Trifluoroacetic acid-promoted synthesis of 3-hydroxy, 3-amino and spirooxindoles from α-keto-N-anilides. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2011

Trifluoroacetic acid-promoted synthesis of 3-hydroxy, 3-amino and spirooxindoles from α-keto-N-anilides.

Résumé

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.

Domaines

Chimie organique
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Dates et versions

hal-00649281 , version 1 (07-12-2011)

Identifiants

Citer

Ioulia Gorokhovik, Luc Neuville, Jieping Zhu. Trifluoroacetic acid-promoted synthesis of 3-hydroxy, 3-amino and spirooxindoles from α-keto-N-anilides.. Organic Letters, 2011, 13 (20), pp.5536-5539. ⟨10.1021/ol202263a⟩. ⟨hal-00649281⟩
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