Diels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position acting as dienophiles with dienes.
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.
Fujita
R
R
Tohoku Pharmaceutical University, Sendai, Japan. refujita@tohoku-pharm.ac.jp
Watanabe
K
K
Yoshisuji
T
T
Kabuto
C
C
Matsuzaki
H
H
Hongo
H
H
D003500:Cyclization; D004583:Electrons; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D015363:Quinolones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D015363:Quinolones