Microwave-accelerated cross-dehydrogenative-coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile under metal-free conditions

被引：1

作者：

Zhou, Chao ^{[1
]}

Liu, Yunwei ^{[1
]}

Luo, Qi ^{[1
]}

Zhang, Yicheng ^{[1
]}

Zhou, Jingwen ^{[1
]}

Zhang, Haoyu ^{[1
]}

Liu, Jie ^{[1
]}

机构：

[1] Huaibei Normal Univ, Key Lab Green & Precise Synthet Chem, Minist Educ, Huaibei 235000, Anhui, Peoples R China

来源：

RSC ADVANCES | 2023年 / 13卷 / 31期

基金：

中国国家自然科学基金;

关键词：

C-H SULFONYLATION; 8-AMINOQUINOLINE AMIDES; BOND FUNCTIONALIZATIONS; DIRECT ALKYLATION; COPPER; ARYLATION; QUINOLINES; TRIFLUOROMETHYLATION; 8-AMIDOQUINOLINES; PYRIDINES;

D O I：

10.1039/d3ra03651k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly selective remote C(sp(3))-H acetonation of N-(quinolin-8-yl)amide scaffolds at the C5-position under microwave irradiation has been developed. In the absence of a transition-metal-catalyst, benzoyl peroxide (BPO)-promoted cross-dehydrogenation coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile occurred smoothly to generate the corresponding 5-acetonated/acetonitriled N-(quinolin-8-yl)amides in good yields. The transformation is operationally simple, rapid, easily scaled-up to the gram scale, and shows a broad substrate scope.

引用

页码：21231 / 21235

页数：5

共 7 条

[1] Oxidative cross-dehydrogenative coupling between iodoarenes and acylanilides for C-N bond formation under metal-free conditions†
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