One-pot, three-component synthesis of dialkyl 1,2-dihydroquinoline-2,3-dicarboxylates from triphenylphosphine, acetylenic esters, and amide derivatives of 2-aminobenzaldehyde in aqueous acetone

被引：55

作者：

Ramazani, A

Ahmadi, E

Kazemizadeh, AR

Dolatyari, L

Noshiranzadeh, N

Eskandari, I

Souldozi, A

机构：

[1] Zanjan Univ, Dept Chem, Zanjan, Iran

[2] Zanjan Islamic Azad Univ, Dept Chem, Zanjan, Iran

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2005年 / 180卷 / 11期

关键词：

2 '-formylacetanilide; 2 '-formylbenzanilide; acetylenic ester; intramolecular Wittig reaction; triphenylphosphine;

D O I：

10.1080/104265090921137

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates by amide derivatives of 2-aminobenzaldehyde in the mixture of acetone-water (3:1) leads to vinyltriphenylphosphonium salts, which undergo a Michael addition reaction with a conjugate base to produce the corresponding stabilized phosphorus ylides. An intramolecular Wittig reaction of the stabilized phosphorus ylide group with the aldehyde group leads to the corresponding dialkyl 1,2-diltydroquinoline-2,3-dicarboxylates.

引用

页码：2419 / 2422

页数：4

共 6 条

[1]

Cadogan J. I. G., 1979, Organophosphorus Reagents in Organic Synthesis

[2]

Ramazani A, 2004, Z KRIST-NEW CRYST ST, V219, P243

[3] Conversion of in situ generated stabilized phosphorus ylides to chromene derivatives in solvent-free conditions [J].