Trifluoroacetic Acid-Promoted Synthesis of 3-Hydroxy, 3-Amino and Spirooxindoles from α-Keto-N-Anilides

Gorokhovik, IouliaNeuville, LucZhu, Jieping2011-10-202011-10-202011-10-20201110.1021/ol202263ahttps://infoscience.epfl.ch/handle/20.500.14299/71804WOS:000295817100032Ketoanilides 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 degrees C. alpha-Iminocarboxamides, generated in situ from ketoamides, cyclized similarly to 3-aminooxindoles under identical conditions.Friedel-Crafts ReactionStereoselective-SynthesisAsymmetric-SynthesisDomino ProcessOxindolesCyclizationAccess3-Hydroxy-2-OxindolesConstructionSequenceTrifluoroacetic Acid-Promoted Synthesis of 3-Hydroxy, 3-Amino and Spirooxindoles from α-Keto-N-Anilidestext::journal::journal article::research article