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

Autori
Mance, Ana Dunja ; Borovička, Branko ; Jakopčić, Krešimir ; Pavlović, Gordana ; Leban, Ivan

Izvornik
Journal of heterocyclic chemistry (0022-152X) 39 (2002), 2; 277-285

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

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

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemijsko inženjerstvo

POVEZANOST RADA