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
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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