Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones

被引：7
|
作者：
Chen, Lepeng [1 ]
Lv, Ningning [1 ]
Zhen, Qianqian [1 ]
Chen, Zhongyan [1 ]
Ge, Jingyuan [1 ]
Chen, Jiuxi [1 ]
机构：
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 07期
基金：
中国国家自然科学基金;
关键词：
C-H ACTIVATION; ARYLBORONIC ACIDS; ARYL KETONES; NITRILES; CARBOPALLADATION; KETONITRILES; CONDENSATION; IMIDAZOLES; PYRAZOLES; PYRROLES;
D O I：
10.1039/d2qo00036a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Developing efficient methods to accommodate azaheterocycles has been a hotspot field in organic synthesis. Herein, we disclose a facile and expeditious avenue to synthesize 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones via a nickel-catalyzed addition, condensation, and annulation sequence of commercially available dinitriles and boronic acids with hydrazine hydrochlorides. The conversion features a high step economy and good functional group tolerance. The synthetic utility of this methodology is demonstrated by scaled-up reaction and construction of a biologically active triazole biheteroaryl skeleton in a one-pot manner from simple feedstocks.
引用
收藏
页码：1955 / 1959
页数：5
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