Synthesis of 7,8-Dihydroxy-3-(3,4-dihydroxyphenyl)-2H-chromen-2-one Derivatives of Crown Ethers

Gunduz C., Bulut M.

JOURNAL OF HETEROCYCLIC CHEMISTRY, cilt.46, sa.1, ss.105-107, 2009 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 46 Sayı: 1
  • Basım Tarihi: 2009
  • Doi Numarası: 10.1002/jhet.17
  • Dergi Adı: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.105-107
  • Marmara Üniversitesi Adresli: Evet

Özet

The novel 1-(3,4-dimethoxyphenyl)-2-(2,3,4-trimethoxyphenyl)acrylonitrile was prepared from the condensation of the mixture of 2,3,4-trimethoxybenzaldehyde and 3,4-dimethoxyphenylacetonitrile in ethanol at 70 degrees C with 20% aqueous sodium hydroxide solution. Cyclization and demethylation of the acrylacetonitrile was performed using pyridine hydrochloride. The obtained 7,8-dihydroxy-3-(3,4-dihydroxyphenyl)-2H-chromen-2-one was reacted with the poly(ethylene glycol) ditosylates in CH3CN/alkali carbonate to afford bis-[12]crown-4, -[15]crown-5, and -[18]crown-6 chromenones. The chromatographically purified novel chromenone crown ethers were identified by IR, H-1 NMR, C-13 NMR, and MALDI-TOF mass spectrometry and elemental analysis.