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Communication | Regular issue | Vol 19, No. 11, 1982, pp.2027-2032
Published online, 1st January, 1970
DOI: 10.3987/R-1982-11-2027
Diels-Alder Cycloaddition of 1,3-Disubstituted Butadienes to Isoquinolinopyrrolinediones: Solvent and Temperature Effect on cis-end to cis-exo Isomerization of the Adduct

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

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

Abstract

Diels-Alder cycloaddition of 1,3-disubstituted butadienes to isoquinolinopyrrolinediones gives two cycloadducts, the previously reported cis-endo (regarding the dioxopyrroline ring) adduct and the new cis-exo adduct, with a variable ratio largely depending on the solvent and temperature of the reaction. Determination of their stereochemistries and isomerization experiments proved that the former adduct is a kinetic and the latter adduct is a thermodynamic product. Acceleration of dissociation and recombination of the former to the latter adduct in polar solvents (such as CHCl3) was also suggested.