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Communication | Regular issue | Vol 16, No. 4, 1981, pp.573-576
Published online, 1st January, 1970
DOI: 10.3987/R-1981-04-0573
Oxidation of 2,4-Disubstituted Pyrimidines with Organic Peracids

Hiroshi Yamanaka,* Shigeru Ogawa, and Takao Sakamoto

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

Abstract

While 4,6-disubstituted (alkyl, aryl, alkoxyl) pyrimidines easily afforded the corresponding mono-N-oxides with hydrogen peroxide in glacial acetic acid, pyrimidine derivatives whose 6-position is free, are partly oxidatively degradated during N-oxidation reaction. The oxidation of the latter compounds under the above conditions gave 2,4-disubstituted imidazoles together with their mono-N-oxides. A likely mechanism of this ring-contraction and the improved conditions for the synthesis of the N-oxides are also described.