Coldham, I., Adams, H., Ashweek, N.J. et al. (3 more authors) (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
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.
Metadata
| Item Type: | Article |
|---|---|
| Authors/Creators: |
|
| Keywords: | Intramolecular Carbolithiation Reactions; Catalyzed Asymmetric Addition; Remote Matalation; Directed Ortho; Pyrrolidines; Oxindoles; Indoles; Systems; Esters; Arylation |
| Dates: |
|
| 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 |
| Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:10843 |
CORE (COnnecting REpositories)
CORE (COnnecting REpositories)