综述与进展

多取代吡唑合成最新研究进展

  • 王少华 ,
  • 张帮红 ,
  • 陈洁 ,
  • 郑莹莹 ,
  • 冯娜 ,
  • 马爱军 ,
  • 徐学涛 ,
  • Abdullah M. Asiri
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  • a 五邑大学生物科技与大健康学院 广东江门 529020;
    b 江门市大健康国际创新研究院 广东江门 529020;
    c 兰州大学药学院 兰州 730000;
    d Faculty of Science, King Abdulaziz University, Jeddah 999088

收稿日期: 2019-06-06

  修回日期: 2019-09-01

  网络出版日期: 2019-09-05

基金资助

国家自然科学基金(Nos.21472077,21772071)、广东省教育厅基金(Nos.2017KTSCX185,2017KSYS010,2016KCXTD005)、五邑大学高层次人才科研启动(Nos.2018AL002,2018AL003)资助项目.

Recent Progress in Synthesis of Polysubstituted Pyrazoles

  • Wang Shaohua ,
  • Zhang Banghong ,
  • Chen Jie ,
  • Zheng Yingying ,
  • Feng Na ,
  • Ma Aijun ,
  • Xu Xuetao ,
  • Abdullah M. Asiri
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  • a School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020;
    b International Healthcare Innovation Institute, Jiangmen, Guangdong 529000;
    c School of Pharmacy, Lanzhou University, Lanzhou 730000;
    d Faculty of Science, King Abdulaziz University, Jeddah 999088

Received date: 2019-06-06

  Revised date: 2019-09-01

  Online published: 2019-09-05

Supported by

Project supported by the the National Natural Science Foundation of China (Nos. 21472077, 21772071), the Department of Education of Guangdong Province (Nos. 2017KTSCX185, 2017KSYS010, 2016KCXTD005), and the High-level Talent Research Start-up Project of Wuyi University (Nos. 2018AL002, 2018AL003).

摘要

吡唑是一类重要的五元含氮杂环化合物,广泛存在于许多天然产物、生物活性分子和药物分子中,而且是一类重要的有机合成中间体.因此,近年来吡唑及其衍生物的合成引起了科学家们的极大兴趣,并得以迅速发展.对近年来多取代吡唑的合成新方法进行了综述,以期对相关领域的研究起到一定的辅助与推动作用.

关键词: 吡唑; 合成; 研究进展

本文引用格式

王少华 , 张帮红 , 陈洁 , 郑莹莹 , 冯娜 , 马爱军 , 徐学涛 , Abdullah M. Asiri . 多取代吡唑合成最新研究进展[J]. 有机化学, 2020 , 40(1) : 15 -27 . DOI: 10.6023/cjoc201906007

Abstract

Pyrazole, an important class of nitrogen-containing five-member hetrocyclic compounds, widely exists in natural products, bio-active molecules and drugs, and it is also a valuable intermediate in organic synthesis. The synthesis of polysubstituted pyrazoles has attracted much attention and developed rapidly in recent years. Herein, the recent research progress in the construction of polysubstituted pyrazoles is summarized.

