5-Amino-2,3-dihydro-1,2,4-oxadiazol-3-one 2 was synthesized as an analogue of cytosine. Among the possible four tautomers it was established by spectroscopic methods and ab initio calculations that it exists as a lactam form 2b like cytosine. The NH is more acidic than NH2, thus it could be regioselectively mesylated and acetylated under basic conditions.
D. Young Ra, N. Sook Cho, S. Kwon Kang, E. Suk Choi and I. Hwan Suh, J. Chem. Soc., Perkin Trans. 2, 1999, 81 DOI: 10.1039/A806491A
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