Base-Promoted Ecofriendly Synthesis of Trisubstituted Pyrazoles from α,β-Alkynyl N-Tosylhydrazones under Metal- and Solvent-Free Conditions

被引:17
作者
Li, Ning [1 ]
Li, Baoguo [1 ]
Chen, Shufeng [1 ]
机构
[1] Inner Mongolia Univ, Dept Chem & Chem Engn, Inner Mongolia Key Lab Fine Organ Synth, Hohhot 010021, Peoples R China
基金
中国国家自然科学基金;
关键词
hydrazones; green chemistry; pyrazoles; cyclizations; ONE-POT SYNTHESIS; FUNCTIONALIZED PYRAZOLES; DERIVATIVES; INHIBITORS; HYDRAZONES; HETEROCYCLES; CYCLIZATION; WATER; DISCOVERY; ARYLATION;
D O I
10.1055/s-0035-1561853
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and green method is described for the synthesis of trisubstituted pyrazoles from ,-alkynyl N-tosylhydrazones under metal- and solvent-free conditions. Notably, only diisopropylamine is required as a promoter, and the reaction can be easily performed at room temperature and on a gram scale.
引用
收藏
页码:1597 / 1601
页数:5
相关论文
共 48 条
[1]   Pim Kinase Inhibitors for the Treatment of Cancer and Possibly More [J].
Abdel-Magid, Ahmed F. .
ACS MEDICINAL CHEMISTRY LETTERS, 2014, 5 (07) :730-731
[2]   Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].
Anderson, Kevin W. ;
Tundel, Rachel E. ;
Ikawa, Takashi ;
Altman, Ryan A. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527
[3]  
[Anonymous], 1984, 13 DIPOLAR CYCLOADDI
[4]  
Barth F, 1999, CURR MED CHEM, V6, P745
[5]   The effect of 1,3-diaryl-[1H]-pyrazole-4-acetamides on glucose utilization in ob/ob mice [J].
Bebernitz, GR ;
Argentieri, G ;
Battle, B ;
Brennan, C ;
Balkan, B ;
Burkey, BF ;
Eckhardt, M ;
Gao, JP ;
Kapa, P ;
Strohschein, RJ ;
Schuster, HF ;
Wilson, M ;
Xu, DD .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (16) :2601-2611
[6]   Discovery of 1-(2,4-Dichlorophenyl)-N-(piperidin-1-yl)-4-((pyrrolidine-1-sulfonamido)methyl)-5-(5-((4-(trifluoromethyl)phenyl)ethynyl)thiophene-2-yl)-1H-pyrazole-3-carboxamide as a Novel Peripherally Restricted Cannabinoid-1 Receptor Antagonist with Significant Weight-Loss Efficacy in Diet-Induced Obese Mice [J].
Chang, Chun-Ping ;
Wu, Chien-Huang ;
Song, Jen-Shin ;
Chou, Ming-Chen ;
Wong, Ying-Chieh ;
Lin, Yinchiu ;
Yeh, Teng-Kuang ;
Sadani, Amit A. ;
Ou, Ming-Hung ;
Chen, Kun-Hung ;
Chen, Pei-Hsuan ;
Kuo, Po-Chu ;
Tseng, Chen-Tso ;
Chang, Kuei-Hua ;
Tseng, Shi-Liang ;
Chao, Yu-Sheng ;
Hung, Ming-Shiu ;
Shia, Kak-Shan .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (24) :9920-9933
[7]   tert-BuOK-Catalyzed condensation of ethyl diazoacetate to aldehydes and palladium-catalyzed 1,2-hydrogen migration for the synthesis of β-ketoesters under solvent-free conditions [J].
Chen, Shufeng ;
Yuan, Fang ;
Zhao, Haiying ;
Li, Baoguo .
RSC ADVANCES, 2013, 3 (31) :12616-12620
[8]   Iron-catalyzed N-arylation of nitrogen nucleophiles [J].
Correa, Arkaitz ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8862-8865
[9]   Synthesis of functionalized tetrasubstituted pyrazolyl heterocycles - A review [J].
Dadiboyena, Sureshbabu ;
Nefzi, Adel .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (11) :5258-5275
[10]   The chemical development of the commercial route to sildenafil: A case history [J].
Dale, DJ ;
Dunn, PJ ;
Golightly, C ;
Hughes, ML ;
Levett, PC ;
Pearce, AK ;
Searle, PM ;
Ward, G ;
Wood, AS .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2000, 4 (01) :17-22