A new approach to the synthesis of 7, 8-dioxygenated tetrahydroisoquinoline alkaloids based on the phot-Fries rearrangement of esters derived from 3-hydroxy-4-methoxy phenylacetonitrile is reported. The procedure was applied to the synthesis of the alkaloid Arizonine and 1-benzyl tetrahydroisoquinoline precursor of cularine and 1, 2-berbine alkaloids.