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2019 , Vol. 39 >Issue 11: 3190 - 3198

DOI: https://doi.org/10.6023/cjoc201904070

研究论文

KIO3促进的直接合成硫化或磺酰化吡唑啉酮及其抗菌活性

  • 董道青 ,
  • 陈文静 ,
  • 陈德茂 ,
  • 李丽霞 ,
  • 李光辉 ,
  • 王祖利 ,
  • 邓企 ,
  • 龙姝
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  • a 青岛农业大学化学与药学院 青岛 266109
    b 湖南科技大学化学与化学工程学院 湘潭 411201
    c 长沙理工大学化学与食品工程学院 电力与交通材料保护湖南省重点实验室 长沙 410114

收稿日期: 2019-04-29

  网络出版日期: 2019-07-03

基金资助

国家自然科学基金(21402103);国家自然科学基金(21772107);中国博士后基金(150030);青岛农业大学高层次人才基金(631303)

收起

Direct Synthesis of Sulfonated or Sulfenylated Pyrazolones Mediated by KIO3 and Their Anti-microbial Activity

  • Daoqing Dong ,
  • Wenjing Chen ,
  • Demao Chen ,
  • Lixia Li ,
  • Guanghui Li ,
  • Zuli Wang ,
  • Qi Deng ,
  • Shu Long
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  • a College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109
    b School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201
    c School of Chemistry and Food Engineering, Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Changsha University of Science and Technology, Changsha 410114

Received date: 2019-04-29

  Online published: 2019-07-03

Supported by

the National Natural Science Foundation of China(21402103);the National Natural Science Foundation of China(21772107);the China Postdoctoral Science Foundation(150030);the Research Fund of Qingdao Agricultural University's Highlevel Person(631303)

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摘要

A facile and efficient method for the synthesis of sulfonated or sulfenylated pyrazolones catalyzed by KIO3 was established. A variety of desired products were obtained in moderate to high yields. This methodology could be conducted under mild reaction conditions without requiring any metal. Control experiments showed that the mechanism of this reaction was different from previous KIO3-catalyzed reactions. Some of these desired products showed high inhibitory activity against V. mali and B. cinerea.

关键词： C-S键; 磺酰化; 硫化; 吡唑啉酮; 碘试剂; 抑菌活性; C-S bond; sulfonylation; sulfenylation; pyrazolones; iodine reagents; anti-microbial activity

本文引用格式

董道青 , 陈文静 , 陈德茂 , 李丽霞 , 李光辉 , 王祖利 , 邓企 , 龙姝 . KIO3促进的直接合成硫化或磺酰化吡唑啉酮及其抗菌活性[J]. 有机化学, 2019 , 39(11) : 3190 -3198 . DOI: 10.6023/cjoc201904070

