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.
Mohri
Kunihiko
K
Showa Pharmaceutical University, Machida, Tokyo, Japan. mohri@ac.shoyaku.ac.jp
Yokoyama
Katsumi
K
Komiya
Hiroaki
H
Watanabe
Yuhya
Y
Yoshida
Yuki
Y
Isobe
Kimiaki
K
Tsuda
Yoshisuke
Y
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