Oxidation and reduction of 5-hydroxy-2-methylnaphtho[1,2-b]furan

Abstract

5-Hydroxy-2-methylnaphtho[1,2-b]furan (I; R = H) was obtained by decarboxylation of its 3-carboxylic acid. Treated with a number of one-electron oxidants, it underwent attack ortho to the hydroxy-group, generally giving rise to the corresponding ortho-quinone (II) but in the case of lead tetra-acetate yielding the related gem-diacetate (III). Treated with sodium in ethanol, it was reduced in the unsubstituted benzenoid ring, forming the 6,9-dihydro-derivative (IV). Oxidation or reduction of the furan ring was not observed.