Ritchie, B.L., Longcake, A. orcid.org/0000-0003-2881-3938 and Coldham, I. orcid.org/0000-0003-4602-6292 (2025) Preparation of spirocyclic oxindoles by cyclisation of an oxime to a nitrone and dipolar cycloaddition. Beilstein Journal of Organic Chemistry, 21 (1). pp. 1890-1896. ISSN: 1860-5397
Abstract
Oxindoles are an important class of compounds with significant biological activities. Spirocyclic derivatives are present in a variety of natural products. We describe here the formation of spirooxindoles using an intermolecular nitrone cycloaddition reaction. The nitrone dipole was prepared in situ by cyclisation of an oxime, itself prepared in situ from an aldehyde. The stereochemistry of one of the spirooxindoles was determined by single crystal X-ray diffraction studies via crystallisation using encapsulated nanodroplet crystallisation (ENaCt) protocols. The chemistry involves cascade or tandem condensation, cyclisation, and cycloaddition as an efficient strategy for the rapid formation of complex spirocyclic products that could have value for the formation of novel, bioactive oxindoles.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2025 Ritchie et al.; licensee Beilstein-Institut. This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material. |
Keywords: | cascade; cycloaddition; oxindole; spirocycle; stereochemistry |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Psychology (Sheffield) |
Date Deposited: | 29 Sep 2025 14:31 |
Last Modified: | 29 Sep 2025 16:10 |
Status: | Published |
Publisher: | Beilstein Institut |
Refereed: | Yes |
Identification Number: | 10.3762/bjoc.21.146 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:232327 |