Formation of 6-formyl-7-hydroxy-8-methoxycoumarin and 5,8-dioxopsoralen by reaction of 8-methoxypsoralen with H2O2 and potassium superoxide (KO2) catalyzed by halogenated or perhalogenated 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides

Chem Pharm Bull (Tokyo). 2001 Sep;49(9):1232-3. doi: 10.1248/cpb.49.1232.

Abstract

The oxidation of 8-methoxypsoralen (2) with hydrogen peroxide and potassium superoxide catalyzed by 5,10,15,20-(2,4,6-trimethylphenyl)porphyrinatoiron(III) chlorides [Me12TPPFe(III)Cl] (1a) and 5,10,15,20-(2,6-dichlorophenyl)porphyrinatoiron(III) chlorides [Cl8TPPFe(III)Cl] (1b) in dichloromethane gives 6-formyl-7-hydroxy-8-methoxycoumarin (3) in moderate yields, whereas the oxidation of (2) with H2O2 catalyzed by 5,10,15,20-(2,6-dichlorophenyl)-beta-octahaloporphyrinatoiron(III) chlorides [Cl8betaX8TPPFe(III)Cl] (X=Cl, Br) (1c, 1d) gives specifically 5,8-dioxopsoralen (4) in moderate yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Coumarins / chemical synthesis*
  • Hydrogen Peroxide / chemistry*
  • Magnetic Resonance Spectroscopy
  • Methoxsalen / chemical synthesis*
  • Oxidation-Reduction
  • Spectrometry, Mass, Electrospray Ionization
  • Superoxides / chemistry*

Substances

  • 6-formyl-7-hydroxy-8-methoxycoumarin
  • Coumarins
  • Superoxides
  • Hydrogen Peroxide
  • Methoxsalen