Palladium-Catalyzed Cyclization Reaction of o-Haloanilines, CO2 and Isocyanides: Access to Quinazoline-2,4(1H,3H)-diones

被引：30

作者：

Zhang, Wen-Zhen ^{[1
]}

Li, Honglin ^{[1
]}

Zeng, Yang ^{[1
]}

Tao, Xueyan ^{[1
]}

Lu, Xiaobing ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Liaoning, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2018年 / 36卷 / 02期

关键词：

carbon dioxide fixation; palladium; isocyanide; nitrogen heterocycles; homogeneous catalysis; CARBON-DIOXIDE INCORPORATION; SOLVENT-FREE SYNTHESIS; CHEMICAL FIXATION; 1,3-DIPOLAR CYCLOADDITION; EFFICIENT SYNTHESIS; CARBOXYLIC-ACIDS; HIGHLY EFFICIENT; DERIVATIVES; DBU; 2-AMINOBENZONITRILE;

D O I：

10.1002/cjoc.201700581

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Quinazoline-2,4(1H,3H)-diones are core structural subunits frequently found in many biologically important compounds. The reaction of 2-aminobenzonitrile and CO2, which was frequently studied, only provided N3-unsubstituted quinazoline-2,4(1H,3H)-dione compounds. Herein we report palladium-catalyzed cyclization reactions of o-haloanilines, CO2 and isocyanides to prepare N3-substituted quinazoline-2,4(1H,3H)-diones. Electron-rich o-bromoanilines participated in the cyclization reaction using Cs2CO3 at high temperature, and electron-deficient o-bromoaniline or o-iodoaniline substrates conducted the reaction using CsF as base to deliver corresponding quinazoline-2,4(1H,3H)-dione products in good yields.

引用

页码：112 / 118

页数：7

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