A study on chemical behaviors of some 4-pyrones synthesized by one-step reactions towards various amines


ŞENER A., ESKINOBA S., Bildirici I. , Genc H. , KASIMOGULLARI R.

JOURNAL OF HETEROCYCLIC CHEMISTRY, cilt.44, ss.337-341, 2007 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 44 Konu: 2
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1002/jhet.5570440209
  • Dergi Adı: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Sayfa Sayıları: ss.337-341

Özet

Cycloaddition of acetylbenzoyl ketene generated in situ as an intermediate during one-step reaction between excess benzoylacetone and oxalylchloride to C=C double bond of cyclic enol form of benzoylacetone gave 3-acetyl-5-benzoyl-6-methyl-2-phenyl-4(4H)-pyrone 1a. Condensation reactions of la together with 3,5-dibenzoyl-2,6-diphenyl-4(4H)-pyrone 1b and 3-benzoyl-5-ethoxycarbonyl-2,6-diphenyl-4(4H)-pyrone 1c with two-fold excess primary amines provided a series of 3-benzoyl-1-alkyl-5-(1-alkylimino-ethyl)-6-phenyl-2-methyl-4(1H)-pyridinone 2, 3,5-dibenzoyl-1-alkyl-2,6-diphenyl-4(1H)pyridinone 3a-c and 3-benzoyl-1-alkyl-5-ethoxycarbonyl-2,6-diphenyl-4(1H)-pyridinone 3d,e derivatives, respectively. In addition, while prolonged reaction of n-pentylamine with unsymmetrical pyrone derivative la gives a symmetrical pyridinone derivative namely 3,5-dibenzoyl-2,6-dimethyl-1-pentyl-4(1H)pyridinone 5, much prolonged action n-pentylamine and then aqueous n-pentylamine on 1b resulted in degradation of the 4-pyrone ring to give dibenzoylmethane.