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New compounds in ring-opening reaction of 5-substituted epoxyisoindolines

✍ Scribed by Ana Dunja Mance; Branko Borovička; KreŠImir Jakopčić; Gordana Pavlović; Ivan Leban

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
92 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Methoxy or nitro group present in the furan ring of tertiary alkenylfurfurylamine changes the expected results of both, the intramolecular [4+2]cycloaddition and the acid catalyzed ring‐opening reaction of the derived oxatricycloadduct. With a 5‐methoxy group, in addition to the expected 5‐methoxyisoindoline 3, the corresponding hydroxy derivative 5 was obtained. On the other hand a 5‐nitro group changes the outcome of the reaction even more profoundly. Instead of the expected 5‐nitroisoindoline 12, 5‐nitro‐substituted epoxy‐isoindoline 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.

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