title: Access to Different Isomeric Dibenzoxazepinones through Copper-Catalyzed C-H Etherification and C-N Bond Construction with Controllable Smiles Rearrangement.
abstract: An efficient new way to access two regio-isomeric dibenzoxazepinones is reported from 8-aminoquinoline benzamides and 2-bromophenols. Through choice of conditions, the reaction proceeds either through a sequential C-H etherification and subsequent Goldberg reaction, both controlled by the aminoquinoline group and Cu(I), or via a C-H etherification and subsequent Smiles rearrangement promoted by Cu(II) and t-BuOK. The 8-aminoquinoline moiety, e.g., 8-amino-5-methoxyquinoline, is readily removable from the structures of dibenzoxazepinones under moderate conditions.
authors.affiliation: CAS Key Laboratory of Receptor Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, P. R. China.
authors.forename: Yunfei
authors.initials: Y
authors.lastname: Zhou
authors.affiliation: CAS Key Laboratory of Receptor Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, P. R. China.
authors.forename: Jianming
authors.initials: J
authors.lastname: Zhu
authors.affiliation: CAS Key Laboratory of Receptor Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, P. R. China.
authors.forename: Bo
authors.initials: B
authors.lastname: Li
authors.affiliation: CAS Key Laboratory of Receptor Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, P. R. China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: CAS Key Laboratory of Receptor Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, P. R. China.
authors.forename: Jia
authors.initials: J
authors.lastname: Feng
authors.affiliation: UCB Biopharma SPRL, Chemin du Foriest , Braine-l'Alleud, Belgium.
authors.forename: Adrian
authors.initials: A
authors.lastname: Hall
authors.affiliation: UCB Biopharma SPRL, Chemin du Foriest , Braine-l'Alleud, Belgium.|Kellogg College, University of Oxford, 60-62 Banbury Road, Oxford, OX2 6PN, United Kingdom.
authors.forename: Jiye
authors.initials: J
authors.lastname: Shi
authors.affiliation: CAS Key Laboratory of Receptor Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, P. R. China.
authors.forename: Weiliang
authors.initials: W
authors.lastname: Zhu
mesh_terms: D000634:Aminoquinolines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003989:Dibenzoxazepines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000634:Aminoquinolines; D003989:Dibenzoxazepines; D010636:Phenols; D003300:Copper