参考文献

[1] (a) Elguero, J. Comprehensive Heterocyclic Chemistry, Eds.: Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Pergamon, Oxford, UK, 1996, p. 167.
[1] (b) Liu, X. H.; Cui, P.; Song, B. A.; Bhadury, P. S.; Zhu, H. L.; Wang, S. F. Bioorg. Med. Chem. 2008, 16, 4075.
[1] (c) Velaparthi, S.; Brunsteiner, M.; Uddin, R.; Wan, B.; Franzblau, S. G.; Petukhov, P. A. J. Med. Chem. 2008, 51, 1999.
[1] (d) Magedov, I. V.; Manpadi, M.; Slambrouck, V. S.; Steelant, W. F. A.; Rozhkova, E.; Przheval'skii, N. M.; Rogelj, S.; Kornienko, A. J. Med. Chem. 2007, 50, 5183.
[1] (e) Vicentini, C. B.; Romagnoli, C.; Reotti, E.; Mares, D. J. Agric. Food Chem. 2007, 55, 10331.
[1] (f) Vicentini, C. B.; Guccione, S.; Giurato, L.; Ciaccio, R.; Mares, D.; Forlani, G. J. Agric. Food Chem. 2005, 53, 3848.
[1] (g) Peng, L.; Hu, Z.; Tang, Z.; Jiao, Y.; Xu, X. Chin. Chem. Lett. 2019, 30, 1481.
[1] (h) Liang, Q.; Zhang, Y.; Zeng, M.; Guan, L.; Xiao, Y.; Xiao, F. Toxicol. Res. 2018, 7, 521.
[1] (i) Jiang, H.; Tang, X.; Xu, Z.; Wang, H.; Han, K.; Yang, X.; Zhou, Y.; Feng, Y.; Yu, X.; Gui, Q. Org. Biomol. Chem. 2019, 17, 2715.
[1] (j) Li, G.; Gan, Z.; Kong, K.; Dou, X.; Yang, D. Adv. Synth. Catal. 2019, 361, 1808.
[2] Kawakubo K. Shindo M. Konotsune T. Plant Physiol. 1979 64 774.
[3] Watanabe K. Morinaka Y. Iseki K. Watanabe T. Yuki S. Nishi H. Redox Rep. 2003 8 151.
[4] (a) Wolf, W. M. J. Mol. Struct. 1999, 474, 113.
[4] (b) Petrov, K. G.; Zhang, Y.; Carter, M.; Cockerill, G. S.; Dickerson, S.; Gauthier, C. A.; Guo, Y.; Mook, R. A.; Rusnak, D. W.; Walker, A. L.; Wood, E. R.; Lackey, K. E. Bioorg. Med. Chem. Lett. 2006, 16, 4686.
[4] (c) Ettari, R.; Nizi, E.; Francesco, M. E. D.; Dude, M. A.; Pradel, G.; Vicik, R.; Schirmeister, T.; Micale, N.; Grasso, S.; Zappala, M. J. Med. Chem. 2008, 51, 988.
[5] (a) Kumar, R.; Namboothiri, I. N. N. Org. Lett. 2011, 13, 4016.
[5] (b) Kumar, R.; Verma, D.; Mobin, S. M.; Namboothiri, I. N. N. Org. Lett. 2012, 14, 4070.
[5] (c) Zhu, Y.; Lu, W. T.; Sun, H. C.; Zhan, Z. P. Org. Lett. 2013, 15, 4146.
[5] (d) Jeon, D. J.; Lee, J. N.; Lee, K. C.; Kim, H. R.; Zong, K.; Ryu, E. K. Bull. Korean Chem. Soc. 1998, 19, 1153.
[5] (e) Xu, X. H.; Wang, X.; Liu, G. K.; Tokunaga, E.; Shibata, N. Org. Lett. 2012, 14, 2544.
[6] Wei W. Cui H. Yang D. Liu X. He C. Dai S. Wang H. Org. Chem. Front. 2017 4 26.
[7] (a) Shermolovich, Y. G.; Emets, S. V. Chem. Heterocycl. Compd. 2000, 36, 152.
[7] (b) Li, L.; Hao, S.; Dong, D.; Wang, Z. Tetrahedron. Lett. 2018, 59, 1517.
[8] Zhao X. Zhang L. Li T. Liu G. Wang H. Lu K. Chem. Commun. 2014 50 13121.
[9] Wang D. Guo S. Zhang R. Lin S. Yan Z. RSC Adv. 2016 6 54377.
[10] Liu X. Cui H. Yang D. Dai S. Zhang T. Sun J. Wei W. Wang H. RSC Adv. 2016 6 51830.
[11] Yang D. Sun P. Wei W. Meng L. He L. Fang B. Jiang W. Wang H. Org. Chem. Front. 2016 3 1457.
[12] Hu F. Gao W. Chang H. Li X. Wei W. Chin. J. Org. Chem. 2015 35 1848.
[13] (a) Mphahlele, M. J. Molecules 2009, 14, 4814.
[13] (b) Hummel, S.; Kirsch, S. F. Beilstein J. Org. Chem. 2011, 7, 847.
[14] (a) Zhao, J.; Gao, W.; Chang, H.; Li, X.; Liu, Q.; Wei, W. Chin. J. Org. Chem. 2014, 34, 1941.
[14] (b) Wu, C.; Lu, L. H.; Peng, A. Z.; Jia, G. K.; Peng, C.; Cao, Z.; Tang, Z.; He, W. M.; Xu, X. Green Chem. 2018, 20, 3683.
