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Note | Special issue | Vol 67, No. 2, 2006, pp.807-814
Published online, 28th October, 2005
DOI: 10.3987/COM-05-S(T)78
Novel Methods of Synthesizing Naphtho[1,2-c]furan-1,3-dione and Benzo[e]isoindole-1,3-dione

Masahiro Mizuno* and Mitsuhisa Yamano

*Chemical Development Laboratory, Takeda Chemical Industries, Ltd., 17-85 Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan

Abstract

Convenient methods of synthesizing naphtho[1,2-c]furan-1,3-dione and benzo[e]isoindole-1,3-dione from phenylbutyric acid derivatives have been established. Naphtho[1,2-c]furan-1,3-dione and benzo[e]isoindole-1,3-dione were obtained respectively from 4,5-dihydronaphtho[1,2-c]furan-1,3-dione and 4,5-dihydrobenzo[e]isoindole-1,3-dione by aromatization with 10% Pd-C in AcOH under mild conditions. In addition, benzo[e]isoindole-1,3-dione derivatives were obtained from 4,5-dihydronaphtho[1,2-c]furan-1,3-dione by imidation and simultaneous aromatization with primary amine in AcOH in one pot.