Copper(II)-Catalyzed Direct Azidation of N-Acylated 8-Aminoquinolines by Remote C-H Activation

被引：52

作者：

Dou, Yandong ^{[1
]}

Xie, Zhenda ^{[1
]}

Sun, Zongguo ^{[1
]}

Fang, Hongli ^{[1
]}

Shen, Chao ^{[2
]}

Zhang, Pengfei ^{[3
]}

Zhu, Qing ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Biotechnol & Bioengn, Key Lab Bioorgan Synth Zhejiang Prov, Hangzhou 310014, Zhejiang, Peoples R China

[2] Zhejiang Shuren Univ, Coll Biol & Environm Engn, Hangzhou, Zhejiang, Peoples R China

[3] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou, Zhejiang, Peoples R China

来源：

CHEMCATCHEM | 2016年 / 8卷 / 23期

基金：

中国国家自然科学基金;

关键词：

azides; C-H activation; copper; nitrogen heterocycles; regioselectivity; STAUDINGER LIGATION; ARYL AZIDES; COMBINATION REACTIONS; MILD CONDITIONS; REAGENTS; CARBONYLATION; QUINOLINES; INHIBITORS; DISCOVERY; CATALYSIS;

D O I：

10.1002/cctc.201600874

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A simple and efficient copper(II)-catalyzed C5 azidation of N-acylated 8-aminoquinolines by remote C-H activation was developed. On the basis of this reaction, a series of new C5-azidated 8-amidequinolines were synthesized in moderate to good yields.

引用

页码：3570 / 3574

页数：5

共 40 条

[1] Abegg D., 2015, Angew. Chem, V127
[2] Proteome-Wide Profiling of Targets of Cysteine reactive Small Molecules by Using Ethynyl Benziodoxolone Reagents
Abegg, Daniel
Frei, Reto
Cerato, Luca
Hari, Durga Prasad
Wang, Chao
Waser, Jerome
Adibekian, Alexander
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (37) : 10852 - 10857
[3] Azad C. S., 2015, RSC ADV, V5, P100223
[4] Discovery of 4-Amino-8-quinoline Carboxamides as Novel, Submicromolar Inhibitors of NAD-Hydrolyzing Enzyme CD38
Becherer, J. David
Boros, Eric E.
Carpenter, Tiffany Y.
Cowan, David J.
Deaton, David N.
Haffner, Curt D.
Jeune, Michael R.
Kaldor, Istvan W.
Poole, J. Chuck
Preugschat, Frank
Rheault, Tara R.
Schulte, Christie A.
Shearer, Barry G.
Shearer, Todd W.
Shewchuk, Lisa M.
Smalley, Terrence L., Jr.
Stewart, Eugene L.
Stuart, J. Darren
Ulrich, John C.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (17) : 7021 - 7056
[5] Facile and efficient synthesis of 4-azidotetrafluoroaniline: A new photoaffinity reagent
Chehade, KAH
Spielmann, HP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) : 4949 - 4953
[6] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant
Chen, Xiao
Hao, Xue-Shi
Goodhue, Charles E.
Yu, Jin-Quan
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6790 - 6791
[7] Importance of the Dimethylamino Functionality on a Multifunctional Framework for Regulating Metals, Amyloid-β, and Oxidative Stress in Alzheimer's Disease
Derrick, Jeffrey S.
Kerr, Richard A.
Korshavn, Kyle J.
McLane, Michael J.
Kang, Juhye
Nam, Eunju
Ramamoorthy, Ayyalusamy
Ruotolo, Brandon T.
Lim, Mi Hee
[J]. INORGANIC CHEMISTRY, 2016, 55 (10) : 5000 - 5013
[8] Alkene Trifluoromethylation-Initiated Remote α-Azidation of Carbonyl Compounds toward Trifluoromethyl γ-Lactam and Spirobenzofuranone-Lactam
Huang, Lin
Lin, Jin-Shun
Tan, Bin
Liu, Xin-Yuan
[J]. ACS CATALYSIS, 2015, 5 (05): : 2826 - 2831
[9] Manganese-Catalyzed Late-Stage Aliphatic C-H Azidation
Huang, Xiongyi
Bergsten, Tova M.
Groves, John T.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (16) : 5300 - 5303
[10] A Radical Procedure for the Anti-Markovnikov Hydroazidation of Alkenes
Kapat, Ajoy
Koenig, Andreas
Montermini, Florian
Renaud, Philippe
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (35) : 13890 - 13893

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