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Paper | Regular issue | Vol 100, No. 4, 2020, pp.622-631
Published online, 4th March, 2020
DOI: 10.3987/COM-20-14235
Novel Ring Transformation of Uracils to 2-Oxazolidinones

Yoshiaki Kitamura,* Yuki Nagaya, Yuto Ohshima, Daiki Kato, Asuki Ohguchi, Hiroshi Katagiri, Masato Ikeda, and Yukio Kitade

*Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University , 1-1 Yanagido, Gifu, Gifu 501-1193, Japan

Abstract

Treatment of N3-electron-withdrawing group-protected uracil derivatives bearing a 2-hydroxyethyl moiety at the 1-position with base under anhydrous conditions affords the corresponding 2-oxazolidinone by opening the pyrimidine ring between C2 and N3, followed by ring closure between C2 and the neighbouring hydroxy group. This ring transformation is applicable to various uracil analogues to obtain the desired 2-oxazolidinone in moderate to excellent yield.