Copper-Catalyzed One-Pot N-Acylation and C5-H Halogenation of 8-Aminoquinolines: The Dual Role of Acyl Halides

被引：42

作者：

Du, Yi ^{[1
]}

Liu, Yunyun ^{[1
]}

Wan, Jie-Ping ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 06期

基金：

中国国家自然科学基金;

关键词：

C-H FUNCTIONALIZATION; REGIOSELECTIVE HALOGENATION; QUINOLINE DERIVATIVES; CHLORIDES; AMIDES; MILD; SODIUM; ACTIVATION; STRATEGY; AMINES;

D O I：

10.1021/acs.joc.8b00068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of N-acyl-5-halo-8-aminoquino-lines has been realized by directly employing 8-aminoquino-lines and acyl halides (Cl, Br, I) with copper catalysis. The construction of the target products involves domino N-acylation and C5-H halogenations of the 8-aminoquinoline, wherein the acyl halides act as the donors of both acyl and halide atoms, which enables the first access to the step efficient synthesis of 5-halogenated N-acyl quinlolines.

引用

页码：3403 / 3408

页数：6

共 75 条

[1] Synergistic Photoredox/Nickel Coupling of Acyl Chlorides with Secondary Alkyltrifluoroborates: Dialkyl Ketone Synthesis [J].

Amani, Javad ;

Molander, Gary A. .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (03) :1856-1863

[2] Visible Light Photoredox Cross-Coupling of Acyl Chlorides with Potassium Alkoxymethyltrifluoroborates: Synthesis of α-Alkoxyketones [J].

Amani, Javad ;

Sodagar, Esmat ;

Molander, Gary A. .

ORGANIC LETTERS, 2016, 18 (04) :732-735

[3] Fukuyama Reduction and Integrated Thioesterification/Fukuyama Reduction of Thioesters and Acyl Chlorides Using Continuous Flow [J].

Asadi, Mousa ;

Bonke, Shannon ;

Poyzos, Anastasios ;

Lupton, David W. .

ACS CATALYSIS, 2014, 4 (06) :2070-2074

[4] Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions [J].

Barluenga, Jose ;

Rodriguez, Felix ;

Fananas, Francisco J. .

CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) :1036-1048

[5] Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N- Heterocyclization [J].

Chelucci, Giorgio ;

Porcheddu, Andrea .

CHEMICAL RECORD, 2017, 17 (02) :200-216

[6] Nickel-Catalyzed Site-Selective C-H Bond Difluoroalkylation of 8-Aminoquinolines on the C5-Position [J].

Chen, Hao ;

Li, Pinhua ;

Wang, Min ;

Wang, Lei .

ORGANIC LETTERS, 2016, 18 (19) :4794-4797

[7] Metal-free C5-selective halogenation of quinolines under aqueous conditions [J].

Chen, Jichao ;

Wang, Tianyu ;

Liu, Yanpeng ;

Wang, Tong ;

Lin, Aijun ;

Yao, Hequan ;

Xu, Jinyi .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (04) :622-626

[8] Palladium-Catalyzed Aerobic Oxidative Coupling of Acyl Chlorides with Arylboronic Acids [J].

Chen, Jiuxi ;

Peng, Yong ;

Liu, Miaochang ;

Ding, Jinchang ;

Su, Weike ;

Wu, Huayue .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (11-12) :2117-2122

[9] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[10] Iron-Catalyzed, Chelation-Induced Remote C-H Allylation of Quinolines via 8-Amido Assistance [J].

Cong, Xuefeng ;

Zeng, Xiaoming .

ORGANIC LETTERS, 2014, 16 (14) :3716-3719

← 1 2 3 4 5 6 7 8 →