Synthesis of phenanthridones using Diels-Alder reactions of 4-substituted 2(1H)-quinolones acting as dienophiles.
Diels-Alder reactions of 2(1H)-quinolones having an electron-withdrawing group at the 4-position with 1,3-butadiene derivatives were carried out to give the phenanthridones richly functionalized under the conditions of atmospheric and high pressure. Furthermore, the reactivities of 4-substituted 2(1H)-quinolones acting as a dienophile were examined using MO calculation.
Fujita
R
R
Tohoku Pharmaceutical University, Sendai, Japan. refujita@tohoku-pharm.ac.jp
Watanabe
K
K
Yoshisuji
T
T
Matsuzaki
H
H
Harigaya
Y
Y
Hongo
H
H
D000399:Air Pressure; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D008958:Models, Molecular; D008968:Molecular Conformation; D010617:Phenanthridines / Q000138:chemical synthesis*; D011804:Quinolines / Q000737:chemistry*
D010617:Phenanthridines; D011804:Quinolines