title: Metal-catalyzed rearrangements of 3-allenyl 3-hydroxyindolin-2-ones in the presence of halogenated reagents.
abstract: 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.
authors: 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. alcaideb@quim.ucm.es
authors: Benito
authors: B
authors: Alcaide
authors: Pedro
authors: P
authors: Almendros
authors: Amparo
authors: A
authors: Luna
authors: Natividad
authors: N
authors: Prieto
mesh_terms: D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D003500:Cyclization; D005290:Ferric Compounds / Q000737:chemistry; D006046:Gold / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D000078183:Oxindoles; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry; D012834:Silver / Q000737:chemistry
chemical_list: C436753:3-hydroxyindolin-2-one; D002712:Chlorides; D005290:Ferric Compounds; D006846:Hydrocarbons, Halogenated; D007211:Indoles; D009942:Organometallic Compounds; D000078183:Oxindoles; D011804:Quinolines; C022960:2-oxindole; D012834:Silver; D006046:Gold; C024555:ferric chloride