Synthesis of Functionalized Pyrazolo[1,5-a]pyridines: [3+2]Cycloaddition of N-Aminopyridines and α,β-Unsaturated Carbonyl Compounds/Alkenes at Room Temperature

被引:23
作者
Ravi, Chitrakar [1 ]
Samanta, Supravat [1 ]
Mohan, Darapaneni Chandra [1 ]
Reddy, N. Naresh Kumar [1 ]
Adimurthy, Subbarayappa [1 ]
机构
[1] Cent Salt & Marine Chem Res Inst, CSIR, Acad Sci & Innovat Res, GB Marg, Bhavnagar 364002, Gujarat, India
来源
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 11期
关键词
N-methylpyrrolidone; chalcones; metal-free; drug intermediates; 3+2] cycloaddition; DOPAMINE-RECEPTOR BINDING; 3+2 CYCLOADDITION; DERIVATIVES; YLIDES; CYCLIZATION; HETEROCYCLES; PYRAZOLES; EFFICACY;
D O I
10.1055/s-0036-1588753
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of functionalized pyrazolo[1,5-a]pyridines through oxidative [3+2] cycloaddition of N-aminopyridines with alpha,beta-unsaturated carbonyl compounds or electron-withdrawing olefins is described. The reactions proceed in N-methylpyrrolidone as the solvent under metal-free conditions at room temperature.
引用
收藏
页码:2513 / 2522
页数:10
相关论文
共 58 条
[1]  
Aboul-Fadl T, 2000, SYNTHESIS-STUTTGART, P1727
[2]   Optimized scale up of 3-pyrimidinylpyrazolo[1,5-a]pyridine via Suzuki coupling; a general method of accessing a range of 3-(hetero)arylpyrazolo[1,5-a]pyridines [J].
Bethel, Paul A. ;
Campbell, Andrew D. ;
Goldberg, Frederick W. ;
Kemmitt, Paul D. ;
Lamont, Gillian M. ;
Suleman, Abid .
TETRAHEDRON, 2012, 68 (27-28) :5434-5444
[3]   Chirospecific and subtype selective dopamine receptor binding of heterocyclic methoxynaphthamide analogs [J].
Bettinetti, L ;
Hübner, H ;
Gmeiner, P .
ARCHIV DER PHARMAZIE, 2005, 338 (5-6) :276-280
[4]   Interactive SAR studies:: Rational discovery of super-potent and highly selective dopamine D3 receptor antagonists and partial agonists [J].
Bettinetti, L ;
Schlotter, K ;
Hübner, H ;
Gmeiner, P .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (21) :4594-4597
[5]   FAUC 213, a highly selective dopamine D4 receptor full antagonist, exhibits atypical antipsychotic properties in behavioural and neurochemical models of schizophrenia [J].
Boeckler, F ;
Russig, H ;
Zhang, WN ;
Löber, S ;
Schetz, J ;
Hübner, H ;
Ferger, B ;
Gmeiner, P ;
Feldon, J .
PSYCHOPHARMACOLOGY, 2004, 175 (01) :7-17
[6]   An Approach of Vulnerability Testing for Third-Party Component Based on Condition and Parameter Mutation [J].
Chen, Jinfu ;
Chen, Jiamei ;
Zhan, Yongzhao ;
Chen, Weihe ;
Huang, Rubing .
SCIENTIFIC WORLD JOURNAL, 2013,
[7]   Silver triflate-copper(II) acetate cooperative catalysis in a cascade reaction for concise synthesis of 2-carbonyl H-pyrazolo[5,1-a]isoquinolines [J].
Chen, Zhiyuan ;
Gao, Liang ;
Ye, Shengqing ;
Ding, Qiuping ;
Wu, Jie .
CHEMICAL COMMUNICATIONS, 2012, 48 (33) :3975-3977
[8]   Efficient Generation of Biologically Active H-Pyrazolo[5,1-a]isoquinolines via Multicomponent Reaction [J].
Chen, Zhiyuan ;
Wu, Jie .
ORGANIC LETTERS, 2010, 12 (21) :4856-4859
[9]   Thermal and Microwave-Assisted Rapid Syntheses of Substituted Imidazo[1,2-a]pyridines Under Solvent- and Catalyst-Free Conditions [J].
Chunavala, Kaushik C. ;
Joshi, Girdhar ;
Suresh, Eringathodi ;
Adimurthy, Subbarayappa .
SYNTHESIS-STUTTGART, 2011, (04) :635-641
[10]   Practical Synthesis of a Cathepsin S Inhibitor: Route Identification, Purification Strategies, and Serendipitous Discovery of a Crystalline Salt form [J].
Deng, Xiaohu ;
Liang, Jimmy T. ;
Peterson, Matthew ;
Rynberg, Raymond ;
Cheung, Eugene ;
Mani, Neelakandha S. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (06) :1940-1947