Synthesis of Phenanthridones Using Diels—Alder Reactions of 4-Substituted 2(1H)-Quinolones Acting as Dienophiles

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

doi:10.1248/cpb.49.407

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Synthesis of Phenanthridones Using Diels—Alder Reactions of 4-Substituted 2(1H)-Quinolones Acting as Dienophiles

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

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Keywords: 4-substituted 2(1H)-quinolone, Diels-Alder reaction, phenanthridone, MO calculation, high pressure, electron-withdrawing group

JOURNAL FREE ACCESS

2001 Volume 49 Issue 4 Pages 407-412

DOI https://doi.org/10.1248/cpb.49.407

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Abstract

Diels—Alder reactions of 2(1H)-quinolones having an electron-withdrawing group at the 4-position with 1, 3-butadiene derivatives were carried out to give the phenanthridones richly functionalized under the conditions of atmospheric and high pressure. Furthermore, the reactivities of 4-substituted 2(1H)-quinolones acting as a dienophile were examined using MO calculation.

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