Cycloaddition of 2(1H)-pyridones having a methoxycarbonyl group to 1,3-butadiene derivatives.
The cycloaddition of 4-methoxycarbonyl-2(1H)-pyridones to silyloxydienes gave isoquinolone derivatives in reasonable yields. Furthermore, the cycloaddition of 6-methoxycarbonyl-2(1H)-pyridones to 2,3-dimethyl-1,3-butadiene produced cycloadducts (isoquinolone and quinolone derivatives) and double cycloadducts (phenanthridone derivatives). The activation energies using Gaussian 98 with RHF/3-21G level of 4- and 6-methoxycarbonyl-2(1H)-pyridones coincided with the experimental facts.
Fujita
R
R
Tohoku Pharmaceutical University, Sendai, Japan. refujita@tohoku-pharm.ac.jp
Hoshino
M
M
Tomisawa
H
H
Matsuzaki
H
H
Hongo
H
H
D002070:Butadienes / Q000138:chemical synthesis* / Q000494:pharmacology; D002855:Chromatography, Thin Layer; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D011728:Pyridones / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared
D002070:Butadienes; D007202:Indicators and Reagents; D011728:Pyridones