Chemistry of Pyrones, Part 5: New Crown Ether and Podand Derivatives of 3,5-Bis(bromomethyl)-2,6-diphenyl-4H-pyran-4-one

Abstract

New podand and crown ether derivatives of 3,5-disubstituted 4H-pyran-4-one (8-11) were prepared by the nucleophilic substitution reaction of 3,5-bis(bromomethyl)-2,6-diphenyl-4H-pyran-4-one with o-nitrophenol, 8-hydroxyquinoline, 2-hydroxymethyl pyridine and triethyleneglycol, respectively. The yield of 3,5-bis[(2-formylphenoxy) methyl]-2,6-diphenyl-4H-pyran-4-one has been improved by modification of our previous method using NaOH instead of Et3N.

Keywords

• Crown ether
• Podands
• 4H-pyran-4-one
• Open-chain crown
• Nucleophilic substitution