The Chemistry of Phthalide-3-carboxylic Acid. VI. The Stereochemistry of Some 3-Amino(aryl)methylphthalides and the Derived 3-Aryl-4-hydroxy-3,4-dihydroisoquinolin-1(2H)-ones

Abstract

The isomeric 3-[hydroxy(phenyl)methyl]isobenzofuran-1(3H)-ones, of known configuration, have been converted into the corresponding amino and dimethylamino compounds with inversion of configuration, and hence the stereochemistry of these compounds has been determined. The amino compounds have been converted into the corresponding 3-aryl-4-hydroxy-3,4-dihydroisoquinolin-l(2H)-ones, confirming their stereochemical assignments. Attempted displacement of the tosyloxy group in the isomeric 3- [phenyl(toluenesulfonyloxy)methyl]isobenzofuran-l(3H)-ones with dimethylamine proceeded by rearrangement to an epoxy amide and a keto amide.