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

Nortcliffe, Andrew; Moody, Christopher J.

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: https://nottingham-repository.worktribe.com/output/743375
• Publisher URL: http://dx.doi.org/10.1016/j.bmc.2015.01.010
• 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.