PDF herunterladen
Synthesis 1997; 1997(11): 1277-1280
DOI: 10.1055/s-1997-1353
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

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