Recent Progress in Synthesis of Polysubstituted Pyrazoles
- Corresponding author: Ma Aijun, maaijun@wyu.edu.cn Xu Xuetao, xuetaoxu@wyu.edu.cn
Citation:
Wang Shaohua, Zhang Banghong, Chen Jie, Zheng Yingying, Feng Na, Ma Aijun, Xu Xuetao, Abdullah M. Asiri. Recent Progress in Synthesis of Polysubstituted Pyrazoles[J]. Chinese Journal of Organic Chemistry,
;2020, 40(1): 15-27.
doi:
10.6023/cjoc201906007
(a) Dedeian, K.; Shi, J.; Shepherd, N.; Forsythe, E.; Morton, D. C. Inorg. Chem. 2005, 44, 4445.
(b) Chang, S. Y.; Chen, J. L.; Chi, Y.; Cheng, Y. M.; Lee, G. H.; Jiang, C. M.; Chou, P. T. Inorg. Chem. 2007, 46, 11202.
(c) Cavero, E.; Uriel, S.; Romero, P.; Serrano, J. L.; Giménez, R. J. Am. Chem. Soc. 2007, 129, 11608.
(d) Ye, C.; Gard, G. L.; Winter, R. W.; Syvret, R. G.; Twamley, B.; Shreeve, J. M. Org Lett. 2007, 9, 3841.
(e) Yang, L.; Okuda, F.; Kobayashi, K.; Nozaki, K.; Tanabe, Y.; Ishii, Y.; Haga, M. Inorg Chem. 2008, 47, 7154.
(f) Seltzman, H. H. Drug Dev. Res. 2009, 70. 601.
(g) Dai, H. X.; Stepan, A. F.; Plummer, M. S.; Zhang, Y. H.; Yu, J. Q. J. Am. Chem. Soc. 2011, 133, 7222.
(h) Jones, L. H.; Allan, G.; Corbau, R.; Middleton, D. S.; Mowbray, C. E.; Newman, S. D.; Phillips, C.; Webster, R.; Westby, M. Chem. Biol. Drug Des. 2011, 77, 393.
(i) Kumar, V.; Kaur, K.; Gupta, G. K.; Sharma, A. K. Eur. J. Med. Chem. 2013, 69, 735.
(a) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159.
(b) Rosiak, A.; Hoenke, C.; Christoffers, J. Eur. J. Org. Chem. 2007, 26, 4376.
(c) Fustero, S.; Sanchez-Rosello, M.; Barrio, P.; Simon-Fuentes, A. Chem. Rev. 2011, 111, 6984.
(d) Hu, J.; Cheng, Y.; Yang, Y.; Rao, Y. Chem. Commun. 2011, 47, 10133.
(e) Lominac, W. J.; D'Angelo, M. L.; Smith, M. D.; Ollison, D. A.; Hanna, J. J. M. Tetrahedron Lett. 2012, 53, 906.
(f) Peng, J.; Xie, Z.; Chen, M.; Wang, J.; Zhu. Q. Org Lett. 2014, 16, 4702.
(g) Tang, M.; Kong, Y.; Chu, B.; Feng, D. Adv. Synth. Catal. 2016, 358, 926.
Geng, R.; Zhao, Y.; Li, Y.; Liu, X.; Wang, M. Chin. J. Org. Chem. 2019, 39, 3574(in Chinese).
Zhong, L.; Jiang, T.; Zhang, F.; Fu, Q.; Liu, X.; Xu, T.; Ding, C.; Chen, J.; Yuan, J.; Tan, C. Chin. J. Org. Chem. 2019, 39, 2655(in Chinese).
Gong, C. C.; Tan, H. Y.; Zhang, Q. Chin. J. Org. Chem. 2018, 38, 3086(in Chinese).
He, B.; Wang, D. W.; Yang, W. C.; Chen, Q.; Yang, G. F. Chin. J. Org. Chem. 2017, 37, 2895(in Chinese).
Zhong, Y. Y.; Yu, L. J.; He, Q. Y.; Zhu, Q. Y.; Zhang, C. G.; Cui, X. P.; Zheng, J. X.; Zhao, S. Q. ACS Appl. Mater. Inter. 2019, 11, 32769.
doi: 10.1021/acsami.9b11754
Sun, N. B.; Shen, Z. H.; Zhai, Z. W.; Han, L.; Weng, J. Q.; Tan, C. X.; Liu, X. H. Chin. J. Org. Chem. 2017, 37, 2705(in Chinese).
Shi, Y. J.; Zhou, Q.; Wang, Y.; Qian, H. W.; Ye, L. Y.; Feng, X.; Chen, H.; Li, Y. T.; Dai, H.; Wei, Z. H.; Wu, J. M. Chin. J. Org. Chem. 2018, 38, 2450(in Chinese).
