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

被引：29

作者：

Zhou, Yunfei ^{[1
]}

Zhu, Jianming ^{[1
]}

Li, Bo ^{[1
]}

Zhang, Yong ^{[1
]}

Feng, Jia ^{[1
]}

Hall, Adrian ^{[2
]}

Shi, Jiye ^{[2
,3
]}

Zhu, Weiliang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Design Ctr, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China

[2] UCB Biopharma SPRL, Chemin Foriest, Braine Lalleud, Belgium

[3] Univ Oxford, Kellogg Coll, 60-62 Banbury Rd, Oxford OX2 6PN, England

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 03期

基金：

上海市自然科学基金;

关键词：

PALLADIUM; ACID; FUNCTIONALIZATION; BENZAMIDES; C(SP(3))-H; AMINATION; ARYLATION; SP(2);

D O I：

10.1021/acs.orglett.5b03378

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：380 / 383

页数：4

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