参考文献

[1] (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.
[2] (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.
[3] Geng, R.; Zhao, Y.; Li, Y.; Liu, X.; Wang, M. Chin. J. Org. Chem. 2019, 39, 3574(in Chinese). (耿瑞, 赵宇, 李益豪, 刘鑫磊, 王明安, 有机化学, 2019, 39, 3574.)
[4] 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). (钟良坤, 江涛, 张帆, 付庆, 刘幸海, 许天明, 丁成荣, 陈杰, 袁静, 谭成侠, 有机化学, 2019, 39, 2655.)
[5] Gong, C. C.; Tan, H. Y.; Zhang, Q. Chin. J. Org. Chem. 2018, 38, 3086(in Chinese). (龚超超, 谈寒一, 张倩, 有机化学, 2018, 38, 3086.)
[6] He, B.; Wang, D. W.; Yang, W. C.; Chen, Q.; Yang, G. F. Chin. J. Org. Chem. 2017, 37, 2895(in Chinese). (何波, 王大伟, 杨文超, 陈琼, 杨光富, 有机化学, 2017, 37, 2895.)
[7] 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.
[8] 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). (孙娜波, 沈钟华, 翟志文, 韩亮, 翁建全, 谭成侠, 刘幸海, 有机化学, 2017, 37, 2705.)
[9] 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). (石玉军, 周钱, 王杨, 钱宏炜, 叶林玉, 冯霞, 陈辉, 李雅婷, 戴红, 魏中昊, 吴锦明, 有机化学, 2018, 38, 2450.)
[10] 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.
[11] Abd El Razik, H. A.; Badr, M. H.; Atta, A. H.; Mouneir, S. M.; Abu-Serie, M. M. Arch. Pharm. 2017, 350, e1700026.
[12] Schmidt, A.; Dreger, A. Curr. Org. Chem. 2011, 15, 1423.
[13] (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.
[14] 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.
[15] Bhosle, M. R.; Mali, J. R.; Pal, S.; Srivastava, A. K.; Mane, R. A. Bioorg. Med. Chem. Lett. 2014, 24, 2651.
[16] 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.
[17] 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.
[18] 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.
[19] 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.
[20] 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.
[21] Barth, F.; Rinaldi-Carmona, M. Curr. Med. Chem. 1999, 6, 745.
[22] 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.
[23] Labroli, M. A.; Dwyer, M. P.; Poker, C.; Keertikar, K. M.; Rossman, R.; Guzi, T. J. Tetrahedron Lett. 2016, 57, 2601.
[24] Knorr, L. Ber. Dtsch. Chem. Ges. 1883, 16, 2593.
[25] Singh, S. P.; Kumar, D.; Batra, H.; Naithani, R.; Rozas, I.; Elguero, J. Can. J. Chem. 2000, 78, 1109.
[26] Oliveira, D. H.; Aquino, T. B.; Nascimento, J. E. R.; Perin, G.; Jacob, R. G.; Alves, D. Adv. Synth. Catal. 2015, 357, 4041.
[27] Zora, M.; Demirci, D.; Kivrak, A.; Kelgokmen, Y. Tetrahedron Lett. 2016, 57, 993.
[28] Sun, P.; Yang, D.; Wei, W.; Sun, X.; Zhang, W.; Zhang, H.; Wang, Y.; Wang, H. Tetrahedron 2017, 73, 2022.
[29] Kalita, S. J.; Bayan, R.; Devi, J.; Brahma, S.; Mecadon, H.; Deka, D. C. Tetrahedron Lett. 2017, 58, 566.
[30] Zhang, H.; Wei, Q.; Zhu, G.; Qu, J.; Wang, B. Tetrahedron Lett. 2016, 57, 2633.
[31] Markovic, V.; Joksovic, M. D. Green Chem. 2015, 17, 842.
[32] Vekariya, R. H.; Patel, K. D.; Patel, H. D. Res. Chem. Intermed. 2016, 42, 4683.
[33] Saha, A.; Payra, S.; Banerjee, S. Green Chem. 2015, 17, 2859.
[34] Sun, A.; Ye, J. H.; Yu, H.; Zhang, W.; Wang, X. Tetrahedron Lett. 2014, 55, 889.
[35] Kong, Y.; Tang, M.; Wang, Y. Org. Lett. 2014, 16, 576.
[36] Tang, M.; Wang, Y.; Wang, H.; Kong, Y. Synthesis 2016, 48, 3065.
[37] Senadi, G. C.; Hu, W. P.; Lu, T. Y.; Garkhedkar, A. M.; Vandavasi, J. K.; Wang, J. J. Org Lett. 2015, 17, 1521.
[38] Alizadeh, A.; Moafi, L.; Zhu, L. G. Synlett 2016, 27, 595.
[39] Shi, C.; Ma, C.; Ma, H.; Zhou, X.; Cao, J.; Fan, Y.; Huang, G. Tetrahedron 2016, 72, 4055.
[40] Yu, Y.; Huang, W.; Chen, Y.; Gao, B.; Wu, W.; Jiang, H. Green Chem. 2016, 18, 6445.
[41] Mukherjee, S.; Kundu, A.; Pramanik, A. Tetrahedron Lett. 2016, 57, 2103.
[42] Zhang, G.; Ni, H.; Chen, W.; Shao, J.; Liu, H.; Chen, B.; Yu, Y. Org. Lett. 2013, 15, 5967.
[43] Zhang, J.; Chen, W.; Huang, D.; Zeng, X.; Wang, X.; Hu, Y. Tetrahedron Lett. 2017, 58, 4133.
[44] Kumar, R.; Nair, D.; Namboothiri, I. N. N. Tetrahedron 2014, 70, 179.
[45] Nair, D.; Pavashe, P.; Katiyar, S.; Namboothiri, I. N. N. Tetrahedron Lett. 2016, 57, 3146.
[46] Ahamad, S.; Gupta, A. K.; Kant, R.; Mohanan, K. Org. Biomol. Chem. 2015, 13, 1492.
[47] Shao, Y.; Tong, J.; Zhao, Y.; Zheng, H.; Ma, L.; Ma, M.; Wan, X. Org. Biomol. Chem. 2016, 14, 8486.
[48] (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.
[49] Yadav, S.; Rai, P.; Srivastava, M.; Singh, J.; Tiwari, K. P.; Singh, J. Tetrahedron Lett. 2015, 56, 5831.
[50] Cheng, J.; Li, W.; Duan, Y.; Cheng, Y.; Yu, S.; Zhu, C. Org. Lett. 2017, 19, 214.
[51] Dhage, Y. D.; Daimon, H.; Peng, C.; Kusakabe, T.; Takahashi, K.; Kanno, Y.; Inouye, Y.; Kato, K. Org. Biomol. Chem. 2014, 12, 8619.
[52] Li, D. Y.; Mao, X. F.; Chen, H. J.; Chen, G. R.; Liu, P. N. Org. Lett. 2014, 16, 3476.
[53] Tu, Y.; Zhang, Z.; Wang, T.; Ke, J.; Zhao, J. Org. Lett. 2017, 19, 3466.
[54] Zhu, Y.; Lu, W. T.; Sun, H. C.; Zhan, Z. P. Org. Lett. 2013, 15, 4146.
[55] Yang, Y.; Hu, Z. L.; Li, R. H.; Chen, Y. H.; Zhan, Z. P. Org. Biomol. Chem. 2018, 16, 197.
[56] Schmitt, D. C.; Taylor, A. P.; Flick, A. C.; Kyne, R. E. Org. Lett. 2015, 17, 1405.
[57] Chen, B.; Zhu, C.; Tang, Y.; Ma, S. Chem. Commun. 2014, 50, 7677.
[58] Tang, X.; Huang, L.; Yang, J.; Xu, Y.; Wu, W.; Jiang, H. Chem. Commun. 2014, 50, 14793.
[59] Mamaghani, M.; Hossein, R.; Shirini, F.; Tabatabaeian, K.; Rassa, M. Med. Chem. Res. 2015, 24, 1916.
[60] 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.
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