Synthesis of 5(6H)-phenanthridones using Diels-Alder reaction of 3-nitro-2(1H)-quinolones acting as dienophiles.
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.
Fujita
Reiko
R
Tohoku Pharmaceutical University, Sendai, Japan. refujita@tohoku-pharm.ac.jp
Yoshisuji
Toshiteru
T
Wakayanagi
Sota
S
Wakamatsu
Hideaki
H
Matsuzaki
Hisao
H
D002070:Butadienes; D002855:Chromatography, Thin Layer; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D009574:Nitro Compounds / Q000138:chemical synthesis*; D010617:Phenanthridines / Q000138:chemical synthesis*; D015363:Quinolones / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared
D002070:Butadienes; D007202:Indicators and Reagents; D009574:Nitro Compounds; D010617:Phenanthridines; D015363:Quinolones; C031763:1,3-butadiene