Oxidative rearrangements of alkyl substituted isoquinoline enamides to 1-hydroxymethyldihydroisoquinoline derivatives

Oxidation of disubstituted 1 -methylenedihydroisoquinoline enamides with lead tetraacetate results in a novel N-->C oxidative rearrangement whereby esters of disubstituted 1-hydroxymethyl-3,4-dihydroisoquinoline are formed. An X-ray crystallographic structural determination for 6,7-dimethoxy-1-[1-(p-methoxybenzoyloxy)-1-methylethyl]-3,4-dihydroisoquinoline 4 is described.