Cs2CO3 catalyzed direct aza-Michael addition of azoles to α,β-unsaturated malonates

被引:4
作者
Jiang, Zi-Yu [1 ]
Huang, Zhe-Yao [1 ]
Yang, Hong [1 ]
Zhou, Lin [1 ]
Li, Qing-Han [1 ]
Zhao, Zhi-Gang [1 ]
机构
[1] Southwest Minzu Univ, Coll Chem & Environm, Key Lab Gen Chem, Natl Ethn Affairs Commiss, Chengdu 610041, Peoples R China
基金
中国国家自然科学基金;
关键词
BASIC IONIC LIQUID; N-ARYLATION; ENANTIOSELECTIVE SYNTHESIS; SUBSTITUTED PYRAZOLES; HETEROCYCLES; POTENT; DISCOVERY; BENZOTRIAZOLE; FLUOROARENES; DERIVATIVES;
D O I
10.1039/d2ra02314h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly efficient method for the synthesis of azole derivatives via a direct aza-Michael addition of azoles to alpha,beta-unsaturated malonates using Cs2CO3 as a catalyst, has been successfully developed. A series of azole derivatives have been obtained in up to 94% yield and the reaction could be amplified to gram scale in excellent yield in the presence of 10 mol% of Cs2CO3.
引用
收藏
页码:19265 / 19269
页数:5
相关论文
共 66 条
[1]   2-(1H-Pyrazol-4-yl) acetic acids as CRTh2 antagonists [J].
Andres, Miriam ;
Bravo, Monica ;
Antonia Buil, Maria ;
Calbet, Marta ;
Castro, Jordi ;
Domenech, Teresa ;
Eichhorn, Peter ;
Ferrer, Manel ;
Gomez, Elena ;
Lehner, Martin D. ;
Moreno, Imma ;
Roberts, Richard S. ;
Sevilla, Sara .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (11) :3349-3353
[2]  
[Anonymous], [No title captured]
[3]   Organocatalytic Enantioselective Aza-Michael Reaction of Benzotriazole to ,-Disubstituted Nitroalkenes [J].
Chen, Sheng-Wei ;
Zhang, Gui-Cheng ;
Lou, Qin-Xin ;
Cui, Wei ;
Zhang, Sha-Sha ;
Hu, Wen-Hui ;
Zhao, Jun-Ling .
CHEMCATCHEM, 2015, 7 (13) :1935-1938
[4]   Discovery of potent and orally active 1,4-disubstituted indazoles as novel allosteric glucokinase activators [J].
Cheruvallath, Zacharia S. ;
Gwaltney, Stephen L., II ;
Sabat, Mark ;
Tang, Mingnam ;
Wang, Haixia ;
Jennings, Andy ;
Hosfield, David ;
Lee, Bumsup ;
Wu, Yiqin ;
Halkowycz, Petro ;
Grimshaw, Charles E. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (12) :2678-2682
[5]   N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides [J].
Chevallier, Floris ;
Halauko, Yury S. ;
Pecceu, Christelle ;
Nassar, Ibrahim F. ;
Dam, To Uyen ;
Roisnel, Thierry ;
Matulis, Vadim E. ;
Ivashkevich, Oleg A. ;
Mongin, Florence .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (12) :4671-4684
[6]   Iron-catalyzed N-arylation of nitrogen nucleophiles [J].
Correa, Arkaitz ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8862-8865
[7]   Structure Based Drug Design of Crizotinib (PF-02341066), a Potent and Selective Dual Inhibitor of Mesenchymal-Epithelial Transition Factor (c-MET) Kinase and Anaplastic Lymphoma Kinase (ALK) [J].
Cui, J. Jean ;
Tran-Dube, Michelle ;
Shen, Hong ;
Nambu, Mitchell ;
Kung, Pei-Pei ;
Pairish, Mason ;
Jia, Lei ;
Meng, Jerry ;
Funk, Lee ;
Botrous, Iriny ;
McTigue, Michele ;
Grodsky, Neil ;
Ryan, Kevin ;
Padrique, Ellen ;
Alton, Gordon ;
Timofeevski, Sergei ;
Yamazaki, Shinji ;
Li, Quhua ;
Zou, Helen ;
Christensen, James ;
Mroczkowski, Barbara ;
Bender, Steve ;
Kania, Robert S. ;
Edwards, Martin P. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (18) :6342-6363
[8]   N-Picolinamides as ligands for Ullmann-type C-N coupling reactions [J].
Damkaci, Fehmi ;
Alawaed, Abdulkhaliq ;
Vik, Erik .
TETRAHEDRON LETTERS, 2016, 57 (20) :2197-2200
[9]   Structure-Activity Relationship in Pyrazolo[4,3-c]pyridines, First Inhibitors of PEX14-PEX5 Protein-Protein Interaction with Trypanocidal Activity [J].
Dawidowski, Maciej ;
Kalel, Vishal C. ;
Napolitano, Valeria ;
Fino, Roberto ;
Schorpp, Kenji ;
Emmanouilidis, Leonidas ;
Lenhart, Dominik ;
Ostertag, Michael ;
Kaiser, Marcel ;
Kolonko, Marta ;
Tippler, Bettina ;
Schliebs, Wolfgang ;
Dubin, Grzegorz ;
Maeser, Pascal ;
Tetko, Igor V. ;
Hadian, Kamyar ;
Plettenburg, Oliver ;
Erdmann, Ralf ;
Sattler, Michael ;
Popowicz, Grzegorz M. .
JOURNAL OF MEDICINAL CHEMISTRY, 2020, 63 (02) :847-879
[10]   Enantioselective organocatalytic conjugate addition of N heterocycles to α,β-unsaturated aldehydes [J].
Diner, Peter ;
Nielsen, Martin ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (12) :1983-1987