Synthesis of substituted quinolines from N-aryl-N-(2-alkynyl)toluenesulfonamides via FeCl3-mediated intramolecular cyclization and concomitant detosylation

被引：25
作者：
Roy, B. [1 ]
Ansary, Inul [1 ]
Samanta, Srikanta [1 ]
Majumdar, K. C. [1 ]
机构：
[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 38期
关键词：
Sonogashira coupling; N-Aryl-N-(2-alkynyl)toluenesulfonamides; FeCl3; Substituted quinolines; FRIEDLANDER SYNTHESIS; MOLECULAR-IODINE; C BOND; EFFICIENT; ANNULATION; MECHANISM; ARYLATION; ALDEHYDES; KETONES; AMINES;
D O I：
10.1016/j.tetlet.2012.07.047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of substituted quinolines have been synthesized in moderate to good yields (55-81%) from easily available substrates N-aryl-N-(2-alkynyl)toluenesulfonamides via FeCl3-mediated intramolecular cyclization and concomitant detosylation. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5119 / 5122
页数：4
相关论文
共 65 条
[11]   Synthesis and antibacterial evaluation of certain quinolone derivatives [J].
Chen, YL ;
Fang, KC ;
Sheu, JY ;
Hsu, SL ;
Tzeng, CC .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) :2374-2377
[12]  
CHENG CC, 1982, ORG REACTIONS, V28, P37
[13]   A rhodium-catalyzed route for oxidative coupling and cyclization of 2-aminobenzyl alcohol with ketones leading to quinolines [J].
Cho, CS ;
Seok, HJ ;
Shim, SC .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (06) :1219-1222
[14]   Ruthenium-catalyzed synthesis of quinolines from anilines and allylammonium chlorides in an aqueous medium via amine exchange reaction [J].
Cho, CS ;
Kim, JS ;
Oh, BH ;
Kim, TJ ;
Shim, SC ;
Yoon, NS .
TETRAHEDRON, 2000, 56 (39) :7747-7750
[15]  
Combes A., 1888, B CHIM SOC FRANCE, V49, P89
[16]   Iron-catalyzed N-arylations of Amides [J].
Correa, Arkaitz ;
Elmore, Simon ;
Bolm, Carsten .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (12) :3527-3529
[17]   Iron-catalysed carbon-heteroatom and heteroatom-heteroatom bond forming processes [J].
Correa, Arkaitz ;
Mancheno, Olga Garcia ;
Bolm, Carsten .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (06) :1108-1117
[18]   Iron-catalyzed N-arylation of nitrogen nucleophiles [J].
Correa, Arkaitz ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8862-8865
[19]   Synthesis of Diarylamines Catalyzed by Iron Salts [J].
Correa, Arkaitz ;
Carril, Monica ;
Bolm, Carsten .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (35) :10919-10922
[20]   On the mechanism of the Skraup-Doebner-Von Miller quinoline synthesis [J].
Denmark, SE ;
Venkatraman, S .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) :1668-1676
1234567