p-toluenesulfonic acid-catalyzed synthesis of polysubstituted quinolines via Friedlander reaction under ball-milling conditions at room temperature and theoretical study on the mechanism using a density functional theory method

被引：19

作者：

Javanshir, Shahrzad ^{[1
]}

Sharifi, Shahin ^{[1
]}

Maleki, Ali ^{[1
]}

Sohrabi, Beheshteh ^{[1
]}

Kiasadegh, Mehdi ^{[1
]}

机构：

[1] Iran Univ Sci & Technol, Dept Chem, Tehran 1684613114, Iran

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2014年 / 27卷 / 07期

关键词：

ball-milling; density function theory; Friedlander reaction; p-toluenesulfonic acid; quinolines; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; HIGHLY EFFICIENT; CARBONYL-COMPOUNDS; DERIVATIVES; ENERGY; QUINAZOLINE; PROTOCOL; KETONES;

D O I：

10.1002/poc.3305

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of polysubstituted quinolines was accomplished through Friedlander annulation between 2-aminoaryl ketones and different active methylene compounds at room temperature using ball-milling technique in the presence of p-toluenesulfonic acid. The mechanism of the reaction investigated by density functional theory-based modeling is also reported. This study aims at giving insight into the mechanism of the Friedlander reaction in the presence of acid catalysts. Copyright (c) 2014 John Wiley & Sons, Ltd.

引用

页码：589 / 596

页数：8