Diels-Alder reaction of 1,3-butadiene derivatives with 1-methyl-2(1H)-quinolones having an electron-withdrawing group at the 4-position.
Diels-Alder reactions of 1-methyl-2(1H)-quinolones having an electron-withdrawing group at the 4-position with isoprene, butadiene sulfone, and cyclohexadiene were performed to yield functionalized phenanthridones stereoselectively at atmospheric and at high pressure. Regioselectivity and stereochemistry of a methoxycarbonyl group were studied using the semi-empirical and ab initio MO methods, respectively.
Fujita
R
R
Tohoku Pharmaceutical University, Sendai, Japan. refujita@tohoku-pharm.ac.jp
Watanabe
K
K
Yoshisuji
T
T
Hongo
H
H
Matsuzaki
H
H
D001274:Atmospheric Pressure; D002070:Butadienes / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003510:Cyclohexanes; D053138:Cyclohexenes; D004583:Electrons; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015363:Quinolones / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
D002070:Butadienes; D003510:Cyclohexanes; D053138:Cyclohexenes; D007202:Indicators and Reagents; D015363:Quinolones; C048401:1,4-cyclohexadiene; C031763:1,3-butadiene