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

Chan Sik Cho; Joon Seok Kim; Byoung Ho Oh; Tae Jeong Kim; Sang Chul Shim; Nam Sik Yoon

doi:10.1016/S0040-4020(00)00694-3

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

Chan Sik Cho, Joon Seok Kim, Byoung Ho Oh, Tae Jeong Kim, Sang Chul Shim, Nam Sik Yoon

Department of Applied Chemistry

Kyungpook National University

Research output: Contribution to journal › Article › peer-review

105 Scopus citations

Abstract

Anilines react with allylammonium chlorides in an aqueous medium (H₂O-dioxane) in the presence of a catalytic amount of RuCl₂(PPh₃)₃ together with SnCl₂·2H₂O to give the corresponding quinolines in moderate to good yields. The existence of SnCl₂·2H₂O 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.

Original language	English
Pages (from-to)	7747-7750
Number of pages	4
Journal	Tetrahedron
Volume	56
Issue number	39
DOIs	https://doi.org/10.1016/S0040-4020(00)00694-3
State	Published - 22 Sep 2000

Keywords

Aqueous medium
Catalyst
Cyclization
Quinolines
Ruthenium

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10.1016/S0040-4020(00)00694-3

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

abstract = "Anilines react with allylammonium chlorides in an aqueous medium (H2O-dioxane) in the presence of a catalytic amount of RuCl2(PPh3)3 together with SnCl2·2H2O to give the corresponding quinolines in moderate to good yields. The existence of SnCl2·2H2O 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.",

keywords = "Aqueous medium, Catalyst, Cyclization, Quinolines, Ruthenium",

author = "Cho, {Chan Sik} and Kim, {Joon Seok} and Oh, {Byoung Ho} and Kim, {Tae Jeong} and Shim, {Sang Chul} and Yoon, {Nam Sik}",

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TY - JOUR

T1 - Ruthenium-catalyzed synthesis of quinolines from anilines and allylammonium chlorides in an aqueous medium via amine exchange reaction

AU - Cho, Chan Sik

AU - Kim, Joon Seok

AU - Oh, Byoung Ho

AU - Kim, Tae Jeong

AU - Shim, Sang Chul

AU - Yoon, Nam Sik

PY - 2000/9/22

Y1 - 2000/9/22

N2 - Anilines react with allylammonium chlorides in an aqueous medium (H2O-dioxane) in the presence of a catalytic amount of RuCl2(PPh3)3 together with SnCl2·2H2O to give the corresponding quinolines in moderate to good yields. The existence of SnCl2·2H2O 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.

AB - Anilines react with allylammonium chlorides in an aqueous medium (H2O-dioxane) in the presence of a catalytic amount of RuCl2(PPh3)3 together with SnCl2·2H2O to give the corresponding quinolines in moderate to good yields. The existence of SnCl2·2H2O 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.

KW - Aqueous medium

KW - Catalyst

KW - Cyclization

KW - Quinolines

KW - Ruthenium

UR - http://www.scopus.com/inward/record.url?scp=0034703278&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(00)00694-3

DO - 10.1016/S0040-4020(00)00694-3

M3 - Article

AN - SCOPUS:0034703278

SN - 0040-4020

VL - 56

SP - 7747

EP - 7750

JO - Tetrahedron

JF - Tetrahedron

IS - 39

ER -

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

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Keywords

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