Novel Diels-Alder reaction of 4-nitro-1(2H)-isoquinolones.
A novel Diels-Alder (DA) reaction with 4-nitro-1(2H)-isoquinolones acting as the dienophile afforded 5(6H)-phenanthridone derivatives. The DA reaction of 4-nitro-1(2H)-isoquinolone with 1-methoxy-1,3-butadiene gave biologically active 5(6H)-phenanthridone possessing in a high yield. Regioselectivity of 4-nitro-1(2H)-isoquinolones with 1-methoxy-3-silyloxy-1,3-butadiene was calculated using molecular orbital (MO) calculations.
Fujita
Reiko
R
Tohoku Pharmaceutical University, Sendai, Japn. refujita@tohoku-pharm.ac.jp
Wakayanagi
Sota
S
Wakamatsu
Hideaki
H
Matsuzaki
Hisao
H
D002070:Butadienes / Q000737:chemistry; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002855:Chromatography, Thin Layer; D007202:Indicators and Reagents; D007546:Isoquinolines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009574:Nitro Compounds / Q000138:chemical synthesis*; D017550:Spectroscopy, Fourier Transform Infrared
D002070:Butadienes; D007202:Indicators and Reagents; D007546:Isoquinolines; D009574:Nitro Compounds; C078288:2-methoxy-1,3-butadiene