Convenient Synthesis of Quinolines from α-2-Nitroaryl Alcohols and Alcohols via a Ruthenium-catalyzed Hydrogen Transfer Strategy

被引：51

作者：

Xie, Feng ^{[1
,2
]}

Zhang, Min ^{[1
]}

Chen, Mengmeng ^{[2
]}

Lv, Wan ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510641, Guangdong, Peoples R China

[2] Jiangnan Univ, Sch Chem & Mat Engn, Wuxi 214122, Peoples R China

来源：

CHEMCATCHEM | 2015年 / 7卷 / 02期

基金：

中国国家自然科学基金;

关键词：

alcohols; annulation; homogeneous catalysis; hydrogen transfer; quinolines; ruthenium; H BOND FUNCTIONALIZATION; SECONDARY ALCOHOLS; BORROWING HYDROGEN; DEHYDROGENATIVE SYNTHESIS; SUBSTITUTED QUINOLINES; IRIDIUM CATALYSTS; AMINE FORMATION; ALKYLATION; DIAMINES; MILD;

D O I：

10.1002/cctc.201402832

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 new and straightforward method for convenient synthesis of quinolines via a ruthenium-catalyzed hydrogen-transfer strategy has been demonstrated. By employing a commercially available ruthenium catalyst system, different alpha-2-nitroaryl alcohols were efficiently converted in combination with a variety of alcohols into various substituted products in reasonable to good yields upon isolation. The synthetic protocol is operationally simple with a broad substrate scope, and there is no need for the use of specialized reducing agents, making it a practical approach for versatile preparation of various quinoline derivatives.

引用

页码：349 / 353

页数：5

共 96 条

[1] Synthesis of Polysubstituted Analogues of the 4-Methyl-2-phenylquinoline [J].

Al-Qahtani, A. A. ;

Al-Turki, T. M. ;

Khan, M. ;

Mousa, A. A. ;

Alkhathlan, H. Z. .

ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (11) :6055-6058

[2] Synthesis, potency, and in vivo profiles of quinoline containing histamine H3 receptor inverse agonists [J].

Altenbach, Robert J. ;

Liu, Huaqing ;

Banfor, Patricia N. ;

Brownian, Kaitlin E. ;

Fox, Gerard B. ;

Fryer, Ryan M. ;

Komater, Victoria A. ;

Krueger, Kathleen M. ;

Marsh, Kennan ;

Miller, Thomas R. ;

Pan, Jia Bao ;

Pan, Liping ;

Sun, Minghua ;

Thiffault, Christine ;

Wetter, Jill ;

Zhao, Chen ;

Zhou, Deliang ;

Esbenshade, Timothy A. ;

Hancock, Arthur A. ;

Cowart, Marlon D. .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (22) :5439-5448

[3]

[Anonymous], 2008, EUR J ORG CHEM

[4] C-H Bond Functionalization in Water Catalyzed by Carboxylato Ruthenium(II) Systems [J].

Arockiam, Percia B. ;

Fischmeister, Cedric ;

Bruneau, Christian ;

Dixneuf, Pierre H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (37) :6629-6632

[5]

Balaraman E, 2013, NAT CHEM, V5, P122, DOI [10.1038/nchem.1536, 10.1038/NCHEM.1536]

[6] Long-range metal-ligand bifunctional catalysis: cyclometallated iridium catalysts for the mild and rapid dehydrogenation of formic acid [J].

Barnard, Jonathan H. ;

Wang, Chao ;

Berry, Neil G. ;

Xiao, Jianliang .

CHEMICAL SCIENCE, 2013, 4 (03) :1234-1244

[7] Catalytic Alkylation of Methyl-N-Heteroaromatics with Alcohols [J].

Blank, Benoit ;

Kempe, Rhett .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (03) :924-+

[8] Selective Iridium-Catalyzed Alkylation of (Hetero) Aromatic Amines and Diamines with Alcohols under Mild Reaction Conditions [J].

Blank, Benoit ;

Michlik, Stefan ;

Kempe, Rhett .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (15) :3790-3799

[9] A Novel Ruthenium-Catalyzed Dehydrogenative Synthesis of 2-Arylquinazolines from 2-Aminoaryl Methanols and Benzonitriles [J].

Chen, Mengmeng ;

Zhang, Min ;

Xiong, Biao ;

Tan, Zhenda ;

Lv, Wan ;

Jiang, Huanfeng .

ORGANIC LETTERS, 2014, 16 (22) :6028-6031

[10] Ruthenium-Catalyzed N-Alkylation for the Synthesis of 2-N-Pyridylmethyl Benzonitriles and an Exploration of Its Synthetic Utility [J].

Chen, Mengmeng ;

Zhang, Min ;

Xie, Feng ;

Wang, Xiaoting ;

Jiang, Huanfeng .

CHEMCATCHEM, 2014, 6 (10) :2993-2997

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