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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.

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

Journal Article Type Article
Acceptance Date Jan 6, 2015
Online Publication Date Jan 13, 2015
Publication Date Jun 1, 2015
Deposit Date Dec 1, 2015
Publicly Available Date Dec 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
DOI https://doi.org/10.1016/j.bmc.2015.01.010
Keywords Seven-Membered Rings, Azepane, Oxepane, Diazocarbonyl, Medicinal Chemistry
Public URL http://eprints.nottingham.ac.uk/id/eprint/30957
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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A Nortcliffe and CJ Moody, Bioorg Med Chem, 2015, 23, 2730-2735.pdf (340 Kb)
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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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