Direct Sulfonylation of Pyrazolones with Sulfonyl Chlorides to Synthesize Pyrazolyl Sulfonates

doi:10.6023/cjoc202312008

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 1998-2005.DOI: 10.6023/cjoc202312008 Previous Articles Next Articles

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吡唑啉酮与磺酰氯的直接磺酰化合成吡唑磺酸酯

王斌^a^,^b^,^*(), 韩万仓^b, 代林林^b, 张永红^b, 夏昱^b, 金伟伟^b, 刘晨江^b^,^c^,^*()

a 新疆大学分析测试中心乌鲁木齐 830017
b 新疆大学化学学院碳基能源化学与利用国家重点实验室石油天然气精细化工教育部暨新疆维吾尔自治区重点实验室乌鲁木齐绿色催化与合成技术重点实验室乌鲁木齐 830017
c 新疆大学未来技术学院乌鲁木齐 830017

收稿日期:2023-12-08 修回日期:2024-01-21 发布日期:2024-02-19
基金资助:
国家自然科学基金(21762041); 国家自然科学基金(21861036); 国家自然科学基金(21961037); 新疆维吾尔自治区自然科学基金(2022E01042); 新疆维吾尔自治区自然科学基金(2022TSYCCX0024); 新疆维吾尔自治区自然科学基金(2021D01E10)

Direct Sulfonylation of Pyrazolones with Sulfonyl Chlorides to Synthesize Pyrazolyl Sulfonates

Bin Wang^a^,^b,*(), Wancang Han^b, Linlin Dai^b, Yonghong Zhang^b, Yu Xia^b, Weiwei Jin^b, Chenjiang Liu^b^,^c,*()

a Analysis and Testing Center, Xinjiang University, Urumqi 830017
b Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Oil and Gas Fine Chemicals of Ministry of Education & Xinjiang Uygur Autonomous Region, State Key Laboratory of Chemistry and Utilization of Carbon-Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017
c College of Future Technology, Xinjiang University, Urumqi 830017

Received:2023-12-08 Revised:2024-01-21 Published:2024-02-19
Contact: * E-mail: wangbin_284992269@126.com; pxylcj@126.com
Supported by:
National Natural Science Foundation of China(21762041); National Natural Science Foundation of China(21861036); National Natural Science Foundation of China(21961037); Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2022E01042); Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2022TSYCCX0024); Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2021D01E10)

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Abstract

Pyrazole as a core framework exists in many bioactive molecules and has a wide range of applications in pharmaceuticals, agricultural chemicals and other functional materials. Sulfonates are important intermediates in organic synthesis and play a very important role in organic chemistry. A green and efficient method for the synthesis of pyrazolyl sulfonate compounds by using pyrazolones and sulfonyl chlorides as starting materials was developed. This method features the advantages of simple and easy to operate, without the need for any additives, metal or oxidant. It only requires room temperature and water as the solvent to efficiently synthesize important pyrazolyl sulfonates. The smooth progress of the gram scale reaction and product transformation further proves the practicality of this method.

Key words: pyrazolone, sulfonyl chloride, sulfonylation, pyrazolyl sulfonate

Cite this article

Bin Wang, Wancang Han, Linlin Dai, Yonghong Zhang, Yu Xia, Weiwei Jin, Chenjiang Liu. Direct Sulfonylation of Pyrazolones with Sulfonyl Chlorides to Synthesize Pyrazolyl Sulfonates[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1998-2005.

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References 21

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Entry	1a	2a	Solvent	Time/h	Yield^b/%
1	0.2	0.4	CH₃CN	20	70 (74)^c
2	0.2	0.4	C₂H₅OH	20	34
3	0.2	0.4	EA	20	62
4	0.2	0.4	DCM	20	77
5	0.2	0.4	THF	20	69
6	0.2	0.4	DMF	20	10
7	0.2	0.4	DMSO	20	0
8	0.2	0.4	H₂O	20	89
9	0.2	0.2	H₂O	20	38
10	0.2	0.24	H₂O	20	58
11	0.2	0.3	H₂O	20	78
12	0.2	0.4	H₂O	16	96
13	0.2	0.4	H₂O	12	97
14	0.2	0.4	H₂O	8	84

Entry	1a	2a	Solvent	Time/h	Yield^b/%
1	0.2	0.4	CH₃CN	20	70 (74)^c
2	0.2	0.4	C₂H₅OH	20	34
3	0.2	0.4	EA	20	62
4	0.2	0.4	DCM	20	77
5	0.2	0.4	THF	20	69
6	0.2	0.4	DMF	20	10
7	0.2	0.4	DMSO	20	0
8	0.2	0.4	H₂O	20	89
9	0.2	0.2	H₂O	20	38
10	0.2	0.24	H₂O	20	58
11	0.2	0.3	H₂O	20	78
12	0.2	0.4	H₂O	16	96
13	0.2	0.4	H₂O	12	97
14	0.2	0.4	H₂O	8	84

吡唑啉酮与磺酰氯的直接磺酰化合成吡唑磺酸酯

Direct Sulfonylation of Pyrazolones with Sulfonyl Chlorides to Synthesize Pyrazolyl Sulfonates

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