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Communication | Special issue | Vol 8, No. 1, 1977, pp.257-262
Published online, 1st January, 1970
DOI: 10.3987/S(S)-1977-01-0257
On the Structural Ditermination of Pyrimidine N-Oxides

Takao Sakamoto, Setsuko Niitusma, Michinao Mizugaki, and Hiroshi Yamanaka*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Direct N-oxidation of 2-alkyl-4-ethyl-6-methylpyrimidines with hydrogen peroxide in glacial acetic acid afforded their 1-oxides and 3-oxides. Acid hydrolysis of the 1-oxides and the 3-oxides caused the ring transformation leading to 3-methyl-5-ethyl- (VII) and 3-ethyl-5-methyl-isoxazole (VIII), respectively. This result obviously demonstrated the structure of the N-oxides.
Observing displacements of signals on the NMR spectra of the N-oxides induced by adding a shift reagent, tris(heptafluorobutanoylpivaloylmethanato)europiumIII), it is concluded that the NMR spectroscopy with the lanthanide is generally applicable to structural elucidation of pyrimidine N-oxides.