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■ Short-Step Synthesis of 1,3-Disubstituted Naphtho[2,3-c]furan-4,9-dione and Naphtho[2,3-b]furan-4,9-dione by the Friedel-Crafts Reaction

Junko Koyama,* Izumi Toyokuni, Akari Kino, and Kiyoshi Tagahara

*Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan

Abstract

1,3-Dialkylnaphtho[2,3-c]furan-4,9-diones were obtained by the Friedel-Crafts reaction of phthalic anhydride with 2,5-dialkylfurans. The reaction of phthalic anhydride with 2-acetyl-5-methylfuran, instead of 2,5-dialkylfurans, produced 2-methylnaphtho[2,3-b]furan-4,9-dione. The application of this method to the snthesis of 8-hydroxynaphtho[2,3-b]furan-4,9-dione [isodiodantunezone] is also described.