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

doi:10.6023/cjoc201904070

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3190-3198.DOI: 10.6023/cjoc201904070 Previous Articles Next Articles

Special Issue: 元素有机化学合辑2018-2019

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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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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References 18

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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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References 18

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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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PDF

Supporting Info.

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Abstract

Cite this article

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Fig. & Tab. 6

References 18

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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