[14] (c) Bao, W. H.; He, M.; Wang, J.; Peng, T. X.; Sung, M.; Tang, Z.; Jiang, S.; Cao, Z.; He, W. M. J. Org. Chem. 2019, 84, 6065.
[14] (d) Lu, L.-H.; Wang, Z.; Xia, W.; Cheng, P.; Zhang, B.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2019, 30, 1237.
[15] (a) Liu, K.; Song, C.; Lei, A. Org. Biomol. Chem. 2018, 16, 2375.
[15] (b) Nguyen, T. B. Asian J. Org. Chem. 2017, 6, 477.
[15] (c) Lauriers, A. J.; Legault. C. Y. Asian J. Org. Chem. 2016, 5, 1078.
[15] (d) Yoshimura, A.; Yusubov, M. S.; Zhdankin. V. V. Org. Biomol. Chem. 2016, 21, 4771.
[15] (e) Aggarwal, T.; Kumar, S.; Verma, A. K. Org. Biomol. Chem. 2016, 14, 7639.
[15] (f) Zhao, J.; Gao, W.; Chang, H.; Li, X.; Liu, Q.; Wei, W. Chin. J. Org. Chem. 2014, 34, 1941.
[15] (g) Finkbeiner, P.; Nachtsheim. B. J. Synthesis 2013, 45, 979.
[15] (h) Liu M.; Huang H.; Chen Y. Chin. J. Chem. 2018, 36, 1209.
[15] (i) Wan, J.; Zhong, S.; Guo, Y.; Wei, L. Eur. J. Org. Chem. 2017, 4401.
[15] (j) Hou J.; Zhang X.; Yu W.; Chang J. Chin. J. Org. Chem. 2018, 38, 3236.
[15] (k) Lu, L. H.; Zhou, S. J.; He, W. B.; Xia, W.; Chen, P.; Yu, X.; Xu, X.; He, W. M. Org. Biomol. Chem. 2018, 16, 9064.
[15] (l) Bao, W. H.; Wu, C.; Wang, J. T.; Xia, W.; Chen, P.; Tang, Z.; Xu, X., He, W. M. Org. Biomol. Chem. 2018, 16, 8403.
[15] (m) Lu, L. H.; Zhou, S. J.; Sun, M.; Chen, J. L.; Xia, W.; Yu, X.; Xu, X.; He, W. M. ACS Sustainable Chem. Eng. 2019, 7, 1574.
[15] (n) Tang, Y. Ran, S.; Wang, P.; Chen, P. Chin. J. Org. Chem. 2019, 39, 1116 (in Chinese).
[15] (唐裕才, 冉书童, 王萍, 陈飘, 有机化学, 2019, 39, 1116.)
[15] (o) Zhu, F.; Wang, Y.; He, M.; Yan, Z.; Lin, S. Chin. J. Org. Chem. 2019, 39, 1175 (in Chinese).
[15] (朱福元, 王彦梅, 何明闯, 严兆华, 林森, 有机化学, 2019, 39, 1175.)
[16] (a) Hao, S.; Li, L.; Dong, D.; Wang, Z. Chin. J. Catal. 2017, 38, 1664.
[16] (b) Dong, D.; Hao, S.; Yang, D.; Li, L.; Wang, Z. Eur. J. Org. Chem. 2017, 6576.
[16] (c) Dong, D.; Zhang, H.; Wang, Z. RSC Adv. 2017, 7, 3780.
[16] (d) Zhang, H.; Dong, D.; Hao, S.; Wang, Z. RSC Adv. 2016, 6, 8465.
[16] (e) Dong, D. Q.; Chen, W. J.; Yang, Y.; Gao, X.; Wang, Z. L. ChemistrySelect 2019, 4, 2480.
[16] (f) Hao, S.; Li, L.; Dong, D.; Wang, Z.; Yu, X. Tetrahedron Lett. 2018, 59, 4073.
[16] (g) Li, G. H.; Dong, D. Q.; Yu, X. Y.; Wang, Z. L. New J. Chem. 2019, 43, 1667.
[16] (h) Li, G. H.; Dong, D. Q.; Yang, Y.; Yu, X. Y.; Wang, Z. L. Adv. Synth. Catal. 2019, 361, 832.
[16] (i) Yan, S.; Dong, D.-Q.; Xie, C.; Wang, W.; Wang, Z.-L. Chin. J. Org. Chem. 2019, 39, 2560 (in Chinese).
[16] (颜世强, 董道青, 解春文, 王文笙, 王祖利, 有机化学, 2019, 39, 2560.)
[16] (j) Li, G. H.; Dong, D. Q.; Deng, Q.; Yan, S. Q.; Wang, Z. L. Synthesis 2019, 51, 3313..
[16] (k) Xie, L. Y.; Peng, S.; Liu, F.; Chen, G. R.; Xia, W.; Yu, X.; Li, W. F.; Cao, Z.; He, W. M. Org. Chem. Front. 2018, 5, 2604.
[16] (l) Xie, L. Y.; Peng, S.; Jiang, L. L.; Peng, X.; Xia, W.; Yu, X.; Wang, X. X.; Cao, Z.; He, W. M. Org. Chem. Front. 2019, 2, 167.
[16] (m) Xu, X. M.; Chen, D. M.; Wang, Z. L. Chin. Chem. Lett. 2019,
[16] (n)Dong, D.Q.; Hao, S.Zhang, H.; Wang,Z.L.Chin.Chem.Lett.2017,28, 1597.
[17] Qiao L. Wei Y. Hao S. Chin. J. Org. Chem. 2018 38 509.
[17] 乔 丽丽 魏 艳 郝 双红 有机化学 2018 38 509.
[18] Jin H. Geng Y. Yu Z. Tao K. Hou T. Pestic. Biochem. Physiol. 2009 93 133.
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