Brønsted Base-Catalyzed Assembly of Sulfochromeno[4,3-b]-pyrrolidines via Michael-Mannich-SuFEx Tandem Reaction of o-Hydroxy Schiff Bases and Vinylsulfonyl Fluorides

doi:10.6023/cjoc202410010

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (7): 2552-2565.DOI: 10.6023/cjoc202410010 Previous Articles Next Articles

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Brønsted碱促进的o-羟基席夫碱与乙烯基磺酰氟通过Michael-Mannich-SuFEx串联反应构建磺基色烯并[4,3‑b]吡咯烷化合物

张放^a, 谢佩^a, 张启超^a, 武磊芳^b^,^*(), 何林^a, 杜广芬^a^,^*()

^a 石河子大学化学化工学院化工绿色过程省部共建国家重点实验室培育基地新疆石河子 832000
^b 石河子大学分析测试中心新疆石河子 832000

收稿日期:2024-11-27 修回日期:2024-12-11 发布日期:2025-01-17
基金资助:
新疆天山英才计划(2023TSYCCX0122); 石河子大学国际合作(GJHZ202204); 石河子大学引导(2022ZD021); 石河子大学引导(2022ZD067)

Brønsted Base-Catalyzed Assembly of Sulfochromeno[4,3-b]-pyrrolidines via Michael-Mannich-SuFEx Tandem Reaction of o-Hydroxy Schiff Bases and Vinylsulfonyl Fluorides

Fang Zhang^a, Pei Xie^a, Qichao Zhang^a, Leifang Wu^b^,^*(), Lin He^a, Guangfen Du^a^,^*()

^a School of Chemistry and Chemical Engineering, Shihezi University/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi, Xinjiang 832000
^b Analysis and Testing Center of Shihezi University, Shihezi, Xinjiang 832000

Received:2024-11-27 Revised:2024-12-11 Published:2025-01-17
Contact: *E-mail: duguangfen@shzu.edu.cn; 719591324@qq.com
Supported by:
Tianshan Talent Research Project of Xinjiang(2023TSYCCX0122); International Cooperation Project of Shihezi University(GJHZ202204); Guidance Project of Shihezi University(2022ZD021); Guidance Project of Shihezi University(2022ZD067)

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Abstract

A method for the efficient synthesis of sulfochromeno[4,3-b]pyrrole compounds through the Michael-Mannich- SuFEx tandem reaction under mild conditions is introduced. Using o-hydroxy Schiff base and 2-substituted vinylsulfonyl fluoride as substrates, the yield was as high as 99%, the diastereoselectivity exceeded 95:5, and a total of 37 target compounds were synthesized. ¹⁹F NMR monitoring and density functional theory (DFT) studies showed that the reaction went through three stages of Michael-Mannich-SuFEx. Antibacterial tests show that some compounds have inhibitory effects on Cytospora chrysosperma.

Key words: SuFEx chemsitry, vinylsulfonyl fluoride, o-hydroxy Schiff base, sulfochromeno[4,3-b]pyrrolidines

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Fang Zhang, Pei Xie, Qichao Zhang, Leifang Wu, Lin He, Guangfen Du. Brønsted Base-Catalyzed Assembly of Sulfochromeno[4,3-b]-pyrrolidines via Michael-Mannich-SuFEx Tandem Reaction of o-Hydroxy Schiff Bases and Vinylsulfonyl Fluorides[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2552-2565.

