New beta-tricarbonyl compounds: Synthesis, reactions with urea and some thioureas

Sacmaci M., Alkan A., SAÇMACI Ş., SARIPINAR E., ŞAHİN E.

HETEROCYCLES, vol.75, no.8, pp.2013-2021, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 75 Issue: 8
  • Publication Date: 2008
  • Doi Number: 10.3987/com-08-11357
  • Journal Name: HETEROCYCLES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2013-2021
  • Keywords: furan-2,3-dione, beta-tricarbonyl, pyrimidine, oxazine, X-ray, CYCLIC OXALYL COMPOUNDS, CHEMICAL-REACTIVITY, DIFFRACTION, DERIVATIVES
  • Erciyes University Affiliated: Yes

Abstract

2,3-Dihydro-4-(4-methoxybenzoyl)-5-(4-methoxyphenyl)furan-2,3-dione 1 reacted with some alkyl carbamates (3a-b) via p,p'-dimethoxy-dibenzoylketene intermediate 2 giving new beta-tricarbonyl compounds (4a-b). Then, these compounds were converted into 1,3-oxazine-2,4(3H)-dione 7 with urea and 2-thioxo-2,3-dihydropyrimidin-4(1H)-ones (6a-c) with some thiourea derivatives, respectively. Pyrimidin-4-ones (6a-c) and oxazine 7 were obtained in good yields. The structures and characterizations of new synthesized compounds were established by the H-1 and C-13 NMR, IR, UV-VIS spectroscopic data, elemental analysis, and X-ray diffraction method.