One-Pot Functionalization of 8-Aminoquinolines through the Acylation and Regioselective C5-H Halogenation under Transition-Metal-Free Conditions

被引：7

作者：

Li, Dandan ^{[1
]}

Jia, Zhenzhen ^{[1
]}

Jiang, Yongshuai ^{[1
]}

Jia, Jingpeng ^{[1
]}

Zhao, Xiaowei ^{[1
]}

Li, Zehui ^{[1
]}

Xu, Zhihong ^{[1
]}

机构：

[1] Xuchang Univ, Sch Chem & Chem Engn, 88 Bayi Rd, Xuchang 461000, Henan, Peoples R China

来源：

CHEMISTRYSELECT | 2019年 / 4卷 / 47期

基金：

中国国家自然科学基金;

关键词：

C5-H Halogenation; 8-aminoquinolines; acyl halides; acylation; transition metal free; H BOND FUNCTIONALIZATIONS; N-FLUOROBENZENESULFONIMIDE; C(SP(3))-H BONDS; DIRECTING GROUPS; SODIUM-HALIDES; QUINOLINES; COPPER; IODINATION; ACTIVATION; AMIDES;

D O I：

10.1002/slct.201904286

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mild and efficient functionalization of 8-aminoquinolines has been demonstrated through the acylation and regioselective C5-H halogenation in one pot under transition metal free conditions. This method enables the acyl halides acting as the donors of both acyl and halide atoms. Moremover, different type of acyl halides could be employed in this reaction and proceeded smoothly to afford the corresponding halogenated products in moderate to good yields. The protocol is operationally simple, facile, and might have potential application in synthesis of 5-halogenated quinoline scaffolds.

引用

页码：13964 / 13967

页数：4

共 80 条

[41] Methemoglobinemia Caused by 8-Aminoquinoline Drugs: DFT Calculations Suggest an Analogy to H4B's Role in Nitric Oxide Synthase [J].

Liu, Haining ;

Walker, Larry A. ;

Nanayakkara, N. P. Dhammika ;

Doerksen, Robert J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) :1172-1175

[42] Copper-Catalyzed or -Mediated C-H Bond Functionalizations Assisted by Bidentate Directing Groups [J].

Liu, Jidan ;

Chen, Guoshu ;

Tan, Ze .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (08) :1174-1194

[43] Copper-Mediated ortho-Nitration of Arene and Heteroarene C-H Bonds Assisted by an 8-Aminoquinoline Directing Group [J].

Liu, Jidan ;

Zhuang, Shaobo ;

Gui, Qingwen ;

Chen, Xiang ;

Yang, Zhiyong ;

Tan, Ze .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (04) :732-738

[44] PhI(OAc)2 oxidative C5 halogenation of quinolines using copper halides under mild conditions [J].

Liu, Xing-Xing ;

Wu, Zhao-Yang ;

Luo, Xin-Liang ;

He, Yong-Qin ;

Zhou, Xiao-Qiang ;

Fan, Yu-Xing ;

Huang, Guo-Sheng .

RSC ADVANCES, 2016, 6 (75) :71485-71488

[45] Iron(III)-Catalyzed Highly Regioselective Halogenation of 8-Amidoquinolines in Water [J].

Long, Yang ;

Pan, Lei ;

Zhou, Xiangge .

MOLECULES, 2019, 24 (03)

[46]

Luo ZG, 2009, CHEM RES CHINESE U, V25, P841

[47] Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities [J].

Madrid, PB ;

Sherrill, J ;

Liou, AP ;

Weisman, JL ;

DeRisi, JL ;

Guy, RK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (04) :1015-1018

[48] Asymmetric chroman synthesis via an intramolecular oxy-Michael addition by bifunctional organocatalysts [J].

Miyaji, Ryota ;

Asano, Keisuke ;

Matsubara, Seijiro .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (01) :119-122

[49] A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines [J].

Motati, Damoder Reddy ;

Uredi, Dilipkumar ;

Watkins, E. Blake .

CHEMICAL SCIENCE, 2018, 9 (07) :1782-1788

[50] Highly Potent and Isoform Selective Dual Site Binding Tankyrase/Wnt Signaling Inhibitors That Increase Cellular Glucose Uptake and Have Antiproliferative Activity [J].

Nathubhai, Amit ;

Haikarainen, Teemu ;

Koivunen, Jarkko ;

Murthy, Sudarshan ;

Koumanov, Francoise ;

Lloyd, Matthew D. ;

Holman, Geoffrey D. ;

Pihlajaniemi, Taina ;

Tosh, David ;

Lehtio, Lari ;

Threadgill, Michael D. .

JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (02) :814-820

← 1 2 3 4 5 6 7 8 →