Phenol oxidation and biosynthesis. Part 26. Isonitriles in the synthesis of benzylisoquinoline derivatives

Abstract

Lithiomethyl and toluene-4-sulphonyl(potassiomethyl)isonitriles have been applied in short high-yield homologations of O-benzylvanillin, O-benzylisovanillin, and veratraldehyde giving N-(2-arylethyl)-2-arylacetamides and subsequently isoquinoline derivatives. These experiments are relevant to the preparation of alkaloids including papaverine and reticuline.