Diels-Alder Cycloadditions of 2(1H)-Quinolones Having an Electron-Withdrowing Group at the 3-Position Acting as Dienophiles with Dienes

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

doi:10.1248/cpb.49.893

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Diels-Alder Cycloadditions of 2(1H)-Quinolones Having an Electron-Withdrowing Group at the 3-Position Acting as Dienophiles with Dienes

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

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Keywords: 3-substituted 2(1H)-quinolone, Diels-Alder cycloaddition, regioselectivity, chemoselectivity, electron-withdrawing group, MO calculation

JOURNAL FREE ACCESS

2001 Volume 49 Issue 7 Pages 893-899

DOI https://doi.org/10.1248/cpb.49.893

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Abstract

Diels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position with alkyl- and silyloxy-1, 3-butadienes (2a, b) were carried out to give phenanthridones richly functionalized regio- or stereoselectively under conditions of atmospheric and high pressure. Furthermore, regioselectivity and chemoselectivity of 3-substituted 2(1H)-quinolones to 2a, b were examined using MO calculation.

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