Metal-Free, Oxidant-Free, Site-Selective C-H Halogenations to Aminoquinolines at Room Temperature using N-Halosaccharins

被引：18

作者：

Dutta, Himangsu Sekhar ^{[1
]}

Khan, Bhuttu ^{[1
]}

Khan, Afsar Ali ^{[1
]}

Raziullah ^{[1
]}

Ahmad, Ashfaq ^{[1
]}

Kant, Ruchir ^{[2
]}

Koley, Dipankar ^{[1
]}

机构：

[1] Cent Drug Res Inst, Med & Proc Chem Div, CSIR, Lucknow 226031, Uttar Pradesh, India

[2] Cent Drug Res Inst, Mol & Struct Biol Div, CSIR, Lucknow 226031, Uttar Pradesh, India

来源：

CHEMISTRYSELECT | 2017年 / 2卷 / 22期

关键词：

C-H functionalization; halogenations; late stage drug molecule diversification; metal-free; quinoline; REMOTE C; REGIOSELECTIVE HALOGENATION; 8-AMINOQUINOLINE AMIDES; DIRECTING GROUP; DIRECT ALKYLATION; SODIUM-HALIDES; COPPER; QUINOLINES; ARYLATION; QUINAZOLINE;

D O I：

10.1002/slct.201701649

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a metal-free, oxidant-free, highly regioselective halogenations protocol (chlorination, bromination and iodination) to amidoquinolines using N-halosaccharin derivatives. Various amidoquinolines are tolerated by the method and delivered C5-haloamidoquinoline derivates in excellent yields. A homo and hetero bis-halogenation protocol has also been established. Late stage drug molecule diversification has also been demonstrated using the developed protocol.

引用

页码：6488 / 6492

页数：5

共 79 条

[41] Quinoline, quinazoline and acridone alkaloids [J].

Michael, JP .

NATURAL PRODUCT REPORTS, 2004, 21 (05) :650-668

[42] Quinoline, quinazoline and acridone alkaloids [J].

Michael, JP .

NATURAL PRODUCT REPORTS, 2003, 20 (05) :476-493

[43] Quinoline, quinazoline and acridone alkaloids [J].

Michael, JP .

NATURAL PRODUCT REPORTS, 1999, 16 (06) :697-709

[44] 4-Position-Selective C-H Perfluoroalkylation and Perfluoroarylation of Six-Membered Heteroaromatic Compounds [J].

Nagase, Masahiro ;

Kuninobu, Yoichiro ;

Kanai, Motomu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (19) :6103-6106

[45] Copper-Mediated C-H/C-H Biaryl Coupling of Benzoic Acid Derivatives and 1,3-Azoles [J].

Nishino, Mayuko ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (16) :4457-4461

[46] Ammosamide D, an Oxidatively Ring Opened Ammosamide Analog from a Marine-Derived Streptomyces variabilis [J].

Pan, Ende ;

Jamison, Matthew ;

Yousufuddin, Muhammed ;

MacMillan, John B. .

ORGANIC LETTERS, 2012, 14 (09) :2390-2393

[47] Merging Photoredox Catalysis with Iron(III) Catalysis: C5-H Bromination and Iodination of 8-Aminoquinoline Amides in Water [J].

Qiao, Huijie ;

Sun, Suyan ;

Yang, Fan ;

Zhu, Yu ;

Kang, Jianxun ;

Wu, Yusheng ;

Wu, Yangjie .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (11) :1976-1980

[48] Copper-Mediated Remote Highly Site-Selective C-H Bond Bromination and Chlorination of Quinolines at the C5 Position that is Geometrically Difficult to Access [J].

Rao, Naidu Sambasiva ;

Reddy, Ganapam Manohar ;

Sridhar, B. ;

Sarma, Maheswaran Harihara .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (03) :438-442

[49] Palladium-Catalyzed C-2 Selective Arylation of Quinolines [J].

Ren, Xiaoyu ;

Wen, Ping ;

Shi, Xiaokang ;

Wang, Yuling ;

Li, Jian ;

Yang, Sizhuo ;

Yan, Hao ;

Huang, Guosheng .

ORGANIC LETTERS, 2013, 15 (20) :5194-5197

[50] A General Method for Aminoquinoline-Directed, Copper-Catalyzed sp2 C-H Bond Amination [J].

Roane, James ;

Daugulis, Olafs .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (13) :4601-4607

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