Direct Synthesis of 3-Sulfonylquinolines from N-Propargylanilines with Sulfonyl Chlorides

doi:10.6023/cjoc202203055

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2527-2534.DOI: 10.6023/cjoc202203055 Previous Articles Next Articles

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由N-(2-丙炔基)苯胺和磺酰氯直接合成3-砜基喹啉

王苛莉^a, 黄静^a, 刘伟^b, 伍智林^a, 于贤勇^b, 蒋俊^a^,^*(), 何卫民^a^,^*()

a 南华大学化学化工学院湖南衡阳 411201
b 湖南科技大学理论有机化学与功能分子教育部重点实验室湖南湘潭 411201

收稿日期:2022-03-28 修回日期:2022-04-26 发布日期:2022-05-06
通讯作者: 蒋俊, 何卫民
基金资助:
湖南省教育厅科学研究项目(19C0783); 湖南省科技创新计划项目(2021RC5028)

Direct Synthesis of 3-Sulfonylquinolines from N-Propargylanilines with Sulfonyl Chlorides

Keli Wang^a, Jing Huang^a, Wei Liu^b, Zhilin Wu^a, Xianyong Yu^b, Jun Jiang^a(), Weimin He^a()

a School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001
b Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology, Xiangtan, Hunan 411201

Received:2022-03-28 Revised:2022-04-26 Published:2022-05-06
Contact: Jun Jiang, Weimin He
Supported by:
Scientific Research Fund of Hunan Provincial Education Department(19C0783); Science and Technology Innovation Program of Hunan Province(2021RC5028)

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Abstract

3-Sulfonylquinolines broadly exist in plenty of bioactive molecules and synthetic pharmaceuticals. Herein, an efficient and facile method for direct synthesizing various 3-sulfonylquinolines through one-pot sequential hydrazination/sulfonylation/cyclization reaction from N-propargylanilines and sulfonyl chlorides under mild reaction conditions is reported. This procedure not only can be performed on a gram scale but also be applicable to prepare marketed pharmaceutical derivative.

Key words: 3-sulfonylquinolines, N-propargylanilines, sulfonyl chlorides, one pot, cyclization reaction

Cite this article

Keli Wang, Jing Huang, Wei Liu, Zhilin Wu, Xianyong Yu, Jun Jiang, Weimin He. Direct Synthesis of 3-Sulfonylquinolines from N-Propargylanilines with Sulfonyl Chlorides[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2527-2534.

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References 12

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Entry	Oxidant	Base	Solvent	Temp./℃	Yield^b/%
1	TBHP	K₂CO₃	DCM	80	58
2	DTBP	K₂CO₃	DCM	80	11
3	BPO	K₂CO₃	DCM	80	6
4	H₂O₂	K₂CO₃	DCM	80	Trace
5	PhI(OAc)₂	K₂CO₃	DCM	80	8
6	K₂S₂O₈	K₂CO₃	DCM	80	14
7	TBHP	Na₂CO₃	DCM	80	44
8	TBHP	Cs₂CO₃	DCM	80	90
9	TBHP	Et₃N	DCM	80	55
10	TBHP	Pyridine	DCM	80	43
11	TBHP	DABCO	DCM	80	22
12	TBHP	Cs₂CO₃	DCE	80	69
13	TBHP	Cs₂CO₃	MeCN	80	82
14	TBHP	Cs₂CO₃	EtOH	80	9
15	TBHP	Cs₂CO₃	EtOAc	80	45
16	TBHP	Cs₂CO₃	THF	80	35
17	TBHP	Cs₂CO₃	DCM	90	89
18	TBHP	Cs₂CO₃	DCM	70	62
19	—	Cs₂CO₃	DCM	80	—
20	TBHP	—	DCM	80	15
21^c	TBHP	Cs₂CO₃	DCM	80	—
22^d	TBHP	Cs₂CO₃	DCM	80	84
22^d	TBHP	Cs₂CO₃	DCM	80	55

Entry	Oxidant	Base	Solvent	Temp./℃	Yield^b/%
1	TBHP	K₂CO₃	DCM	80	58
2	DTBP	K₂CO₃	DCM	80	11
3	BPO	K₂CO₃	DCM	80	6
4	H₂O₂	K₂CO₃	DCM	80	Trace
5	PhI(OAc)₂	K₂CO₃	DCM	80	8
6	K₂S₂O₈	K₂CO₃	DCM	80	14
7	TBHP	Na₂CO₃	DCM	80	44
8	TBHP	Cs₂CO₃	DCM	80	90
9	TBHP	Et₃N	DCM	80	55
10	TBHP	Pyridine	DCM	80	43
11	TBHP	DABCO	DCM	80	22
12	TBHP	Cs₂CO₃	DCE	80	69
13	TBHP	Cs₂CO₃	MeCN	80	82
14	TBHP	Cs₂CO₃	EtOH	80	9
15	TBHP	Cs₂CO₃	EtOAc	80	45
16	TBHP	Cs₂CO₃	THF	80	35
17	TBHP	Cs₂CO₃	DCM	90	89
18	TBHP	Cs₂CO₃	DCM	70	62
19	—	Cs₂CO₃	DCM	80	—
20	TBHP	—	DCM	80	15
21^c	TBHP	Cs₂CO₃	DCM	80	—
22^d	TBHP	Cs₂CO₃	DCM	80	84
22^d	TBHP	Cs₂CO₃	DCM	80	55

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由N-(2-丙炔基)苯胺和磺酰氯直接合成3-砜基喹啉

Direct Synthesis of 3-Sulfonylquinolines from N-Propargylanilines with Sulfonyl Chlorides

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