title: Iodo-carbocyclization of electron-deficient alkenes: synthesis of oxindoles and spirooxindoles.
abstract: Cyclisative carbo-iodination of N-alkyl-N-arylacrylamide derivatives (3) in the presence of PhI(OAc)(2)/I(2) afforded functionalized 3-(iodomethyl)-3-substituted-indolin-2-ones (4) in good to excellent yields. With a suitably functionalized linear amide, spirooxindole 8 was prepared in a one-pot fashion via a sequence of iodo-arylation followed by an in situ base-promoted intramolecular S(N)2 reaction.
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
authors.forename: Hai-Long
authors.initials: HL
authors.lastname: Wei
authors.forename: Tiffany
authors.initials: T
authors.lastname: Piou
authors.forename: Jeremy
authors.initials: J
authors.lastname: Dufour
authors.forename: Luc
authors.initials: L
authors.lastname: Neuville
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D004583:Electrons; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis*
chemical_list: D000475:Alkenes; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole