engleski

New Compounds in Ring-opening Reaction of 5-Substituted Epoxyisoindolines

Methoxy or nitro group present in furan ring of tertiary alkenylfurfurylamine changes the expected results of both, the intramolecular [4+2]cycloaddition and the acid catalyzed ring- opening reaction derived oxatricycloadduct. With a 5-methoxy group, inaddition to the expected 5-methoxyisoindoline 3, the corresponding hydroxy derivative 5 wasobtained.On the other hand a 5-nitro group changes the outcomeof the reaction even more profoundly.Instead of theexpected 5-nitroisoindoline 12, 5-nitro-substituted epoxyisoindoline 6 submitted to ring-opening reaction with the mixture of hydrobromic and acetic acid, yielded the mixture of bromo-substituted epoxy compounds 7, 8, 9, and/or bromo-substituted isoindolines 10 and 11.

epoxyisoindoline; isoindoline; hexahydroisoindoline; acid catalyzed ring-opening reaction

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