Cobalt and Copper Co-Catalyzed Three-Component Reactions for the Synthesis of 1,3,4-Trisubstituted Pyrazoles

被引:4
作者
Wei, Daidong [1 ]
Ma, Haojie [1 ]
Zhou, Xiaoqiang [1 ]
Shi, Chong [1 ]
Luo, Xinliang [1 ]
Huang, Guosheng [1 ]
机构
[1] Lanzhou Univ, Dept Chem, State Key Lab Appl Organ Chem, Key Lab Nonferrous Met Chem & Resources Utilizat, Lanzhou, Gansu, Peoples R China
关键词
cobalt; copper; hydrazones; multicomponent reaction; pyrazoles; POTENTIAL ANTIMICROBIAL AGENTS; N BOND FORMATION; 1,3,5-TRISUBSTITUTED PYRAZOLES; BIOLOGICAL EVALUATION; 3+2 CYCLOADDITIONS; ESTROGEN-RECEPTOR; DERIVATIVES; HYDRAZONES; NITROOLEFINS; CYCLOOXYGENASE-2;
D O I
10.1002/slct.201700987
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel cobalt and copper co-catalyzed for exclusive synthesis of 1,3,4-trisubstituted pyrazoles via a one-pot reaction of hydrazones with nitromethane and aldehydes has been reported. Proper conditions without additional oxidants, broad substrate scope and easily obtained starting materials make this protocol promising and practical.
引用
收藏
页码:6231 / 6234
页数:4
相关论文
共 50 条
[1]  
Abu T. B., 2012, J MED CHEM, V55, P961
[2]  
[Anonymous], TOP HETEROCYCL CHEM
[3]   Efficient tautomerization hydrazone-azomethine imine under microwave irradiation.: Synthesis of [4,3′] and [5,3′]bipyrazoles [J].
Arrieta, A ;
Carrillo, JR ;
Cossío, FP ;
Díaz-Ortiz, A ;
Gómez-Escalonilla, MJ ;
de la Hoz, A ;
Langa, F ;
Moreno, A .
TETRAHEDRON, 1998, 54 (43) :13167-13180
[4]   NONPEPTIDE ANGIOTENSIN-II ANTAGONISTS DERIVED FROM 1H-PYRAZOLE-5-CARBOXYLATES AND 4-ARYL-1H-IMIDAZOLE-5-CARBOXYLATES [J].
ASHTON, WT ;
HUTCHINS, SM ;
GREENLEE, WJ ;
DOSS, GA ;
CHANG, RSL ;
LOTTI, VJ ;
FAUST, KA ;
CHEN, TB ;
ZINGARO, GJ ;
KIVLIGHN, SD ;
SIEGL, PKS .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (23) :3595-3605
[5]   Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents [J].
Bekhit, AA ;
Abdel-Aziem, T .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (08) :1935-1945
[6]   Correlation of spectroscopically determined ligand donor strength and nucleophilicity of substituted pyrazoles [J].
Bernhammer, Jan Christopher ;
Han Vinh Huynh .
DALTON TRANSACTIONS, 2012, 41 (28) :8600-8608
[7]   Divergent C-H Functionalizations Directed by Sulfonamide Pharmacophores: Late-Stage Diversification as a Tool for Drug Discovery [J].
Dai, Hui-Xiong ;
Stepan, Antonia F. ;
Plummer, Mark S. ;
Zhang, Yang-Hui ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (18) :7222-7228
[8]   Base-mediated reaction of hydrazones and nitroolefins with a reversed regio selectivity: A novel synthesis of 1,3,4-trisubstituted pyrazoles [J].
Deng, Xiaohu ;
Mani, Neelakandha S. .
ORGANIC LETTERS, 2008, 10 (06) :1307-1310
[9]   Reaction of N-monosubstituted hydrazones with nitroolefins:: A novel regioselective pyrazole synthesis [J].
Deng, Xiaohu ;
Mani, Neelakandha S. .
ORGANIC LETTERS, 2006, 8 (16) :3505-3508
[10]   N-(4-Cyanotetrahydro-2H-pyran-4-yl) and N-(1-Cyanocyclohexyl) Derivatives of 1,5-Diarylpyrazole-3-carboxamides Showing High Affinity for 18 kDa Translocator Protein and/or Cannabinoid Receptors [J].
Donohue, Sean R. ;
Dannals, Robert F. ;
Halldin, Christer ;
Pike, Victor W. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (08) :2961-2970