Literature DB >> 21957865

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

Ioulia Gorokhovik1, Luc Neuville, Jieping Zhu.   

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.
© 2011 American Chemical Society

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Year:  2011        PMID: 21957865     DOI: 10.1021/ol202263a

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  Reductive Cyclization of Halo-Ketones to Form 3-Hydroxy-2-Oxindoles via Palladium Catalyzed Hydrogenation: A Hydrogen-Mediated Grignard Addition.

Authors:  Inji Shin; Stephen D Ramgren; Michael J Krische
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

Review 2.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943

  2 in total

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