Copper-promoted oxidative mono- and di-bromination of 8-aminoquinoline amides with HBr and DMSO

被引：0

作者：

Shao, Changdong ^{[1
]}

Liu, Jingyi ^{[1
]}

Shen, Yanan ^{[1
]}

Li, Li ^{[1
]}

Ma, Chen ^{[1
]}

Hu, Zhengsong ^{[1
]}

Kan, Yuhe ^{[1
]}

Chen, Ping ^{[1
]}

Zhang, Tingting ^{[1
]}

机构：

[1] Huaiyin Normal Univ, Sch Chem & Chem Engn, Jiangsu Prov Key Lab Chem Low Dimens Mat, Huaian 223300, Jiangsu, Peoples R China

来源：

RSC ADVANCES | 2025年 / 15卷 / 11期

基金：

中国国家自然科学基金;

关键词：

DIMETHYL-SULFOXIDE; EFFICIENT BROMINATION; C5-H BROMINATION; SODIUM-HALIDES; HALOGENATION; QUINOLINES; FUNCTIONALIZATION; 8-AMIDOQUINOLINES; IODINATION; OLEFINS;

D O I：

10.1039/d5ra00492f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient and convenient method for oxidative mono- and di-bromination of 8-aminoquinoline amides is presented, utilizing hydrogen bromide (HBr) as the brominating reagent and dimethyl sulfoxide (DMSO) as a mild oxidant. Copper salts act as Lewis acid catalysts, facilitating the bromination process. The formation of C5-monobrominated products is promoted by copper sulfate (CuSO4<middle dot>5H2O), whereas the generation of C5, C7-dibrominated products necessitates the participation of copper nitrate (Cu(NO3)2<middle dot>3H2O). A wide range of substrates bearing diverse functional groups undergo smooth transformation, resulting in brominated products with good to excellent yields.

引用

页码：8750 / 8756

页数：7

共 4 条

[1] Copper-promoted C5-selective bromination of 8-aminoquinoline amides with alkyl bromides
Shao, Changdong
Ma, Chen
Li, Li
Liu, Jingyi
Shen, Yanan
Chen, Chen
Yang, Qionglin
Xu, Tianyi
Hu, Zhengsong
Kan, Yuhe
Zhang, Tingting
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 155 - 161
[2] Copper-Promoted Dimethylthiolation of Benzamides under Assistance of 8-Aminoquinoline Group
Guo, Yuanyuan
Liu, Zhenwei
Zhu, Mingxiang
Li, Linlin
Li, Jingya
Zou, Dapeng
Wu, Yusheng
Wu, Yangjie
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (03) : 724 - 730
[3] Copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent
Shao, Changdong
Xu, Tianyi
Chen, Chen
Yang, Qionglin
Tang, Chao
Chen, Ping
Lu, Mingzhu
Hu, Zhengsong
Hu, Huayou
Zhang, Tingting
RSC ADVANCES, 2023, 13 (10) : 6993 - 6999
[4] Selective Mono- and Di-C(aryl)-H Sulfenylation of Benzamides by One-Pot Assembly of 8-Aminoquinoline, Benzoyl chlorides, and Thiophenols
Liu, Yunyun
Huang, Meiying
Wei, Li
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (01) : 41 - 43

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