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Synthesis of profluorescent isoindoline nitroxides via palladium-catalysed Heck alkenylation

By Dennis Arnold, Steven Bottle, Therese Johnson and Daniel Keddie

Abstract

The synthesis of a new structural class of isoindoline nitroxides (aminoxyls), accessible via the palladium-catalysed Heck reaction, is presented. Reaction of the aryl bromoamine, 5-bromo-1,1,3,3-tetramethylisoindoline (4) or dibromoamine, 5,6-dibromo-1,1,3,3-tetramethylisoindoline (5) or the analogous bromonitroxides 6 and 7 with methyl acrylate gives the acrylate substituted tetramethylisoindoline amines 8 and 10 and nitroxides 12 and 14. Similarly, the reaction of the aryl bromides and dibromides 4–7 with methyl 4-vinylbenzoate gives the carboxystyryl substituted tetramethylisoindoline amines 9 and 11 and the analogous nitroxides 13 and 15. The carboxystyryl tetramethylisoindoline nitroxides demonstrate strongly suppressed fluorescence, which is revealed upon removal of the free radical by reduction or radical coupling

Topics: 030400 MEDICINAL AND BIOMOLECULAR CHEMISTRY, 030500 ORGANIC CHEMISTRY, Nitroxides, Palladium, Heck Reaction
Publisher: Royal Society of Chemistry
Year: 2005
DOI identifier: 10.1039/B504354A
OAI identifier: oai:eprints.qut.edu.au:23836
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