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Synthesis of 2-hydroxy-3-indolinones and 3-hydroxy-2-indolinones by anionic cyclization, in situ oxidation and rearrangement

Coldham, I., Adams, H., Ashweek, N.J., Barker, T.A., Reeder, A.T. and Skilbeck, M.C. (2010) Synthesis of 2-hydroxy-3-indolinones and 3-hydroxy-2-indolinones by anionic cyclization, in situ oxidation and rearrangement. Tetrahedron Letters, 51 (18). pp. 2457-2460. ISSN 0040-4039

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Abstract

Lithiation with butyllithium of 2-(benzylamino)benzamides (N-benzyl anthranilamides) occurs at the benzylic position to give an alpha-amino-organolithium that cyclizes to the 3-indolinone (indoxyl) ring (similar to a Parham cyclization). Autoxidation in air gives 2-hydroxy-3-indolinones. In the absence of a proton source, rearrangement of the aryl group from C-2 to C-3 occurs to give the 3-hydroxy-2-indolinone (oxindole) ring. (C) 2010 Elsevier Ltd. All rights reserved.

Item Type: Article
Keywords: Intramolecular Carbolithiation Reactions; Catalyzed Asymmetric Addition; Remote Matalation; Directed Ortho; Pyrrolidines; Oxindoles; Indoles; Systems; Esters; Arylation
Institution: The University of Sheffield
Academic Units: The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield)
Depositing User: Miss Anthea Tucker
Date Deposited: 25 May 2010 08:30
Last Modified: 25 May 2010 08:30
Published Version: http://dx.doi.org/10.1016/j.tetlet.2010.02.159
Status: Published
Publisher: Elsevier
Identification Number: 10.1016/j.tetlet.2010.02.159
URI: http://eprints.whiterose.ac.uk/id/eprint/10843

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