The synthesis of novel crown ethers, part IX, 3-phenyl chromenone-crown ethers

Bulut M., Erk C.

JOURNAL OF HETEROCYCLIC CHEMISTRY, cilt.38, sa.6, ss.1291-1295, 2001 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 38 Konu: 6
  • Basım Tarihi: 2001
  • Doi Numarası: 10.1002/jhet.5570380608
  • Sayfa Sayıları: ss.1291-1295


3-Phenyl- and 3-(p-methoxyphenyl)-7,8-dihydroxy and -6,7-dihydroxychromenones were prepared from ethyl 3-oxo-2-phenylpropanoate, ethyl 3-oxo-2-(4-methoxyphenyl)-propanoate and the trihydroxy benzenes in H2SO4. 3-Aryl-7,8- and 3-aryl-6,7-dihydroxy-2H-chromenones reacted with the bis-dihalides of polyglycols in DMF/MeCO3 to afford 12-Crown-4, 15-Crown-4 and 18-Crown-6-chromenones. The products were identified with IR, 1H NMR, low and high resolution mass spectroscopy and elemental analysis. Some 1: 1 cation association constants, K-b, of the 3-phenyl chromenone crown ethers with Li+, Na+, K+ and Rb+ cations were studied by steady state emission fluorescence spectroscopy; K-b chromenone-crown complexes displayed crown ether-cation binding selectivity rules properly in acetonitrile.