A simple synthesis of 5-ethoxycarbonyl-6-phenyl-1,3-dioxin-4-ones and ethyl 3-benzoyl-4-oxo-2,6-diphenylpyran-5-carboxylate

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SENER A., Genc H., SENER M.

JOURNAL OF HETEROCYCLIC CHEMISTRY, vol.40, no.4, pp.697-700, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 40 Issue: 4
  • Publication Date: 2003
  • Doi Number: 10.1002/jhet.5570400422
  • Journal Name: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.697-700
  • Van Yüzüncü Yıl University Affiliated: Yes

Abstract

4-Ethoxycarbonyl-5-phenyl-2,3-dihydrofuran-2,3-dione 1 reacts with aldehydes via the acylketene intermediate 2 giving the 1,3-dioxin-4-ones 3a-e and the 1,4-bis(5-ethoxycarbonyl-4-oxo-6-phenyl-4H-1,3-dioxin-2-yl)benzene 4, and a one step reaction between dibenzoylmethane and oxalylchloride gave 3,5-dibenzoyl-2,6-diphenyl-4-pyrone 7. The reaction of 1 with dibenzoylmethane, a dicarbonyl compound, provided ethyl 3-benzoyl-4-oxo-2,6-diphenylpyran-5-carboxylate derivative 9. Compound 9 was converted into the corresponding ethyl 3-benzoyl-4-hydroxy-2,6-diphenylpyridine-5-carboxylate derivative 10 via its reaction with ammonium hydroxyde solution in 1-butanol.