Copper-Catalyzed 8-Amido Chelation-Induced Remote C-H Amination of Quinolines

被引：87

作者：

Sahoo, Harekrishna ^{[1
]}

Reddy, Mallu Kesava ^{[1
]}

Ramakrishna, Isai ^{[1
]}

Baidya, Mahiuddin ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 05期

关键词：

amination; azo compounds; C-H activation; copper; homogeneous catalysis; BOND ACTIVATION; N-OXIDES; DIRECT ARYLATION; DIRECT ALKYLATION; ALPHA-AMINATION; PALLADIUM; FUNCTIONALIZATION; DERIVATIVES; PYRIDINES; 8-AMINOQUINOLINES;

D O I：

10.1002/chem.201504207

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A copper-catalyzed 8-amide chelation-induced remote C-H amination of quinolines has been developed. This direct amination with readily available azodicarboxylates proceeded with perfect C5-regioselectivity offering amino-substituted 8-aminoquinolines, important bioactive molecular scaffolds, in very high yields (up to 96 %). A single-electron transfer (SET)-mediated mechanism with k(H)/k(D)=1.1 was proposed after trapping of the radical intermediate.

引用

页码：1592 / 1596

页数：5

共 64 条

[31]

Kobayashi S, 1999, CHEM LETT, P307

[32] New diarylamides and diarylureas possessing 8-amino(acetamido) quinoline scaffold: Synthesis, antiproliferative activities against melanoma cell lines, kinase inhibition, and in silico studies [J].

Koh, Eun Jeong ;

El-Gamal, Mohammed I. ;

Oh, Chang-Hyun ;

Lee, So Ha ;

Sim, Taebo ;

Kim, Garam ;

Choi, Hong Seok ;

Hong, Jun Hee ;

Lee, Sang-gi ;

Yoo, Kyung Ho .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 70 :10-21

[33] Rh(NHC)-Catalyzed Direct and Selective Arylation of Quinolines at the 8-Position [J].

Kwak, Jaesung ;

Kim, Min ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (11) :3780-3783

[34] Selective remote C-H sulfonylation of aminoquinolines with arylsulfonyl chlorides via copper catalysis [J].

Liang, Hong-Wen ;

Jiang, Kun ;

Ding, Wei ;

Yuan, Yi ;

Shuai, Li ;

Chen, Ying-Chun ;

Wei, Ye .

CHEMICAL COMMUNICATIONS, 2015, 51 (95) :16928-16931

[35] Direct catalytic asymmetric α-amination of aldehydes [J].

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5656-5657

[36] Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions [J].

Lyons, Thomas W. ;

Sanford, Melanie S. .

CHEMICAL REVIEWS, 2010, 110 (02) :1147-1169

[37] Recent developments in natural product synthesis using metal-catalysed C-H bond functionalisation [J].

McMurray, Lindsay ;

O'Hara, Fionn ;

Gaunt, Matthew J. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1885-1898

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

Michael, Joseph P. .

NATURAL PRODUCT REPORTS, 2008, 25 (01) :166-187

[39] Enantioselective organocatalytic allylic amination [J].

Poulsen, TB ;

Alemparte, C ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11614-11615

[40] 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

← 1 2 3 4 5 6 7 →