Zhu, Q.; Yang, Y.; Lao, Z.; Zhong, Y.; Zhang, B.; Cui, X.; O'Neill, P.; Hong, D.; Zhang, K.; Zhao, S. Pest. Manage. Sci. 2019, DOI:10.1002/ps.5559.
doi: 10.1002/ps.5559
Abd El Razik, H. A.; Badr, M. H.; Atta, A. H.; Mouneir, S. M.; Abu-Serie, M. M. Arch. Pharm. 2017, 350, e1700026.
doi: 10.1002/ardp.201700026
Schmidt, A.; Dreger, A. Curr. Org. Chem. 2011, 15, 1423.
doi: 10.2174/138527211795378263
(a) Bekhit, A. A.; Abdel-Aziem, T. Bioorg. Med. Chem. 2004, 12, 1935.
(b) Selvam, C.; Jachak, S. M.; Thilagavathi, R.; Chakraborti, A. K. Bioorg. Med. Chem. Lett. 2005, 15, 1793.
(c) El-Sayed, M. A. A.; Abdel-Aziz, N. I.; Abdel-Aziz, A. A. M.; El-Azab, A. S.; ElTahir, K. E. H. Bioorg. Med. Chem. 2012, 20, 3306.
Tanitame, A.; Oyamada, Y.; Ofuji, K.; Fujimoto, M.; Iwai, N.; Hiyama, Y.; Suzuki, K.; Ito, H.; Terauchi, H.; Kawasaki, M.; Nagai, K.; Wachi, M.; Yamagishi, J. J. Med. Chem. 2004, 47, 3693.
doi: 10.1021/jm030394f
Bhosle, M. R.; Mali, J. R.; Pal, S.; Srivastava, A. K.; Mane, R. A. Bioorg. Med. Chem. Lett. 2014, 24, 2651.
doi: 10.1016/j.bmcl.2014.04.064
Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347.
doi: 10.1021/jm960803q
Cox, S. R.; Lesman, S. P.; Boucher, J. F.; Krautmann, M. J.; Hummel, B. D.; Savides, M.; Marsh, S.; Fielde, A.; Stegemann, M. R. J. Vet. Pharmacol. Ther. 2010, 33, 461.
doi: 10.1111/j.1365-2885.2010.01165.x
Zhang, D.; Raghavan, N.; Chen, S. Y.; Zhang, H.; Quan, M.; Lecureux, L.; Patrone, L. M.; Lam, P. Y. S.; Bonacorsi, S. J.; Knabb, R. M.; Skiles, G. S.; He, K. Drug Metab. Dispos. 2008, 36, 303.
doi: 10.1124/dmd.107.018416
Lange, J. H. M.; van Stuivenberg, H. H.; Coolen, H. K. A. C.; Adolfs, T. J. P.; McCreary, A. C.; Keizer, H. G.; Wals, H. C.; Veerman, W.; Borst, A. J. M.; de Looff, W.; Verveer, P. C.; Kruse, C. G. J. Med. Chem. 2005, 48, 1823.
doi: 10.1021/jm040843r
Graneto, M. J.; Kurumbail, R. G.; Vazquez, M. L.; Shieh, H. S.; Pawlitz, J. L.; Williams, J. M.; Stallings, W. C.; Geng, L.; Naraian, A. S.; Koszyk, F. J.; Stealey, M. A.; Xu, X. D.; Weier, R. M.; Hanson, G. J.; Mourey, R. J.; Compton, R. P.; Mnich, S. J.; Anderson, G. D.; Monahan, J. B.; Devraj, R. J. Med. Chem. 2007, 50, 5712.
doi: 10.1021/jm0611915
Barth, F.; Rinaldi-Carmona, M. Curr. Med. Chem. 1999, 6, 745.
Cox, B. D.; Prosser, A. R.; Sun, Y.; Li, Z.; Lee, S.; Huang, M. B.; Bond, V. C.; Snyder, J. P.; Krystal, M.; Wilson, L. J.; Liotta, D. C. ACS Med. Chem. Lett. 2015, 6, 753.
doi: 10.1021/acsmedchemlett.5b00036
Labroli, M. A.; Dwyer, M. P.; Poker, C.; Keertikar, K. M.; Rossman, R.; Guzi, T. J. Tetrahedron Lett. 2016, 57, 2601.
doi: 10.1016/j.tetlet.2016.04.102
Knorr, L. Ber. Dtsch. Chem. Ges. 1883, 16, 2593.
doi: 10.1002/cber.188301602193
Singh, S. P.; Kumar, D.; Batra, H.; Naithani, R.; Rozas, I.; Elguero, J. Can. J. Chem. 2000, 78, 1109.
