The chemistry of 4-azido-2-pyrimidinone nucleosides revisited.
Treatment of 4-azido-2-pyrimidinone nucleoside 1 with MeOH/K2CO3 or ammonium hydroxide led to derivatives 2 and 3, respectively. Both compounds derived from a nucleophilic addition at the modified base 2-position. These results contrast with the previously reported sensitivity of the 4-azido-2-pyrimidinone nucleoside 6-position to nucleophiles.
Peyrane
Frédéric
F
Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif-sur-Yvette, France.
Clivio
Pascale
P
D001386:Azides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000706:statistics & numerical data; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D011744:Pyrimidinones / Q000737:chemistry*
D001386:Azides; D009705:Nucleosides; D011744:Pyrimidinones