KIO3促进的直接合成硫化或磺酰化吡唑啉酮及其抗菌活性

doi:10.6023/cjoc201904070

有机化学 ›› 2019, Vol. 39 ›› Issue (11): 3190-3198.DOI: 10.6023/cjoc201904070 上一篇下一篇

所属专题：元素有机化学合辑2018-2019

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^a, 陈文静^a, 陈德茂^a, 李丽霞^a, 李光辉^a, 王祖利^a*(), 邓企^b, 龙姝^c

^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 发布日期:2019-07-03
通讯作者: 王祖利 E-mail:wangzulichem@163.com
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)

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

Dong Daoqing^a, Chen Wenjing^a, Chen Demao^a, Li Lixia^a, Li Guanghui^a, Wang Zuli^a*(), Deng Qi^b, Long Shu^c

^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:2019-04-29 Published:2019-07-03
Contact: Wang Zuli E-mail:wangzulichem@163.com
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/Abstract

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

引用此文

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.

Dong Daoqing, Chen Wenjing, Chen Demao, Li Lixia, Li Guanghui, Wang Zuli, Deng Qi, Long Shu. Direct Synthesis of Sulfonated or Sulfenylated Pyrazolones Mediated by KIO₃ and Their Anti-microbial Activity[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3190-3198.

