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Communication | Regular issue | Vol 19, No. 11, 1982, pp.2053-2056
Published online, 1st January, 1970
DOI: 10.3987/R-1982-11-2053
Δ2-Pyrroline-4,5-dione, and Ambident Dienophile in Diels-Alder Reaction

Yoshisuke Tsuda, Takeshi Ohshima, Takehiro Sano, and Jun Toda

*School of Pharmacy, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan


Thermal cycloaddition of activated 1,3-butadienes to benzazepinopyrrolinedione 4 took place to C=O instead of C=C in the enone system, yielding dihydropyrane derivatives. The change of reactivity compared to isoquinolinopyrrolinedione 1 was attributed to the steric hindrance on C=C of the enone due to non-planarity of the aromatic ring and the dioxopyrroline ring.