Synthesis of Functionalized Quinolines through a Reaction of Amides and Alkynes Promoted by Triflic Anhydride/Pyridine

被引：36

作者：

Li, Lian-Hua ^{[1
]}

Niu, Zhi-Jie ^{[1
]}

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 61期

基金：

中国国家自然科学基金;

关键词：

metal-free; quinoline; regioselectivity; synthesis; triflic anhydride; C-H ACTIVATION; SECONDARY AMIDES; ELECTROPHILIC ACTIVATION; CHEMOSELECTIVE SYNTHESIS; DIRECT TRANSFORMATION; TANDEM REACTION; BOND-CLEAVAGE; ACCESS; COPPER; KETONES;

D O I：

10.1002/chem.201703832

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise, novel and flexible metal-free single step to synthesize functionalized quinolines is reported. Triflic anhydride-mediated (Tf2O) activation of amides is discussed in the presence of pyridine to offer strong electrophiles, thereby showcasing excellent productivity, high regio- and chemoselectivity, and widely tolerable substrates. This approach provides a straightforward and efficient way to construct azaheterocycle structures.

引用

页码：15300 / 15304

页数：5

共 61 条

[1] Synthesis of novel quinoline-2-one based chalcones of potential anti-tumor activity [J].

Abonia, Rodrigo ;

Insuasty, Daniel ;

Castillo, Juan ;

Insuasty, Braulio ;

Quiroga, Jairo ;

Nogueras, Manuel ;

Cobo, Justo .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 57 :29-40

[2] Reversal Agent and Linker Variants of Reversed Chloroquines: Activities against Plasmodium falciparum [J].

Andrews, Simeon ;

Burgess, Steven J. ;

Skaalrud, Deborah ;

Kelly, Jane Xu ;

Peyton, David H. .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (02) :916-919

[3] Highly chemoselective metal-free reduction of tertiary amides [J].

Barbe, Guillaume ;

Charette, Andr B. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) :18-+

[4]

Bechara WS, 2012, NAT CHEM, V4, P228, DOI [10.1038/NCHEM.1268, 10.1038/nchem.1268]

[5] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[6] Practical and highly regio- and stereoselective synthesis of 2-substituted dihydropyridines and piperidines: Application to the synthesis of (-)-coniine [J].

Charette, AB ;

Grenon, M ;

Lemire, A ;

Pourashraf, M ;

Martel, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (47) :11829-11830

[7] Spectroscopic studies of the electrophilic activation of amides with triflic anhydride and pyridine [J].

Charette, AB ;

Grenon, M .

CANADIAN JOURNAL OF CHEMISTRY, 2001, 79 (11) :1694-1703

[8] Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions [J].

Dehli, JR ;

Legros, J ;

Bolm, C .

CHEMICAL COMMUNICATIONS, 2005, (08) :973-986

[9]

Friedlander P., 1882, Chem. Ber, V15, P2572, DOI DOI 10.1002/CBER.188201502219

[10] Quinoline Drug-Heme Interactions and Implications for Antimalarial Cytostatic versus Cytocidal Activities [J].

Gorka, Alexander P. ;

de Dios, Angel ;

Roepe, Paul D. .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (13) :5231-5246

← 1 2 3 4 5 6 7 →