Synthesis of profluorescent isoindoline nitroxides via palladium-catalysed Heck alkenylation


Autoria(s): Arnold, Dennis; Bottle, Steven; Johnson, Therese; Keddie, Daniel
Data(s)

2005

Resumo

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.

Identificador

http://eprints.qut.edu.au/23836/

Publicador

Royal Society of Chemistry

Relação

DOI:10.1039/B504354A

Arnold, Dennis, Bottle, Steven, Johnson, Therese, & Keddie, Daniel (2005) Synthesis of profluorescent isoindoline nitroxides via palladium-catalysed Heck alkenylation. Organic and Biomolecular Chemistry, 3, pp. 2593-2598.

Fonte

Faculty of Science and Technology

Palavras-Chave #030400 MEDICINAL AND BIOMOLECULAR CHEMISTRY #030500 ORGANIC CHEMISTRY #Nitroxides, Palladium, Heck Reaction
Tipo

Journal Article