Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Pyrimidine Derivatives. XIV. On the Structural Determination of Pyrimidine N-Oxides
TAKAO SAKAMOTOSETSUKO NIITSUMAMICHINAO MIZUGAKIHIROSHI YAMANAKA
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1979 Volume 27 Issue 11 Pages 2653-2660

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Abstract
N-Oxidation of pyrimidines having unsymmetrically substituted 4-and 6-positions with hydrogen peroxide in acetic acid gave mixture of their 1-oxides and 3-oxides. Ring transformation of these 1-oxides and 3-oxides into isoxazoles occurred on treatment with mineral acid, and provided information on the position of the N-oxide group in the pyrimidine N-oxides. Nuclear magnetic resonance spectroscopy with a lanthanide shift reagent was also found to be useful in identifying the pyrimidine 1-and 3-oxides.
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