Edeson, S.J., Maduli, E.J.M., Swanson, S. et al. (2 more authors) (2016) Investigation of a Late-Stage Derivatization Approach to Isatogens: Discovery of New Reaction Pathways. European Journal of Organic Chemistry, 2016 (1). pp. 83-86. ISSN 1434-193X
Abstract
We have developed a new strategy for preparing 2-substituted indolone N-oxides (isatogens) by substitution reactions with aryl- and alkyl-organometallic reagents. This approach allows a range of substituents to be incorporated at a late stage and complements existing methods that necessitate their early stage incorporation during substrate preparation. Further chemistry has been found to take place at the nitrone moiety; intramolecular dipolar cycloaddition provides access to angularly fused tricyclic heterocycles. More unusually however, these compounds are prone to further addition by organozinc reagents leading to 2,2-disubstituted 3-oxindole products.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
Keywords: | Synthetic methods; Fused-ring systems; Nitrogen heterocycles |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 15 Feb 2016 16:46 |
Last Modified: | 15 Feb 2016 16:46 |
Published Version: | http://dx.doi.org/10.1002/ejoc.201501372 |
Status: | Published |
Publisher: | Wiley-VCH Verlag |
Refereed: | Yes |
Identification Number: | 10.1002/ejoc.201501372 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:94745 |