Studies of Purine <i>N</i>-Oxides. II. The Reaction of Hypoxanthine 1-<i>N</i>-Oxide and 2′,3′,5′-Tri-<i>O</i>-acetylinosine 1-<i>N</i>-Oxide with Phosphoryl Chloride

Abstract

Abstract Hypoxanthine 1-N-oxide was treated with phosphoryl chloride in the presence of organic bases to give 2,6-dichloropurine. Adenosine 1-N-oxide was converted to inosine 1-N-oxide by deamination with nitrous acid. Inosine 1-N-oxide was acetylated with acetic anhydride in pyridine to yield 2′,3′,5′-tri-O-acetylinosine 1-N-oxide. The latter compound was similarly converted to 9-(2′,3′,5′-tri-O-acetyl-β-d-ribofuranosyl)-2,6-dichloropurine by treating it with phosphoryl chloride in the presence of organic bases.