The Chemistry of Phthalide-3-carboxylic Acid. V. The Reaction of the Acid With Imines
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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 130�, the product is the 3-alkyl 3-hydroxyisoindolone or its dehydration product, but in acetic anhydride at 130� 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.Keywords:
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