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Seven-membered ring scaffolds for drug discovery: Access to functionalised azepanes and oxepanes through diazocarbonyl chemistry

Nortcliffe, Andrew; Moody, Christopher J.

Authors

Christopher J. Moody



Abstract

© 2015 Elsevier Ltd. All rights reserved. Functionalised azepane and oxepane scaffolds were prepared using diazocarbonyl chemistry and elaborated to show their potential use in library synthesis. Key dicarbonyl containing seven-membered rings were functionalised via diastereoselective Luche reduction of the ketone followed by manipulation of the ester and amine groups. Further scaffolds could be accessed by C-alkylation of the dicarbonyl compounds. In addition, an oxepane containing amino acid could be prepared via a diastereoselective enamine reduction.

Journal Article Type Article
Publication Date Jun 1, 2015
Journal Bioorganic and Medicinal Chemistry
Print ISSN 0968-0896
Electronic ISSN 1464-3391
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 23
Issue 11
Pages 2730-2735
APA6 Citation Nortcliffe, A., & Moody, C. J. (2015). Seven-membered ring scaffolds for drug discovery: Access to functionalised azepanes and oxepanes through diazocarbonyl chemistry. Bioorganic and Medicinal Chemistry, 23(11), 2730-2735. https://doi.org/10.1016/j.bmc.2015.01.010
DOI https://doi.org/10.1016/j.bmc.2015.01.010
Keywords Seven-Membered Rings, Azepane, Oxepane, Diazocarbonyl, Medicinal Chemistry
Publisher URL http://dx.doi.org/10.1016/j.bmc.2015.01.010
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc-nd/4.0
Additional Information This article is maintained by: Elsevier; Article Title: Seven-membered ring scaffolds for drug discovery: Access to functionalised azepanes and oxepanes through diazocarbonyl chemistry; Journal Title: Bioorganic & Medicinal Chemistry; CrossRef DOI link to publisher maintained version: https://doi.org/10.1016/j.bmc.2015.01.010; Content Type: article; Copyright: Copyright © 2015 Elsevier Ltd. All rights reserved.

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc-nd/4.0





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