Diels-Alder Reaction of 1, 3-Butadiene Derivatives with 1-Methyl-2(1H)-quinolones Having an Electron-Withdrawing Group at the 4-Position

Reiko FUJITA; Kazuhiro WATANABE; Toshiteru YOSHISUJI; Hiroshi HONGO; Hisao MATSUZAKI

doi:10.1248/cpb.49.900

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Diels-Alder Reaction of 1, 3-Butadiene Derivatives with 1-Methyl-2(1H)-quinolones Having an Electron-Withdrawing Group at the 4-Position

Reiko FUJITA, Kazuhiro WATANABE, Toshiteru YOSHISUJI, Hiroshi HONGO, Hisao MATSUZAKI

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Keywords: 1-methyl-2(1H)-quinolone, phenanthridone, isoprene, butadiene sulfone, electron-withdrawing group, MO calculation

JOURNAL FREE ACCESS

2001 Volume 49 Issue 7 Pages 900-904

DOI https://doi.org/10.1248/cpb.49.900

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Abstract

Diels-Alder reactions of 1-methyl-2(1H)-quinolones having an electron-withdrawing group at the 4-position with isoprene, butadiene sulfone, and cyclohexadiene were performed to yield functionalized phenanthridones stereoselectively at atmospheric and at high pressure. Regioselectivity and stereochemistry of a methoxycarbonyl group were studied using the semi-empirical and ab initio MO methods, respectively.

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