Synthetic advances in C(sp2)-H/N-H arylation of pyrazole derivatives through activation/substitution

被引:5
作者
Konwar, Manashjyoti [1 ,2 ]
Hazarika, Roktopol [1 ]
Sarma, Diganta [1 ]
机构
[1] Dibrugarh Univ, Dept Chem, Dibrugarh 786004, Assam, India
[2] Dibru Coll, Dept Chem, Dibrugarh 786003, Assam, India
关键词
N-H Arylation; C-H activation; Heterocyclic compounds; Pyrazole; CATALYZED DIRECT ARYLATION; C-H ARYLATION; REGIOSELECTIVE N-ARYLATION; CROSS-COUPLING REACTIONS; BIOLOGICAL EVALUATION; FUNCTIONALIZATION; ACTIVATION; COMPLEXES; AZOLES; LIGAND;
D O I
10.1016/j.tet.2021.132504
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-heterocyclic compounds and their biological activities are very well known to every researcher. Out of all N-heterocycles, pyrazole is one of the important N-heterocyclic compounds which is a planar five membered aromatic ring with six delocalized is-electrons. As there are various synthetic routes available in literature for the synthesis of pyrazoles, we put our effort for C(sp2)-H arylation of pyrazole derivatives. In this review, we try to describe C(sp2)-H arylation in various positions of pyrazole ring (C-3, C-4, C-5 and N-arylation) through activation or substitution and their medicinal properties associated with it. As the literature reveals, such kind of C(sp2)-H and N-H arylated pyrazoles possess astonishing medicinal properties, they can be firmly incorporated into novel drug molecules which is enough for these mol-ecules to promote themselves as an interesting topic in the present era. (c) 2021 Elsevier Ltd. All rights reserved.
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页数:20
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共 76 条
[1]   Synthesis and fungicidal activity of novel pyrazole derivatives containing 5-Phenyl-2-Furan [J].
Ahmed, Wasim ;
Yan, Xiaojing ;
Hu, Dekun ;
Adnan, Muhammad ;
Tang, Ri-Yuan ;
Cui, Zi-Ning .
BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (19)
[2]   Review: biologically active pyrazole derivatives [J].
Ansari, Anam ;
Ali, Abad ;
Asif, Mohd ;
Shamsuzzaman .
NEW JOURNAL OF CHEMISTRY, 2017, 41 (01) :16-41
[3]   The mechanism of the Wurtz-Fittig reaction [J].
Bachmann, WE ;
Clarke, HT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1927, 49 :2089-2098
[4]   Mild Palladium-Catalyzed Regioselective Direct Arylation of Azoles Promoted by Tetrabutylammonium Acetate [J].
Bellina, Fabio ;
Lessi, Marco ;
Manzini, Chiara .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (25) :5621-5630
[5]   A palladium-catalyzed alkylation/direct arylation synthesis of nitrogen-containing heterocycles [J].
Blaszykowski, Christophe ;
Aktoudianakis, Evangelos ;
Adberico, Dino ;
Bressy, Cyril ;
Hulcoop, David G. ;
Jafarpour, Farnaz ;
Joushaghani, Arash ;
Laleu, Benoit ;
Lautens, Mark .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1888-1897
[6]   Reactivity of 1-(2-bromobenzyl)-4-halopyrazoles in intermolecular and intramolecular Pd-catalysed direct arylations [J].
Brahim, Mariem ;
Ben Ammar, Hamed ;
Soule, Jean-Francois ;
Doucet, Henri .
TETRAHEDRON, 2016, 72 (29) :4312-4320
[7]   Conditions for palladium-catalyzed direct arylations of 4-bromo and 4-iodo N-substituted pyrazoles without C-Br or C-I bond cleavage [J].
Brahim, Mariem ;
Smari, Imen ;
Ben Ammar, Hamed ;
Ben Hassine, Bechir ;
Soule, Jean-Francois ;
Doucet, Henri .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (08) :917-926
[8]   Optimization of a pyrazoloquinolinone class of Chk1 kinase inhibitors [J].
Brnardic, Edward J. ;
Garbaccio, Robert M. ;
Fraley, Mark E. ;
Tasber, Edward S. ;
Steen, Justin T. ;
Arrington, Kenneth L. ;
Dudkin, Vadim Y. ;
Hartman, George D. ;
Stirdivant, Steven M. ;
Drakas, Bob A. ;
Rickert, Keith ;
Walsh, Eileen S. ;
Hamilton, Kelly ;
Buser, Carolyn A. ;
Hardwick, James ;
Tao, Weikang ;
Beek, Stephen C. ;
Mao, Xianzhi ;
Lobell, Robert B. ;
Sepp-Lorenzino, Laura ;
Yan, Youwei ;
Ikuta, Mari ;
Munshi, Sanjeev K. ;
Kuo, Lawrence C. ;
Kreatsoulas, Constantine .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (21) :5989-5994
[9]   Synthesis, optical properties, and characterization of new soluble conjugated poly(p-phenylenevinylene) derivatives constituted of alternating pyrazole and 1,3,4-oxadiazole moieties [J].
Chang, En-Ming ;
Lee, Cheng-Tien ;
Chen, Chun-Yen ;
Wong, Fung Fuh ;
Yeh, Mou-Yung .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2008, 61 (05) :342-349
[10]   Nickel Catalysis Enables Oxidative C(sp2)-H/C(sp2)-H Cross-Coupling Reactions between Two Heteroarenes [J].
Cheng, Yangyang ;
Wu, Yimin ;
Tan, Guangyin ;
You, Jingsong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (40) :12275-12279