Nitropyrimidinones; Synthetic Equivalents of Diformylamine and Nitromalonaldehyde

Nagatoshi Nishiwaki; Yasuo Tohda; Masahiro Ariga

doi:10.1055/s-1997-1353

Synthesis 1997; 1997(11): 1277-1280
DOI: 10.1055/s-1997-1353

paper

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Nitropyrimidinones; Synthetic Equivalents of Diformylamine and Nitromalonaldehyde

Nagatoshi Nishiwaki¹ , Yasuo Tohda¹ , Masahiro Ariga²

¹Department of Chemistry, Osaka Kyoiku University, Asahigaoka 4-698-1, Kashiwara, Osaka 582, Japan
²Department of Chemistry, Osaka Kyoiku University, Asahigaoka 4-698-1, Kashiwara, Osaka 582, Japan, Fax +81(792)783399; E-mail: arigo@cc.osaka-kyoiku.ac.jp

Abstract

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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.

nitropyrimidinone - activated diformylamine - nitromalonaldehyde - ring transformation - functionalized pyridone

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