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Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain
; Fax: +34-91-3944103
Instituto de Química Orgánica General, IQOG, Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva 3, 28006-Madrid, Spain
; Fax: +34-91-5644853
Org. Biomol. Chem., 2013,11, 1216-1225
20 Sep 2012,
14 Dec 2012
First published online
14 Dec 2012
The reactions of 3-allenyl 3-hydroxyoxindoles with a variety of halogenated reagents in the presence of catalytic amounts of precious metal salts were explored. Both, rearrangement and oxycyclization reactions to give 4-(1-halovinyl)-quinolinediones or spirocyclic halooxindoles, respectively, are competitive pathways. The kind of functionalization is substrate and reaction conditions dependent.
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Organic & Biomolecular Chemistry
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