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

被引：28
|
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
收藏
页码：112 / 118
页数：7
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