Synthesis of 5(6H)-Phenanthridones Using Diels–Alder Reaction of 3-Nitro-2(1H)-quinolones Acting as Dienophiles

Reiko Fujita; Toshiteru Yoshisuji; Sota Wakayanagi; Hideaki Wakamatsu; Hisao Matsuzaki

doi:10.1248/cpb.54.204

Regular Articles

Synthesis of 5(6H)-Phenanthridones Using Diels–Alder Reaction of 3-Nitro-2(1H)-quinolones Acting as Dienophiles

Reiko Fujita, Toshiteru Yoshisuji, Sota Wakayanagi, Hideaki Wakamatsu, Hisao Matsuzaki

Author information

Keywords: 3-nitro-2(1H)-quinolone, Diels–Alder reaction, 6(5H)-phenanthridone, 1-methoxy-1,3-butadiene, 2,3-dimethoxy-1,3-butadiene, molecular orbital (MO) calculation

JOURNAL FREE ACCESS

2006 Volume 54 Issue 2 Pages 204-208

DOI https://doi.org/10.1248/cpb.54.204

Details

Abstract

Diels–Alder reactions of 3-nitro-2(1H)-quinolones with 1,3-butadiene derivatives were carried out to give the phenanthridone derivatives under both atmospheric and high pressure conditions. Furthermore, the reactivity of 3-substituted 2(1H)-quinolones acting as a dienophile with 2,3-dimethyl-1,3-butadiene was examined using molecular orbital (MO) calculation.

Corresponding author

Register with J-STAGE for free!