title: One-Pot Synthesis of 5-Amino-2,5-dihydro-1-benzoxepines: Access to Pharmacologically Active Heterocyclic Scaffolds.
abstract: A one-pot multibond-forming process involving a thermally mediated Overman rearrangement and a ring closing metathesis reaction of allylic trichloroacetimidates bearing a 2-allyloxyaryl group has been developed for the synthesis of 5-amino-substituted 2,5-dihydro-1-benzoxepines. Chemoselective reduction and functionalization of these compounds allowed access to a range of pharmacologically active 5-amino-2,3,4,5-tetrahydro-1-benzoxepine scaffolds.
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, The Joseph Black Building, Glasgow G12 8QQ, United Kingdom.
authors.forename: Ewen D D
authors.initials: ED
authors.lastname: Calder
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, The Joseph Black Building, Glasgow G12 8QQ, United Kingdom.
authors.forename: Salaheddin A I
authors.initials: SA
authors.lastname: Sharif
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, The Joseph Black Building, Glasgow G12 8QQ, United Kingdom.
authors.forename: Fiona I
authors.initials: FI
authors.lastname: McGonagle
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, The Joseph Black Building, Glasgow G12 8QQ, United Kingdom.
authors.forename: Andrew
authors.initials: A
authors.lastname: Sutherland
mesh_terms: D001584:Benzoxepins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: C000603391:5-amino-2,5-dihydro-1-benzoxepine; D001584:Benzoxepins; D006571:Heterocyclic Compounds