvent-free conditions

Molecules. 2012 Mar 15;17(3):3359-69. doi: 10.3390/molecules17033359.

Abstract

New azanucleosides were obtained using sulphated zirconia (ZS) as catalyst in the nucleophilic oxirane ring opening reaction of 1-allyl-3-(oxiran-2-ylmethyl) pyrimidine-2,4(1H,3H)-dione and 1-allyl-5-methyl-3-(oxiran-2-ylmethyl)-pyrimidine-2,4(1H,3H)-dione, with (S)-prolinol. The new templates were obtained with good yields following a route which exploits the reactivity of epoxides in the presence of sulphated zirconia as catalyst. The key step was carried out using microwave and solvent-free conditions and proceeds with high selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Epoxy Compounds / chemistry*
  • Microwaves*
  • Molecular Structure
  • Nucleosides / chemistry*
  • Stereoisomerism
  • Zirconium / chemistry*

Substances

  • Epoxy Compounds
  • Nucleosides
  • Zirconium
  • zirconium oxide