Metal-free synthesis of highly substituted quinolines under mild conditions

被引：9

作者：

Natarajan, Rakesh ^{[1
]}

Unnikrishnan, Peruparambil A. ^{[1
]}

Radhamani, Sandhya ^{[2
]}

Rappai, John P. ^{[3
]}

Prathapan, Sreedharan ^{[1
]}

机构：

[1] Cochin Univ Sci & Technol, Dept Appl Chem, Kochi 682022, Kerala, India

[2] NSS Coll, Dept Chem, Ottapalam 679103, Palakkad, India

[3] Govt Victoria Coll, Dept Chem, Palakkad 678001, India

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 27-28期

关键词：

Nitrones; Quinolines; Electron deficient acetylenes; Fluorenone; 1,3-Dloplar addition; POLYSUBSTITUTED QUINOLINES; CATALYZED SYNTHESIS; ALCOHOLS; QUINAZOLINE; KETONES;

D O I：

10.1016/j.tetlet.2016.05.091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from easily accessible nitrones and acetylenes, a simple, metal free synthesis of substituted quinolines under mild conditions with high atom efficiency has been developed. Our method is flexible enough to introduce substituents regiospecifically at the 2,3,4,6,8-positions of the quinoline product. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2981 / 2984

页数：4

共 25 条

[1]

Abbiati G., 2009, EUR J ORG CHEM, P1027

[2] Visible-Light-Promoted and One-Pot Synthesis of Phenanthridines and Quinolines from Aldehydes and O-Acyl Hydroxylamine [J].

An, Xiao-De ;

Yu, Shouyun .

ORGANIC LETTERS, 2015, 17 (11) :2692-2695

[3] Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions [J].

Barluenga, Jose ;

Rodriguez, Felix ;

Fananas, Francisco J. .

CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) :1036-1048

[4] Synthesis of enantiopure 4-amino-3-hydroxymethyl-tetrahydroquinolines via an intramolecular nitrone cycloaddition [J].

Broggini, Gianluigi ;

Colombo, Francesco ;

De Marchi, Ivan ;

Galli, Simona ;

Martinelli, Michela ;

Zecchi, Gaetano .

TETRAHEDRON-ASYMMETRY, 2007, 18 (12) :1495-1501

[5] Solid acids: Green alternatives for acid catalysis [J].

Gupta, Princy ;

Paul, Satya .

CATALYSIS TODAY, 2014, 236 :153-170

[6] Synthesis of 3-aryl-2-aminoquinolines: palladium-catalyzed cascade reactions of gem-dibromovinylanilines with tert-butyl isocyanide and arylboronic acids [J].

Hu, Langxi ;

Gui, Weijun ;

Liub, Zichen ;

Jiang, Baishan .

RSC ADVANCES, 2014, 4 (72) :38258-38262

[7] Visible-Light-Promoted Iminyl-Radical Formation from Acyl Oximes: A Unified Approach to Pyridines, Quinolines, and Phenanthridines [J].

Jiang, Heng ;

An, Xiaode ;

Tong, Kun ;

Zheng, Tianyi ;

Zhang, Yan ;

Yu, Shouyun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) :4055-4059

[8] Copper-Catalyzed Synthesis of Substituted Quinolines via C-N Coupling/Condensation from ortho-Acylanilines and Alkenyl Iodides [J].

Kong, Lingkai ;

Zhou, Yuanyuan ;

Huang, He ;

Yang, Yang ;

Liu, Yuanyuan ;

Li, Yanzhong .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02) :1275-1278

[9] Recent progress in the synthesis of quinolines [J].

Kouznetsov, VV ;

Méndez, LYV ;

Gómez, CMM .

CURRENT ORGANIC CHEMISTRY, 2005, 9 (02) :141-161

[10] Ruthenium(II)-Catalyzed Hydrogen Transfer/Annulation Cascade Processes between Alcohols and 2-Nitrobenzaldehydes [J].

Li, Hui-Jing ;

Wang, Chen-Chao ;

Zhu, Shuai ;

Dai, Chun-Yang ;

Wu, Yan-Chao .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (2-3) :583-588

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