Abstract
Reactions of two isomeric nitropyrimidinones with bidentate enolate anions were studied. When 3-methyl-5-nitropyrimidin-4(3H)-one (1) was employed, ring transformation proceeded to give pyridin-4(1H)-ones 3 functionalized at the 3- or 5-positions. This pyrimidin-4-one 1 behaved as an activated diformylamine HN(CHO)2. 1-Methyl-5-nitropyrimidin-2(1H)-one (2) afforded polyfunctionalized bicyclo[3.3.1]nonene derivatives 7 and 8 and/or p-nitrophenol derivatives 9. In this case, pyrimidin-2-one 2 acted as the synthetic equivalent of unstable O2NCH(CHO)2. These two nitropyrimidinones are valuable intermediates for the synthesis of polyfunctionalized compounds.
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