C8-Selective Acylation of Quinoline N-Oxides with α-Oxocarboxylic Acids via Palladium-Catalyzed Regioselective C-H Bond Activation

被引：70

作者：

Chen, Xiaopei ^{[1
]}

Cui, Xiuling ^{[1
,2
,3
]}

Wu, Yangjie ^{[1
]}

机构：

[1] Zhengzhou Univ, Henan Key Lab Chem Biol & Organ Chem, Key Lab Appl Chem Henan Univ, Dept Chem, Zhengzhou 450052, Peoples R China

[2] Huaqiao Univ, Inst Mol Med, Sch Biomed Sci, Xiamen Key Lab Ocean & Gene Drugs, Xiamen 361021, Fujian, Peoples R China

[3] Chinese Educ Minist, Engn Res Ctr Mol Med, Xiamen 361021, Fujian, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 15期

关键词：

DECARBOXYLATIVE ORTHO-ACYLATION; DIRECT ARYLATION; C-8; POSITION; TANDEM SYNTHESIS; ARYL; AZOXYBENZENES; MILD; ALKENYLATION; HETEROCYCLES; ALKENES;

D O I：

10.1021/acs.orglett.6b01746

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient protocol for palladium-catalyzed C8-selective acylation of quinoline N-oxides with alpha-oxocarboxylic acids has been developed. In this approach, N-oxide was utilized as a stepping stone for the remote C-H functionalization. The reaction proceeded efficiently under mild reaction conditions with excellent regioselectivity and broad functional group tolerance.

引用

页码：3722 / 3725

页数：4

共 62 条

[1] Cobalt(III) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer
Barsu, Nagaraju
Sen, Malay
Premkumar, J. Richard
Sundararaju, Basker
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (07) : 1338 - 1341
[2] Synthesis of quinolines, pyridine ligands and biological probes in green media
Bryson, TA
Gibson, JM
Stewart, JJ
Voegtle, H
Tiwari, A
Dawson, JH
Marley, W
Harmon, B
[J]. GREEN CHEMISTRY, 2003, 5 (02) : 177 - 180
[3] Antimalarial Benzylisoquinoline Alkaloid from the Rainforest Tree Doryphora sassafras
Buchanan, Malcolm S.
Davis, Rohan A.
Duffy, Sandra
Avery, Vicky M.
Quinn, Ronald J.
[J]. JOURNAL OF NATURAL PRODUCTS, 2009, 72 (08): : 1541 - 1543
[4] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides
Campeau, LC
Rousseaux, S
Fagnou, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) : 18020 - 18021
[5] Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis
Campeau, Louis-Charles
Stuart, David R.
Leclerc, Jean-Philippe
Bertrand-Laperle, Megan
Villemure, Elisia
Sun, Ho-Yan
Lasserre, Sandrine
Guimond, Nicolas
Lecavallier, Melanie
Fagnou, Keith
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) : 3291 - 3306
[6] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
Chen, Xiao
Engle, Keary M.
Wang, Dong-Hui
Yu, Jin-Quan
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
[7] "One-Pot" Approach to 8-Acylated 2-Quinolinones via Palladium-Catalyzed Regioselective Acylation of Quinoline N-Oxides
Chen, Xiaopei
Cui, Xiuling
Wu, Yangjie
[J]. ORGANIC LETTERS, 2016, 18 (10) : 2411 - 2414
[8] Direct 2-acetoxylation of quinoline N-oxides via copper catalyzed C-H bond activation
Chen, Xuan
Zhu, Chongwei
Cui, Xiuling
Wu, Yangjie
[J]. CHEMICAL COMMUNICATIONS, 2013, 49 (61) : 6900 - 6902
[9] Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes
Cho, Seung Hwan
Hwang, Seung Jun
Chang, Sukbok
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) : 9254 - +
[10] 14-Aminocamptothecins: Their Synthesis, Preclinical Activity, and Potential Use for Cancer Treatment
Duan, Jian-Xin
Cai, Xiaohong
Meng, Fanying
Sun, Jessica D.
Liu, Qian
Jung, Donald
Jiao, Hailong
Matteucci, Jackson
Jung, Brian
Bhupathi, Deepthi
Ahluwalia, Dharmendra
Huang, Heli
Hart, Charles P.
Matteucci, Mark
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (06) : 1715 - 1723

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