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

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• 作者：Yunfei Zhou ; Jianming Zhu ; Bo Li ; Yong Zhang ; Jia Feng ; Adrian Hall ; Jiye Shi ; Weiliang Zhu
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：18
• 期：3
• 页码：380-383
• 全文大小：427K
• ISSN：1523-7052

文摘

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.