doi: 10.1139/v00-104
Oliveira, D. H.; Aquino, T. B.; Nascimento, J. E. R.; Perin, G.; Jacob, R. G.; Alves, D. Adv. Synth. Catal. 2015, 357, 4041.
doi: 10.1002/adsc.201500625
Zora, M.; Demirci, D.; Kivrak, A.; Kelgokmen, Y. Tetrahedron Lett. 2016, 57, 993.
doi: 10.1016/j.tetlet.2016.01.071
Sun, P.; Yang, D.; Wei, W.; Sun, X.; Zhang, W.; Zhang, H.; Wang, Y.; Wang, H. Tetrahedron 2017, 73, 2022.
doi: 10.1016/j.tet.2017.02.046
Kalita, S. J.; Bayan, R.; Devi, J.; Brahma, S.; Mecadon, H.; Deka, D. C. Tetrahedron Lett. 2017, 58, 566.
doi: 10.1016/j.tetlet.2016.12.084
Zhang, H.; Wei, Q.; Zhu, G.; Qu, J.; Wang, B. Tetrahedron Lett. 2016, 57, 2633.
doi: 10.1016/j.tetlet.2016.05.020
Markovic, V.; Joksovic, M. D. Green Chem. 2015, 17, 842.
doi: 10.1039/C4GC02028F
Vekariya, R. H.; Patel, K. D.; Patel, H. D. Res. Chem. Intermed. 2016, 42, 4683.
doi: 10.1007/s11164-015-2308-7
Saha, A.; Payra, S.; Banerjee, S. Green Chem. 2015, 17, 2859.
doi: 10.1039/C4GC02420F
Sun, A.; Ye, J. H.; Yu, H.; Zhang, W.; Wang, X. Tetrahedron Lett. 2014, 55, 889.
doi: 10.1016/j.tetlet.2013.12.045
Kong, Y.; Tang, M.; Wang, Y. Org. Lett. 2014, 16, 576.
doi: 10.1021/ol403447g
Tang, M.; Wang, Y.; Wang, H.; Kong, Y. Synthesis 2016, 48, 3065.
doi: 10.1055/s-0035-1561646
Senadi, G. C.; Hu, W. P.; Lu, T. Y.; Garkhedkar, A. M.; Vandavasi, J. K.; Wang, J. J. Org Lett. 2015, 17, 1521.
doi: 10.1021/acs.orglett.5b00398
Alizadeh, A.; Moafi, L.; Zhu, L. G. Synlett 2016, 27, 595.
Shi, C.; Ma, C.; Ma, H.; Zhou, X.; Cao, J.; Fan, Y.; Huang, G. Tetrahedron 2016, 72, 4055.
doi: 10.1016/j.tet.2016.05.034
Yu, Y.; Huang, W.; Chen, Y.; Gao, B.; Wu, W.; Jiang, H. Green Chem. 2016, 18, 6445.
doi: 10.1039/C6GC02776H
Mukherjee, S.; Kundu, A.; Pramanik, A. Tetrahedron Lett. 2016, 57, 2103.
doi: 10.1016/j.tetlet.2016.04.002
Zhang, G.; Ni, H.; Chen, W.; Shao, J.; Liu, H.; Chen, B.; Yu, Y. Org. Lett. 2013, 15, 5967.
doi: 10.1021/ol402810f
Zhang, J.; Chen, W.; Huang, D.; Zeng, X.; Wang, X.; Hu, Y. Tetrahedron Lett. 2017, 58, 4133.
doi: 10.1016/j.tetlet.2017.09.050
Kumar, R.; Nair, D.; Namboothiri, I. N. N. Tetrahedron 2014, 70, 179.
Nair, D.; Pavashe, P.; Katiyar, S.; Namboothiri, I. N. N. Tetrahedron Lett. 2016, 57, 3146.
doi: 10.1016/j.tetlet.2016.06.020
Ahamad, S.; Gupta, A. K.; Kant, R.; Mohanan, K. Org. Biomol. Chem. 2015, 13, 1492.
doi: 10.1039/C4OB02365J
Shao, Y.; Tong, J.; Zhao, Y.; Zheng, H.; Ma, L.; Ma, M.; Wan, X. Org. Biomol. Chem. 2016, 14, 8486.
doi: 10.1039/C6OB01522K
(a) Yuan, B.; Zhang, F.; Li, Z.; Yang, S.; Yan, R. Org. Lett. 2016, 18, 5928.
(b) Unnava, R.; Saikia A. K. ChemistrySlect 2016, 1, 1816.
