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Access to Different Isomeric Dibenzoxazepinones through Copper-Catalyzed C–H Etherification and C–N Bond Construction with Controllable Smiles Rearrangement

Author:
Zhou, Yunfei, Zhu, Jianming, Li, Bo, Zhang, Yong, Feng, Jia, Hall, Adrian, Shi, Jiye, Zhu, Weiliang
Source:
Organic letters 2016 v.18 no.3 pp. 380-383
ISSN:
1523-7052
Subject:
aminoquinolines, benzamides, chemical bonding, chemical reactions, copper, moieties
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.
Agid:
5792266