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[1]	(a) Elguero, J. Comprehensive Heterocyclic Chemistry, Eds.: Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Pergamon, Oxford, UK, 1996, p. 167. doi: 10.1021/jm701372r
	(b) Liu, X. H.; Cui, P.; Song, B. A.; Bhadury, P. S.; Zhu, H. L.; Wang, S. F. Bioorg. Med. Chem. 2008, 16, 4075. doi: 10.1021/jm701372r
	(c) Velaparthi, S.; Brunsteiner, M.; Uddin, R.; Wan, B.; Franzblau, S. G.; Petukhov, P. A. J. Med. Chem. 2008, 51, 1999. doi: 10.1021/jm701372r
	(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. doi: 10.1021/jm701372r
	(e) Vicentini, C. B.; Romagnoli, C.; Reotti, E.; Mares, D. J. Agric. Food Chem. 2007, 55, 10331. doi: 10.1021/jm701372r
	(f) Vicentini, C. B.; Guccione, S.; Giurato, L.; Ciaccio, R.; Mares, D.; Forlani, G. J. Agric. Food Chem. 2005, 53, 3848. doi: 10.1021/jm701372r
	(g) Peng, L.; Hu, Z.; Tang, Z.; Jiao, Y.; Xu, X. Chin. Chem. Lett. 2019, 30, 1481. doi: 10.1021/jm701372r
	(h) Liang, Q.; Zhang, Y.; Zeng, M.; Guan, L.; Xiao, Y.; Xiao, F. Toxicol. Res. 2018, 7, 521. doi: 10.1021/jm701372r
	(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. doi: 10.1021/jm701372r
	(j) Li, G.; Gan, Z.; Kong, K.; Dou, X.; Yang, D. Adv. Synth. Catal. 2019, 361, 1808. doi: 10.1021/jm701372r
[2]	Kawakubo K. Shindo M. Konotsune T. Plant Physiol. 1979 64 774. doi: 10.1104/pp.64.5.774
[3]	Watanabe K. Morinaka Y. Iseki K. Watanabe T. Yuki S. Nishi H. Redox Rep. 2003 8 151. doi: 10.1179/135100003225001520
[4]	(a) Wolf, W. M. J. Mol. Struct. 1999, 474, 113. doi: 10.1016/S0022-2860(98)00565-1
	(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. doi: 10.1016/S0022-2860(98)00565-1
	(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. doi: 10.1016/S0022-2860(98)00565-1
[5]	(a) Kumar, R.; Namboothiri, I. N. N. Org. Lett. 2011, 13, 4016. doi: 10.1021/ol201534f
	(b) Kumar, R.; Verma, D.; Mobin, S. M.; Namboothiri, I. N. N. Org. Lett. 2012, 14, 4070. doi: 10.1021/ol201534f
	(c) Zhu, Y.; Lu, W. T.; Sun, H. C.; Zhan, Z. P. Org. Lett. 2013, 15, 4146. doi: 10.1021/ol201534f
	(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. doi: 10.1021/ol201534f
	(e) Xu, X. H.; Wang, X.; Liu, G. K.; Tokunaga, E.; Shibata, N. Org. Lett. 2012, 14, 2544. doi: 10.1021/ol201534f
[6]	Wei W. Cui H. Yang D. Liu X. He C. Dai S. Wang H. Org. Chem. Front. 2017 4 26. doi: 10.1039/C6QO00403B
[7]	(a) Shermolovich, Y. G.; Emets, S. V. Chem. Heterocycl. Compd. 2000, 36, 152. doi: 10.1007/BF02283543
	(b) Li, L.; Hao, S.; Dong, D.; Wang, Z. Tetrahedron. Lett. 2018, 59, 1517. doi: 10.1007/BF02283543
[8]	Zhao X. Zhang L. Li T. Liu G. Wang H. Lu K. Chem. Commun. 2014 50 13121. doi: 10.1039/C4CC05237D
[9]	Wang D. Guo S. Zhang R. Lin S. Yan Z. RSC Adv. 2016 6 54377. doi: 10.1039/C6RA02302A
[10]	Liu X. Cui H. Yang D. Dai S. Zhang T. Sun J. Wei W. Wang H. RSC Adv. 2016 6 51830. doi: 10.1039/C6RA09739A
[11]	Yang D. Sun P. Wei W. Meng L. He L. Fang B. Jiang W. Wang H. Org. Chem. Front. 2016 3 1457. doi: 10.1039/C6QO00407E
[12]	Hu F. Gao W. Chang H. Li X. Wei W. Chin. J. Org. Chem. 2015 35 1848. doi: 10.6023/cjoc201504039
[13]	(a) Mphahlele, M. J. Molecules 2009, 14, 4814. doi: 10.3390/molecules14124814
	(b) Hummel, S.; Kirsch, S. F. Beilstein J. Org. Chem. 2011, 7, 847. doi: 10.3390/molecules14124814
[14]	(a) Zhao, J.; Gao, W.; Chang, H.; Li, X.; Liu, Q.; Wei, W. Chin. J. Org. Chem. 2014, 34, 1941. doi: 10.6023/cjoc201405003
	(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. doi: 10.6023/cjoc201405003
	(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. doi: 10.6023/cjoc201405003
	(d) Lu, L.-H.; Wang, Z.; Xia, W.; Cheng, P.; Zhang, B.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2019, 30, 1237. doi: 10.6023/cjoc201405003
[15]	(a) Liu, K.; Song, C.; Lei, A. Org. Biomol. Chem. 2018, 16, 2375. doi: 10.6023/cjoc201810002
	(b) Nguyen, T. B. Asian J. Org. Chem. 2017, 6, 477. doi: 10.6023/cjoc201810002
	(c) Lauriers, A. J.; Legault. C. Y. Asian J. Org. Chem. 2016, 5, 1078. doi: 10.6023/cjoc201810002
	(d) Yoshimura, A.; Yusubov, M. S.; Zhdankin. V. V. Org. Biomol. Chem. 2016, 21, 4771. doi: 10.6023/cjoc201810002
	(e) Aggarwal, T.; Kumar, S.; Verma, A. K. Org. Biomol. Chem. 2016, 14, 7639. doi: 10.6023/cjoc201810002
	(f) Zhao, J.; Gao, W.; Chang, H.; Li, X.; Liu, Q.; Wei, W. Chin. J. Org. Chem. 2014, 34, 1941. doi: 10.6023/cjoc201810002
	(g) Finkbeiner, P.; Nachtsheim. B. J. Synthesis 2013, 45, 979. doi: 10.6023/cjoc201810002
	(h) Liu M.; Huang H.; Chen Y. Chin. J. Chem. 2018, 36, 1209. doi: 10.6023/cjoc201810002
	(i) Wan, J.; Zhong, S.; Guo, Y.; Wei, L. Eur. J. Org. Chem. 2017, 4401. doi: 10.6023/cjoc201810002
	(j) Hou J.; Zhang X.; Yu W.; Chang J. Chin. J. Org. Chem. 2018, 38, 3236. doi: 10.6023/cjoc201810002
	(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. doi: 10.6023/cjoc201810002
	(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. doi: 10.6023/cjoc201810002
	(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. doi: 10.6023/cjoc201810002
	(n) Tang, Y. Ran, S.; Wang, P.; Chen, P. Chin. J. Org. Chem. 2019, 39, 1116 (in Chinese). doi: 10.6023/cjoc201810002
	(唐裕才, 冉书童, 王萍, 陈飘, 有机化学, 2019, 39, 1116.) doi: 10.6023/cjoc201810002
	(o) Zhu, F.; Wang, Y.; He, M.; Yan, Z.; Lin, S. Chin. J. Org. Chem. 2019, 39, 1175 (in Chinese). doi: 10.6023/cjoc201810002
	(朱福元, 王彦梅, 何明闯, 严兆华, 林森, 有机化学, 2019, 39, 1175.) doi: 10.6023/cjoc201810002
[16]	(a) Hao, S.; Li, L.; Dong, D.; Wang, Z. Chin. J. Catal. 2017, 38, 1664. doi: 10.6023/cjoc201901023
	(b) Dong, D.; Hao, S.; Yang, D.; Li, L.; Wang, Z. Eur. J. Org. Chem. 2017, 6576. doi: 10.6023/cjoc201901023
	(c) Dong, D.; Zhang, H.; Wang, Z. RSC Adv. 2017, 7, 3780. doi: 10.6023/cjoc201901023
	(d) Zhang, H.; Dong, D.; Hao, S.; Wang, Z. RSC Adv. 2016, 6, 8465. doi: 10.6023/cjoc201901023
	(e) Dong, D. Q.; Chen, W. J.; Yang, Y.; Gao, X.; Wang, Z. L. ChemistrySelect 2019, 4, 2480. doi: 10.6023/cjoc201901023
	(f) Hao, S.; Li, L.; Dong, D.; Wang, Z.; Yu, X. Tetrahedron Lett. 2018, 59, 4073. doi: 10.6023/cjoc201901023
	(g) Li, G. H.; Dong, D. Q.; Yu, X. Y.; Wang, Z. L. New J. Chem. 2019, 43, 1667. doi: 10.6023/cjoc201901023
	(h) Li, G. H.; Dong, D. Q.; Yang, Y.; Yu, X. Y.; Wang, Z. L. Adv. Synth. Catal. 2019, 361, 832. doi: 10.6023/cjoc201901023
	(i) Yan, S.; Dong, D.-Q.; Xie, C.; Wang, W.; Wang, Z.-L. Chin. J. Org. Chem. 2019, 39, 2560 (in Chinese). doi: 10.6023/cjoc201901023
	(颜世强, 董道青, 解春文, 王文笙, 王祖利, 有机化学, 2019, 39, 2560.) doi: 10.6023/cjoc201901023
	(j) Li, G. H.; Dong, D. Q.; Deng, Q.; Yan, S. Q.; Wang, Z. L. Synthesis 2019, 51, 3313.. doi: 10.6023/cjoc201901023
	(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. doi: 10.6023/cjoc201901023
	(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. doi: 10.6023/cjoc201901023
	(m) Xu, X. M.; Chen, D. M.; Wang, Z. L. Chin. Chem. Lett. 2019, doi: 10.6023/cjoc201901023
	(n)Dong, D.Q.; Hao, S.Zhang, H.; Wang,Z.L.Chin.Chem.Lett.2017,28, 1597. doi: 10.6023/cjoc201901023
[17]	Qiao L. Wei Y. Hao S. Chin. J. Org. Chem. 2018 38 509. doi: 10.6023/cjoc201708004
	乔丽丽魏艳郝双红有机化学 2018 38 509. doi: 10.6023/cjoc201708004
[18]	Jin H. Geng Y. Yu Z. Tao K. Hou T. Pestic. Biochem. Physiol. 2009 93 133. doi: 10.1016/j.pestbp.2009.01.002


