PHOTO FRIES REARRANGEMENTS OF 1-NAPHTHYL ESTERS IN THE SYNTHESIS OF 2-ACYLNAPHTHOQUINONES

Article abstract of DOI:10.1021/jo00315a028

The photo Fries rearrangements of esters of 1-naphthol and 5-methoxy-1-naphthol to the corresponding 1-hydroxy-2-acylnaphthalenes have been carried out.The best yield (70percent) was obtained by irradiating 5-methoxy-1-naphthyl acetate in ethyl acetate.By contrast the yield from 1-naphthyl acetate under similar conditions was 40percent.Oxidation of 1-hydroxy-5-methoxy-2-naphthyl cyclohexyl ketone with thallium trinitrate gave the corresponding 1,4-quinone.These results provide a method for the regioselective synthesis of tricyclic analogues of adriamycinone.