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

Nortcliffe, Andrew and Moody, Christopher J. (2015) Seven-membered ring scaffolds for drug discovery: access to functionalised azepanes and oxepanes through diazocarbonyl chemistry. Bioorganic and Medicinal Chemistry, 23 (11). pp. 2730-2735. ISSN 1464-3391

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Abstract

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.

Item Type: Article
RIS ID: https://nottingham-repository.worktribe.com/output/743375
Keywords: Seven-Membered Rings, Azepane, Oxepane, Diazocarbonyl, Medicinal Chemistry
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: https://doi.org/10.1016/j.bmc.2015.01.010
Depositing User: Bramwell, Roseanna
Date Deposited: 01 Dec 2015 10:57
Last Modified: 04 May 2020 17:01
URI: http://eprints.nottingham.ac.uk/id/eprint/30957

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