title: Trifluoroacetic acid-promoted synthesis of 3-hydroxy, 3-amino and spirooxindoles from α-keto-N-anilides.
abstract: Ketoanilides containing alkyl side chains were readily cyclized to 3-hydroxy-2-oxindoles or spirooxindoles by a single or double intramolecular Friedel-Crafts reaction in the presence of trifluoroacetic acid (TFA) at room temperature or at 45 °C. α-Iminocarboxamides, generated in situ from ketoamides, cyclized similarly to 3-aminooxindoles under identical conditions.
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
authors.forename: Ioulia
authors.initials: I
authors.lastname: Gorokhovik
authors.forename: Luc
authors.initials: L
authors.lastname: Neuville
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000813:Anilides / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D013696:Temperature; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D000813:Anilides; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D014269:Trifluoroacetic Acid