title: Seven-membered ring scaffolds for drug discovery: Access to functionalised azepanes and oxepanes through diazocarbonyl chemistry.
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.
authors: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.
authors: Andrew
authors: A
authors: Nortcliffe
authors: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK. Electronic address: c.j.moody@nottingham.ac.uk.
authors: Christopher J
authors: CJ
authors: Moody
mesh_terms: D000478:Alkylation; D001381:Azepines / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D055808:Drug Discovery; D008958:Models, Molecular; D015394:Molecular Structure; D010082:Oxepins / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001381:Azepines; D001391:Azo Compounds; D010082:Oxepins
keywords: Azepane; Diazocarbonyl; Medicinal chemistry; Oxepane; Seven-membered rings