Entry	Catalyst (equiv.)	Solvent	T/℃	Yield/%
1	KIO₃ (0.30)	DMSO	100	35
2	KIO₃ (0.30)	1, 2-Dimethoxyethane	100	40
3	KIO₃ (0.30)	EtOH	100	62
4	KIO₃ (0.30)	THF	100	24
5	KIO₃ (0.30)	Ethylene glycol	100	48
6	KIO₃ (0.30)	CH₃CN	100	Trace
7	KIO₃ (0.30)	CHCl₃	100	Trace
8	KIO₃ (0.30)	1, 2-Dichloroethane	100	Trace
9	KIO₃ (0.30)	1, 4-Dioxane	100	Trace
10	KIO₃ (0.30)	Toluene	100	Trace
11	KIO₃ (0.30)	EtOH	120	86
12	KIO₃ (0.30)	EtOH	130	86
13	KIO₃ (0.20)	EtOH	120	78
14^b	—	EtOH	120	NR
15	KCl	EtOH	120	NR
16^c	KIO₃ (0.30)	EtOH	120	83


Entry	Catalyst (equiv.)	Solvent	T/℃	Yield/%
1	KIO₃ (0.30)	DMSO	100	35
2	KIO₃ (0.30)	1, 2-Dimethoxyethane	100	40
3	KIO₃ (0.30)	EtOH	100	62
4	KIO₃ (0.30)	THF	100	24
5	KIO₃ (0.30)	Ethylene glycol	100	48
6	KIO₃ (0.30)	CH₃CN	100	Trace
7	KIO₃ (0.30)	CHCl₃	100	Trace
8	KIO₃ (0.30)	1, 2-Dichloroethane	100	Trace
9	KIO₃ (0.30)	1, 4-Dioxane	100	Trace
10	KIO₃ (0.30)	Toluene	100	Trace
11	KIO₃ (0.30)	EtOH	120	86
12	KIO₃ (0.30)	EtOH	130	86
13	KIO₃ (0.20)	EtOH	120	78
14^b	—	EtOH	120	NR
15	KCl	EtOH	120	NR
16^c	KIO₃ (0.30)	EtOH	120	83

Compd.	V. mali	B. cinerea	C. glecosporioides
C4	82.63	78.15	25.81
E2	81.38	58.82	24.26
E12	81.12	66.39	50.52
E14	83.33	56.17	39.69
E16	81.67	34.40	38.92
E15	70.34	38.25	26.29
E11	75.34	52.9	20.73
E3	57.66	56.15	11.11

Compd.	V. mali	B. cinerea	C. glecosporioides
C4	82.63	78.15	25.81
E2	81.38	58.82	24.26
E12	81.12	66.39	50.52
E14	83.33	56.17	39.69
E16	81.67	34.40	38.92
E15	70.34	38.25	26.29
E11	75.34	52.9	20.73
E3	57.66	56.15	11.11

KIO₃促进的直接合成硫化或磺酰化吡唑啉酮及其抗菌活性

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

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