One-Pot Synthesis ofN-Furanonyl Sulfonyl Hydrazone Compounds

doi:10.6023/cjoc202102015

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2750-2759.DOI: 10.6023/cjoc202102015 Previous Articles Next Articles

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一锅法合成N-呋喃酮基磺酰腙类化合物

陈任宏^a^,^*(), 吴桂贞^a, 杨凯^c^,^*(), 叶斌^a, 陈庆凤^a, 汪朝阳^b^,^*()

a 广东食品药品职业学院广州 510520
b 华南师范大学化学学院教育部环境理论化学重点实验室广州 510006
c 赣南医学院药学院江西赣州 341000

收稿日期:2021-02-02 修回日期:2021-03-22 发布日期:2021-04-16
通讯作者: 陈任宏, 杨凯, 汪朝阳
基金资助:
广东食品药品职业学院自然科学研究(2018ZR001); 广东食品药品职业学院自然科学研究(2014YZ007); 江西省教育厅科学研究(GJJ201504); 赣南医学院科学研究(YB201903); 广东省基础与应用基础研究基金(2021A1515012342); 广东省科技计划(2017A010103016)

One-Pot Synthesis ofN-Furanonyl Sulfonyl Hydrazone Compounds

Renhong Chen^a(), Guizhen Wu^a, Kai Yang^c(), Bin Ye^a, Qingfeng Chen^a, Zhaoyang Wang^b()

a Guangdong Food and Drug Vocational College, Guangzhou 510520
b Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry, South China Normal University, Guangzhou 510006
c College of Pharmacy, Gannan Medical University, Ganzhou, Jiangxi 341000

Received:2021-02-02 Revised:2021-03-22 Published:2021-04-16
Contact: Renhong Chen, Kai Yang, Zhaoyang Wang
Supported by:
Natural Science Project of Guangdong Food and Drug Vocational College(2018ZR001); Natural Science Project of Guangdong Food and Drug Vocational College(2014YZ007); Scientific Research Fund of Jiangxi Provincial Education Department(GJJ201504); Scientific Research Project of Gannan Medical University(YB201903); Guangdong Basic and Applied Basic Research Foundation(2021A1515012342); Guangdong Provincial Science and Technology Project(2017A010103016)

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Abstract

An efficient approach for the construction of one C—N bond and one C=N bond based on sulfonyl hydrazides, 3,4-dihalo-2(5H)-furanones and carbonyl compounds via the one-pot strategy to provideN-2(5H)-furanonyl sulfonyl hydrazone products with good yields is described. This approach with wide substrate range and good selectivity can be achieved at room temperature by metal-free catalysts. Even for 3,4-dichloro-2(5H)-furanones, the inactive C_sp2—Cl type compounds, this green method also gives satisfactory yields. Importantly, its application for a gram-scale preparation of different furanone substrates can be accomplished.

Key words: 2(5H)-furanone, sulfonyl hydrazone, synthesis, one-pot reaction, metal-free catalysis

Cite this article

Renhong Chen, Guizhen Wu, Kai Yang, Bin Ye, Qingfeng Chen, Zhaoyang Wang. One-Pot Synthesis ofN-Furanonyl Sulfonyl Hydrazone Compounds[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2750-2759.

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Entry	Additives (the first step)	Acid (the second step)	Yield^b/%
1	2.0 equiv. K₂CO₃	6.0 equiv. HCl	Trace
2	2.0 equiv. K₂CO₃, 0.1 equiv. DMAP	6.0 equiv. HCl	52
3	2.0 equiv. K₂CO₃, 0.2 equiv. DMAP	6.0 equiv. HCl	65
4	2.0 equiv. K₂CO₃, 0.3 equiv. DMAP	6.0 equiv. HCl	79
5	2.0 equiv. K₂CO₃, 0.4 equiv. DMAP	6.0 equiv. HCl	86
6	2.0 equiv. K₂CO₃, 0.5 equiv. DMAP	6.0 equiv. HCl	85
7	2.0 equiv. Cs₂CO₃, 0.4 equiv. DMAP	6.0 equiv. HCl	72
8	2.0 equiv. Na₂CO₃, 0.4 equiv. DMAP	6.0 equiv. HCl	83
9	1.5 equiv. K₂CO₃, 0.4 equiv. DMAP	6.0 equiv. HCl	87
10	1.0 equiv. K₂CO₃, 0.4 equiv. DMAP	6.0 equiv. HCl	70
11	1.5 equiv. K₂CO₃, 0.4 equiv. DMAP	8.0 equiv. HCl	89
12	1.5 equiv. K₂CO₃, 0.4 equiv. DMAP	10.0 equiv. HCl	87
13^c	1.5 equiv. K₂CO₃, 0.4 equiv. DMAP	8.0 equiv. HCl	53

Entry	Additives (the first step)	Acid (the second step)	Yield^b/%
1	2.0 equiv. K₂CO₃	6.0 equiv. HCl	Trace
2	2.0 equiv. K₂CO₃, 0.1 equiv. DMAP	6.0 equiv. HCl	52
3	2.0 equiv. K₂CO₃, 0.2 equiv. DMAP	6.0 equiv. HCl	65
4	2.0 equiv. K₂CO₃, 0.3 equiv. DMAP	6.0 equiv. HCl	79
5	2.0 equiv. K₂CO₃, 0.4 equiv. DMAP	6.0 equiv. HCl	86
6	2.0 equiv. K₂CO₃, 0.5 equiv. DMAP	6.0 equiv. HCl	85
7	2.0 equiv. Cs₂CO₃, 0.4 equiv. DMAP	6.0 equiv. HCl	72
8	2.0 equiv. Na₂CO₃, 0.4 equiv. DMAP	6.0 equiv. HCl	83
9	1.5 equiv. K₂CO₃, 0.4 equiv. DMAP	6.0 equiv. HCl	87
10	1.0 equiv. K₂CO₃, 0.4 equiv. DMAP	6.0 equiv. HCl	70
11	1.5 equiv. K₂CO₃, 0.4 equiv. DMAP	8.0 equiv. HCl	89
12	1.5 equiv. K₂CO₃, 0.4 equiv. DMAP	10.0 equiv. HCl	87
13^c	1.5 equiv. K₂CO₃, 0.4 equiv. DMAP	8.0 equiv. HCl	53

一锅法合成N-呋喃酮基磺酰腙类化合物

One-Pot Synthesis ofN-Furanonyl Sulfonyl Hydrazone Compounds

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