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Fig. & Tab. 13

References 12

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[14]	CCDC 2353272 (3j) and 2380699 (3am) contain the supplementary crystallographic data for this paper.
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Entry	Ar¹	Hirshfeld charge	Yield^b/%	dr^c
1	Ph	0.0737	N.D.^d	—
2	4-MeOC₆H₄	0.0733	N.D.^d	—
3	4-CF₃C₆H₄	0.0755	<10%	—
4	4-CNC₆H₄	0.0763	<10%	—
5	4-NO₂C₆H₄	0.0767	56	83∶17
6	2,4,6-F₃C₆H₂	0.0698	N.D.^d	—
7	2,3,4,5,6-F₅C₆	0.0738	N.D.^d	—
8	3,5-(CF₃)₂C₆H₃	0.0774	Complex	—

Entry	Ar¹	Hirshfeld charge	Yield^b/%	dr^c
1	Ph	0.0737	N.D.^d	—
2	4-MeOC₆H₄	0.0733	N.D.^d	—
3	4-CF₃C₆H₄	0.0755	<10%	—
4	4-CNC₆H₄	0.0763	<10%	—
5	4-NO₂C₆H₄	0.0767	56	83∶17
6	2,4,6-F₃C₆H₂	0.0698	N.D.^d	—
7	2,3,4,5,6-F₅C₆	0.0738	N.D.^d	—
8	3,5-(CF₃)₂C₆H₃	0.0774	Complex	—

Entry	Base	Solvent	Yield^b/%	dr^c
1	Et₃N	MeCN	56	83∶17
2	DIPEA	MeCN	42	92∶8
3	DBU	MeCN	92	94∶6
4	DBN	MeCN	89	91∶9
5	Cs₂CO₃	MeCN	31	90∶10
6	DBU	DMSO	99 (99)^d	>95∶5
7	DBU	DMF	94	>95∶5
8	DBU	DCM	41	85∶15
9	DBU	THF	57	93∶7
10	DBU	MeOH	21	51∶49
11	DBU	EtOH	34	56∶44
12	DBU	H₂O	Trace	—
13^e	DBU	DMSO	66	>95∶5
14^f	—	DMSO	N.D.^j	—
15^g	DBU	DMSO	40	>95∶5
16^h	DBU	DMSO	92	>95∶5
17ⁱ	—	DMSO	N.D.^j	—

Entry	Base	Solvent	Yield^b/%	dr^c
1	Et₃N	MeCN	56	83∶17
2	DIPEA	MeCN	42	92∶8
3	DBU	MeCN	92	94∶6
4	DBN	MeCN	89	91∶9
5	Cs₂CO₃	MeCN	31	90∶10
6	DBU	DMSO	99 (99)^d	>95∶5
7	DBU	DMF	94	>95∶5
8	DBU	DCM	41	85∶15
9	DBU	THF	57	93∶7
10	DBU	MeOH	21	51∶49
11	DBU	EtOH	34	56∶44
12	DBU	H₂O	Trace	—
13^e	DBU	DMSO	66	>95∶5
14^f	—	DMSO	N.D.^j	—
15^g	DBU	DMSO	40	>95∶5
16^h	DBU	DMSO	92	>95∶5
17ⁱ	—	DMSO	N.D.^j	—

Compd.	Inhibitory rate±SD/%	Compd.	Inhibitory rate±SD/%
3a	65.1±2.3	3l	43.1±7.1
3b	60.9±6.4	3m	45.3±3.2
3c	48.3±2.3	3n	61.4±4.1
3d	58.9±2.3	3o	77.0±2.6
3e	64.5±1.8	3p	45.2±2.3
3f	76.8±4.7	3q	40.4±7.7
3g	63.5±7.7	3r	23.3±3.2
3h	58.4±3.8	3s	53.3±3.8
3i	59.1±4.0	3t	31.4±3.5
3j	48.2±3.2	3u	51.8±0.8
3k	53.8±1.5	3v	50.2±4.0

Brønsted碱促进的o-羟基席夫碱与乙烯基磺酰氟通过Michael-Mannich-SuFEx串联反应构建磺基色烯并[4,3‑b]吡咯烷化合物

Brønsted Base-Catalyzed Assembly of Sulfochromeno[4,3-b]-pyrrolidines via Michael-Mannich-SuFEx Tandem Reaction of o-Hydroxy Schiff Bases and Vinylsulfonyl Fluorides

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