109329-08-0Relevant academic research and scientific papers
The Chemistry of Phthalide-3-carboxylic Acid. V The Reaction of the Acid with Imines
Chiefari, John,Janowski, Wit K.,Prager, Rolf H.
, p. 49 - 60 (2007/10/02)
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 deg, the product is the 3-alkyl 3-hydroxyisoindolone or its dehydration product, but in acetic anhydride at 130 deg the product is a mixture of diastereoisomeric 3-acetylaminoalkylphthalides.The reactions can be applied to the synthesis of natural products such as the isoindoloisoquinoline and phthalideisiquinoline alkaloids.
DECARBOXYLATION OF PHTHALIDECARBOXYLIC ACIDS IN THE PRESENCE OF IMINES - A FACILE ROUTE TO ISOINDOLOBENZAZEPIN-5-ONES AND PHTHALIDEISOQUINOLINES
Chiefari, John,Janowski, Wit,Prager, Rolf
, p. 6119 - 6122 (2007/10/02)
In aprotic solvents, or in the absence of any solvent, phthalidecarboxylic acids decarboxylate in the presence of imines at 130o to form 3-alkyl-3-hydroxyisoindolones or their dehydration products.In acetic anhydride as solvent the products obtained are acetylated aminoalkylphthalides.The reactions are used to synthesise isoindolobenzazepin-5-ones and phthalideisoquinoline alkaloids.
