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
相关论文
共 38 条
[1]   Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].
Antilla, JC ;
Baskin, JM ;
Barder, TE ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587
[2]   Microwave-assisted synthesis of N-pyrazole ureas and the p38α inhibitor BIRB 796 for study into accelerated cell ageing [J].
Bagley, Mark C. ;
Davis, Terence ;
Dix, Matthew C. ;
Widdowson, Caroline S. ;
Kipling, David .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (22) :4158-4164
[3]   In situ click chemistry generation of cyclooxygenase-2 inhibitors [J].
Bhardwaj, Atul ;
Kaur, Jatinder ;
Wuest, Melinda ;
Wuest, Frank .
NATURE COMMUNICATIONS, 2017, 8
[4]   Alkyne [3+2] Cycloadditions of Iodosydnones Toward Functionalized 1,3,5-Trisubstituted Pyrazoles [J].
Browne, Duncan L. ;
Taylor, John B. ;
Plant, Andrew ;
Harrity, Joseph P. A. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :984-987
[5]   Organocatalytic Enantioselective Aminoalkylation of 5-Aminopyrazole Derivatives with Cyclic Imines [J].
Carceller-Ferrer, Laura ;
Gonzalez del Campo, Aleix ;
Vila, Carlos ;
Blay, Gonzalo ;
Munoz, M. Carmen ;
Pedro, Jose R. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (48) :7450-7454
[6]   Palladium-Catalyzed Tandem C-C Activation/Cyclization Induced by Carbopalladation of Functionalized Nitriles: Synthesis of Benzo Dipyrromethenes [J].
Chen, Lepeng ;
Gong, Julin ;
Zhang, Yetong ;
Shao, Yinlin ;
Chen, Zhongyan ;
Li, Renhao ;
Chen, Jiuxi .
ORGANIC LETTERS, 2020, 22 (17) :6943-6947
[7]   Metal-Free C-N- and N-N-Bond Formation: Synthesis of 1,2,3-Triazoles from Ketones, N-Tosylhydrazines, and Amines in One Pot [J].
Chen, Zhengkai ;
Yan, Qiangqiang ;
Liu, Zhanxiang ;
Zhang, Yuhong .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) :17635-17639
[8]   α-Iminol Rearrangement Triggered by Pd-Catalyzed C-H Addition to Nitriles Sequences: Synthesis of Functionalized α-Amino Cyclopentanones [J].
Cheng, Na ;
Cui, Shu-Qiang ;
Ma, Qian-Qian ;
Wei, Zhong-Lin ;
Liao, Wei-Wei .
ORGANIC LETTERS, 2021, 23 (03) :1021-1025
[9]   Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles [J].
Dai, Ling ;
Yu, Shuling ;
Lv, Ningning ;
Ye, Xuanzeng ;
Shao, Yinlin ;
Chen, Zhongyan ;
Chen, Jiuxi .
ORGANIC LETTERS, 2021, 23 (15) :5664-5668
[10]   Palladium-catalyzed C-H activation of simple arenes and cascade reaction with nitriles: access to 2,4,5-trisubstituted oxazoles [J].
Dai, Ling ;
Yu, Shuling ;
Shao, Yinlin ;
Li, Renhao ;
Chen, Zhongyan ;
Lv, Ningning ;
Chen, Jiuxi .
CHEMICAL COMMUNICATIONS, 2021, 57 (11) :1376-1379
1234