Showing papers by "John Chiefari published in 1989"
TL;DR: In the presence of imines, phthalide-3-carboxylic acids decarboxylate readily in the presence or absence of imine, the product depending on the solvent used as mentioned in this paper, and in acetic anhydride at 130o the product is a mixture of diastereoisomeric 3-acetylarninoalkylphthalides.
Abstract: Phthalide-3-carboxylic acids decarboxylate readily in the presence of imines, the product depending on the solvent used. In dimethyl sulfoxide, or in the absence of solvent, at 130o, the product is the 3-alkyl 3-hydroxyisoindolone or its dehydration product, but in acetic anhydride at 130o the product is a mixture of diastereoisomeric 3-acetylarninoalkylphthalides. The reactions can be applied to the synthesis of natural products such as the isoindoloisoquinoline and phthalideisoquinoline alkaloids.
6 citations