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

[img]
Preview
PDF - Requires a PDF viewer such as GSview, Xpdf or Adobe Acrobat Reader
Available under Licence Creative Commons Attribution Non-commercial No Derivatives.
Download (340kB) | Preview

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
Keywords: Seven-Membered Rings, Azepane, Oxepane, Diazocarbonyl, Medicinal Chemistry
Schools/Departments: University of Nottingham UK Campus > 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: 14 Sep 2016 00:14
URI: http://eprints.nottingham.ac.uk/id/eprint/30957

Actions (Archive Staff Only)

Edit View Edit View