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Communication | Regular issue | Vol 23, No. 5, 1985, pp.1085-1088
Published online, 1st January, 1970
DOI: 10.3987/R-1985-05-1085
■ Regioselective Synthesis of Substituted Phthalides via Intramolecular "Diene-regenerative" Diels-Alder Reaction of 2-Pyrones

Michihiko Noguchi,* Shinji Kakimoto, Hisao Kawakami, and Shoji Kajigaeshi

*Department of Applied Chemistry, Faculty of Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan

Abstract

Some 2-pyrone-6-carboxylates bearing appropriate dienophiles in ester moieties underwent “diene-regenerative” Diels-Alder reaction to afford the dihydrophthalides, which were aromatized to phthalide derivatives in the presence of palladium-charcoal. In these reactions the substituents at 4 or 7-position of phthalides arose from those on the dienophile moieties in the starting 2-pyrones.