Ruthenium-catalyzed synthesis of quinolines from anilines and allylammonium chlorides in an aqueous medium via amine exchange reaction

被引：97

作者：

Cho, CS

Kim, JS

Oh, BH

Kim, TJ

Shim, SC ^{[1
]}

Yoon, NS

机构：

[1] Kyungpook Natl Univ, Coll Engn, Dept Ind Chem, Taegu 702701, South Korea

[2] Kyungpook Natl Univ, Coll Engn, Dept Dyeing & Finishing, Taegu 702701, South Korea

来源：

TETRAHEDRON | 2000年 / 56卷 / 39期

关键词：

ruthenium; catalyst; cyclization; quinolines; aqueous medium;

D O I：

10.1016/S0040-4020(00)00694-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Anilines react with allylammonium chlorides in an aqueous medium (H2O-dioxane) in the presence of a catalytic amount of RuCl2(PPh3)(3) together with SnCl2. 2H(2)O to give the corresponding quinolines in moderate to good yields. The existence of SnCl2. 2H(2)O is necessary for the effective formation of quinolines, and a reaction pathway involving amine exchange reaction between anilines and allylammonium chlorides to form an imine is proposed for this catalytic process. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7747 / 7750

页数：4

共 16 条

[1] Ruthenium-catalyzed synthesis of indoles from anilines and trialkanolammonium chlorides in an aqueous medium
Cho, CS
Kim, JH
Shim, SC
TETRAHEDRON LETTERS, 2000, 41 (11) : 1811 - 1814
[2] Ruthenium-catalyzed synthesis of quinolines from anilines and tris(3-hydroxypropyl)amine via amine exchange reaction
Cho, CS
Kim, DT
Kim, TJ
Shim, SC
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (07) : 1026 - 1028
[3] Ruthenium-Catalyzed Synthesis of α-Alkylated Ketones and Quinolines in an Aqueous Medium via a Hydrogen-Borrowing Strategy Using Ketones and Alcohols
Verma, Ashutosh
Hazra, Susanta
Dolui, Pritam
Elias, Anil J.
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (03) : 626 - 633
[4] Ruthenium-catalyzed synthesis of 2-ethyl-3-methylquinolines from anilines and triallylamine
Cho, CS
Oh, BH
Shim, SC
TETRAHEDRON LETTERS, 1999, 40 (08) : 1499 - 1500
[5] An Efficient Synthesis of Benzimidazoles via Palladium-Catalyzed Amine Exchange Reaction from Trialkylamines to o-Phenylenediamine in an Aqueous Medium
Ngoc Thang Tran
Cho, Chan Sik
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (12) : 4188 - 4190
[6] Convenient Synthesis of Quinolines from α-2-Nitroaryl Alcohols and Alcohols via a Ruthenium-catalyzed Hydrogen Transfer Strategy
Xie, Feng
Zhang, Min
Chen, Mengmeng
Lv, Wan
Jiang, Huanfeng
CHEMCATCHEM, 2015, 7 (02) : 349 - 353
[7] Ruthenium-Catalyzed One-Pot Synthesis of Quinolines from Nitroarenes and Trialkylamines
Yang, Huiqiong
Chen, Ru
Deng, Guojun
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (09) : 1725 - 1731
[8] A ruthenium-catalyzed free amine directed (5+1) annulation of anilines with olefins: diverse synthesis of phenanthridine derivatives
Chowdhury, Deepan
Dana, Suman
Mandal, Anup
Baidya, Mahiuddin
CHEMICAL COMMUNICATIONS, 2019, 55 (79) : 11908 - 11911
[9] Ruthenium-catalyzed transfer hydrogenation of aromatic ketones with aminophosphine or bis(phosphino)amine ligands derived from isopropyl substituted anilines
Aydemir, Murat
Baysal, Akin
POLYHEDRON, 2010, 29 (04) : 1219 - 1224
[10] Highly selective synthesis of 1-(silyl)-1-(boryl)ethenes via a ruthenium-catalyzed silylative coupling reaction
Jankowska, M
Marciniec, B
Pietraszuk, C
Cytarska, J
Zaidlewicz, M
TETRAHEDRON LETTERS, 2004, 45 (35) : 6615 - 6618

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