Electrochemically Enabled Double C-H Activation of Amides: Chemoselective Synthesis of Polycyclic Isoquinolinones

被引：64

作者：

Wang, Zi-Qiang ^{[1
]}

Hou, Cheng ^{[1
]}

Zhong, Yuan -Fang ^{[1
]}

Lu, Yu-Xuan ^{[1
]}

Mo, Zu-Yu ^{[1
]}

Pan, Ying-Ming ^{[1
]}

Tang, Hai-Tao ^{[1
]}

机构：

[1] Guangxi Normal Univ, State Key Lab Chem & Mol Engn Med Resources, Sch Chem & Pharmaceut Sci, Guilin 541004, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 24期

基金：

中国国家自然科学基金;

关键词：

BENZAMIDES; OXIDANT; METAL; ANNULATION; DISCOVERY; CATALYSIS; EFFICIENT; ACCESS;

D O I：

10.1021/acs.orglett.9b03682

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed an electrochemically enabled dehydrogenative annulation reaction of amides and alkynes for the synthesis of antitumor polycyclic isoquinolinones through a double C-H activation route. No external oxidant is required in this reaction, and electricity is used for Ru catalyst circulation. The most remarkable feature of this reaction is the effective improvement of product regioselectivity under mild electrolytic conditions in comparison with previously set strong oxidant conditions.

引用

页码：9841 / 9845

页数：5

共 61 条

[1] Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds
Ackermann, Lutz
Lygin, Alexander V.
Hofmann, Nora
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) : 6379 - 6382
[2] Soluble polymer-supported catalysts containing azo dyes
Bergbreiter, DE
Osburn, PL
Li, CM
[J]. ORGANIC LETTERS, 2002, 4 (05) : 737 - 740
[3] Breit B., 2019, ANGEW CHEM, V58, P1
[4] Analysis of the reactions used for the preparation of drug candidate molecules
Carey, John S.
Laffan, David
Thomson, Colin
Williams, Mike T.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) : 2337 - 2347
[5] Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes
Cheung, Chi Wai
Ma, Jun-An
Hu, Xile
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (22) : 6789 - 6792
[6] Regiodivergent Iridium(III)-Catalyzed Diamination of Alkenyl Amides with Secondary Amines: Complementary Access to γ- or δ-Lactams
Conway, John H., Jr.
Rovis, Tomislav
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (01) : 135 - 138
[7] Visible-Light-Mediated Synthesis of Amidyl Radicals: Transition Metal-Free Hydroamination and N-Arylation Reactions
Davies, Jacob
Svejstrup, Thomas D.
Reina, Daniel Fernandez
Sheikh, Nadeem S.
Leonori, Daniele
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (26) : 8092 - 8095
[8] Nonclassical Routes for Amide Bond Formation
de Figueiredo, Renata Marcia
Suppo, Jean-Simon
Campagne, Jean-Marc
[J]. CHEMICAL REVIEWS, 2016, 116 (19) : 12029 - 12122
[9] Redox catalysis in organic electrosynthesis: basic principles and recent developments
Francke, Robert
Little, R. Daniel
[J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) : 2492 - 2521
[10] A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases
Ghose, AK
Viswanadhan, VN
Wendoloski, JJ
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (01): : 55 - 68

← 1 2 3 4 5 6 7 →