Yadav, S.; Rai, P.; Srivastava, M.; Singh, J.; Tiwari, K. P.; Singh, J. Tetrahedron Lett. 2015, 56, 5831.
doi: 10.1016/j.tetlet.2015.07.039
Cheng, J.; Li, W.; Duan, Y.; Cheng, Y.; Yu, S.; Zhu, C. Org. Lett. 2017, 19, 214.
doi: 10.1021/acs.orglett.6b03497
Dhage, Y. D.; Daimon, H.; Peng, C.; Kusakabe, T.; Takahashi, K.; Kanno, Y.; Inouye, Y.; Kato, K. Org. Biomol. Chem. 2014, 12, 8619.
doi: 10.1039/C4OB01576B
Li, D. Y.; Mao, X. F.; Chen, H. J.; Chen, G. R.; Liu, P. N. Org. Lett. 2014, 16, 3476.
doi: 10.1021/ol501402p
Tu, Y.; Zhang, Z.; Wang, T.; Ke, J.; Zhao, J. Org. Lett. 2017, 19, 3466.
doi: 10.1021/acs.orglett.7b01447
Zhu, Y.; Lu, W. T.; Sun, H. C.; Zhan, Z. P. Org. Lett. 2013, 15, 4146.
doi: 10.1021/ol401818m
Yang, Y.; Hu, Z. L.; Li, R. H.; Chen, Y. H.; Zhan, Z. P. Org. Biomol. Chem. 2018, 16, 197.
doi: 10.1039/C7OB02576A
Schmitt, D. C.; Taylor, A. P.; Flick, A. C.; Kyne, R. E. Org. Lett. 2015, 17, 1405.
doi: 10.1021/acs.orglett.5b00266
Chen, B.; Zhu, C.; Tang, Y.; Ma, S. Chem. Commun. 2014, 50, 7677.
doi: 10.1039/c4cc02856b
Tang, X.; Huang, L.; Yang, J.; Xu, Y.; Wu, W.; Jiang, H. Chem. Commun. 2014, 50, 14793.
doi: 10.1039/C4CC06747A
Mamaghani, M.; Hossein, R.; Shirini, F.; Tabatabaeian, K.; Rassa, M. Med. Chem. Res. 2015, 24, 1916.
doi: 10.1007/s00044-014-1271-y
Karnakar, K.; Ramesh, K.; Reddy, K. H. V.; Anil Kumar, B. S. P.; Nanubonula, J. B.; Nageswar, Y. V. D. New J. Chem. 2015, 39, 8978.
doi: 10.1039/C5NJ01448D
Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
Yuyang Xu , Ruying Yang , Yanzhe Zhang , Yandong Liu , Keyi Li , Zehui Wei . Research Progress of Aflatoxins Removal by Modern Optical Methods. University Chemistry, 2024, 39(11): 174-181. doi: 10.12461/PKU.DXHX202402064
Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . 二维共价有机框架作为光催化剂在有机合成中的研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-. doi: 10.1016/j.actphy.2025.100086
Zongfei YANG , Xiaosen ZHAO , Jing LI , Wenchang ZHUANG . Research advances in heteropolyoxoniobates. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 465-480. doi: 10.11862/CJIC.20230306
Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
Wenli FENG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress on ultralong room temperature phosphorescent carbon dots. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 833-846. doi: 10.11862/CJIC.20240308
Xinxin JING , Weiduo WANG , Hesu MO , Peng TAN , Zhigang CHEN , Zhengying WU , Linbing SUN . Research progress on photothermal materials and their application in solar desalination. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1033-1064. doi: 10.11862/CJIC.20230371
Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
Bin HE , Hao ZHANG , Lin XU , Yanghe LIU , Feifan LANG , Jiandong PANG . Recent progress in multicomponent zirconium?based metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2041-2062. doi: 10.11862/CJIC.20240161
Yu Guo , Zhiwei Huang , Yuqing Hu , Junzhe Li , Jie Xu . 钠离子电池中铁基异质结构负极材料的最新研究进展. Acta Physico-Chimica Sinica, 2025, 41(3): 2311015-. doi: 10.3866/PKU.WHXB202311015
Yuhang Zhang , Weiwei Zhao , Hongwei Liu , Junpeng Lü . 基于低维材料的自供电光电探测器研究进展. Acta Physico-Chimica Sinica, 2025, 41(3): 2310004-. doi: 10.3866/PKU.WHXB202310004
Tingting XU , Wenjing ZHANG , Yongbo SONG . Research advances of atomic precision coinage metal nanoclusters in tumor therapy. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2275-2285. doi: 10.11862/CJIC.20240229
Yongjie ZHANG , Bintong HUANG , Yueming ZHAI . Research progress of formation mechanism and characterization techniques of protein corona on the surface of nanoparticles. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2318-2334. doi: 10.11862/CJIC.20240247