Seven-membered ring scaffolds for drug discovery: access to functionalised azepanes and oxepanes through diazocarbonyl chemistry
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 o...
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| Format: | Article |
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Elsevier
2015
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| Online Access: | https://eprints.nottingham.ac.uk/30957/ |
| _version_ | 1848794099155468288 |
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| author | Nortcliffe, Andrew Moody, Christopher J. |
| author_facet | Nortcliffe, Andrew Moody, Christopher J. |
| author_sort | Nortcliffe, Andrew |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T19:10:48Z |
| format | Article |
| id | nottingham-30957 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:10:48Z |
| publishDate | 2015 |
| publisher | Elsevier |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-309572020-05-04T17:01:06Z https://eprints.nottingham.ac.uk/30957/ Seven-membered ring scaffolds for drug discovery: access to functionalised azepanes and oxepanes through diazocarbonyl chemistry Nortcliffe, Andrew Moody, Christopher J. 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. Elsevier 2015-01-13 Article PeerReviewed 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 Seven-Membered Rings Azepane Oxepane Diazocarbonyl Medicinal Chemistry http://dx.doi.org/10.1016/j.bmc.2015.01.010 doi:10.1016/j.bmc.2015.01.010 doi:10.1016/j.bmc.2015.01.010 |
| spellingShingle | Seven-Membered Rings Azepane Oxepane Diazocarbonyl Medicinal Chemistry Nortcliffe, Andrew Moody, Christopher J. Seven-membered ring scaffolds for drug discovery: access to functionalised azepanes and oxepanes through diazocarbonyl chemistry |
| title | Seven-membered ring scaffolds for drug discovery: access to functionalised azepanes and oxepanes through diazocarbonyl chemistry |
| title_full | Seven-membered ring scaffolds for drug discovery: access to functionalised azepanes and oxepanes through diazocarbonyl chemistry |
| title_fullStr | Seven-membered ring scaffolds for drug discovery: access to functionalised azepanes and oxepanes through diazocarbonyl chemistry |
| title_full_unstemmed | Seven-membered ring scaffolds for drug discovery: access to functionalised azepanes and oxepanes through diazocarbonyl chemistry |
| title_short | Seven-membered ring scaffolds for drug discovery: access to functionalised azepanes and oxepanes through diazocarbonyl chemistry |
| title_sort | seven-membered ring scaffolds for drug discovery: access to functionalised azepanes and oxepanes through diazocarbonyl chemistry |
| topic | Seven-Membered Rings Azepane Oxepane Diazocarbonyl Medicinal Chemistry |
| url | https://eprints.nottingham.ac.uk/30957/ https://eprints.nottingham.ac.uk/30957/ https://eprints.nottingham.ac.uk/30957/ |