Dioxopyrrolines. LXII. Diels-Alder reaction of 1-Aryl-4- and 5-methoxycarbonyl-1H-pyrrole-2,3-diones with various 1,3-dienes.
Two new dioxopyrrolines (1-aryl-4-methoxycarbonyl-1H-pyrrole-2,3-dione 6 and the 5-methoxycarbonyl isomer 8) behaved as good dienophiles to some kind of 1,3-dienes examined. In most cases, the products were explained by the reaction where the largest lobe of HOMO of dienes reacted to the larger LUMO of dienophiles in an expected cis-endo manner. However, in the reactions of 8 with alkylbutadienes, piperylene and isoprene, abnormality in the reaction was observed, which was well explained by taking account of steric factors.
Showa Pharmaceutical University, Machida, Tokyo, Japan. mohri@ac.shoyaku.ac.jp
Kunihiko
K
Mohri
Katsumi
K
Yokoyama
Hiroaki
H
Komiya
Yuhya
Y
Watanabe
Yuki
Y
Yoshida
Kimiaki
K
Isobe
Yoshisuke
Y
Tsuda
D003500:Cyclization; D007202:Indicators and Reagents; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
D007202:Indicators and Reagents; D011758:Pyrroles