Silver-Mediated Trifluoromethylthiolation-Cyclization-Hydrolysis: Access to F3CS-Containing Quinolinones

doi:10.6023/cjoc202203001

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 2089-2097.DOI: 10.6023/cjoc202203001 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑

ARTICLES

银催化三氟甲硫基化-环化-水解: 含F₃CS基喹啉酮合成

李猛^a, 孙凯^b^,^*()

^a淄博职业学院制药与生物工程系山东淄博 255300
^b烟台大学化学化工学院山东烟台 264005

收稿日期:2022-03-01 修回日期:2022-04-03 发布日期:2022-08-09
通讯作者: 孙凯
基金资助:
国家自然科学基金(21801007); 武陵山民族药解析与创制湖南省工程实验室开放基金(Hgxy2103)

Silver-Mediated Trifluoromethylthiolation-Cyclization-Hydrolysis: Access to F₃CS-Containing Quinolinones

Meng Li^a, Kai Sun^b()

^aDepartment of Pharmacy and Biotechnology, Zibo Vocational Institute, Zibo, Shandong 255300
^bCollege of Chemistry and Chemical Engineering, Yantai University, Yantai, Shandong 264005

Received:2022-03-01 Revised:2022-04-03 Published:2022-08-09
Contact: Kai Sun
Supported by:
National Natural Science Foundation of China(21801007); Aid Program from Hunan Engineering Laboratory for Analyse and Drugs Development of Ethnomedicine in Wunlin Mountains(Hgxy2103)

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Abstract

Herein, a practical formal silver-mediated trifluoromethylthiolation cyclization hydrolysis protocol was developed with the cyano group as a radical acceptor. Various structurally diverse F₃CS-substituted quinolinones were obtained in moderate to high yields. Easy scale-up operation and the potential for product derivatization make this method attractive for the preparation of other valuable F₃CS-containing N-heterocycles. Mechanistic studies suggest that the catalytic system involves a radical pathway and H₂O plays an indispensable role in the hydrolysis process.

Key words: trifluoromethylthiolation, N-heterocycles, cyclization, radical, derivatization

Cite this article

Meng Li, Kai Sun. Silver-Mediated Trifluoromethylthiolation-Cyclization-Hydrolysis: Access to F₃CS-Containing Quinolinones[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2089-2097.

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Fig. & Tab. 6

References 16

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Entry	Solvent	Oxidant	T/℃	Yield^b/%
1	DMSO	K₂S₂O₈	80	35
2	V(DMSO)∶V(H₂O)=4∶1	K₂S₂O₈	80	59
3	V(DMSO)∶V(H₂O)=2∶1	K₂S₂O₈	80	33
4	V(DMSO)∶V(H₂O)=1∶1	K₂S₂O₈	80	33
5	V(CH₃CN)∶V(H₂O)=4∶1	K₂S₂O₈	80	55
6	V(DMF)∶V(H₂O)=4∶1	K₂S₂O₈	80	46
7	V(acetone)∶V(H₂O)=4∶1	K₂S₂O₈	80	57
8	V(dioxane)∶V(H₂O)=4∶1	K₂S₂O₈	80	36
9	V(EtOAc)∶V(H₂O)=4∶1	K₂S₂O₈	80	0
10	V(DMSO)∶V(H₂O)=4∶1	K₂S₂O₈	60	25
11	V(DMSO)∶V(H₂O)=4∶1	K₂S₂O₈	100	68
12	V(DMSO)∶V(H₂O)=4∶1	K₂S₂O₈	120	85
13	V(DMSO)∶V(H₂O)=4∶1	Na₂S₂O₈	120	71
14	V(DMSO)∶V(H₂O)=4∶1	(NH₄)₂S₂O₈	120	40
15	V(DMSO)∶V(H₂O)=4∶1	PhI(OAc)₂	120	Trace
16	V(DMSO)∶V(H₂O)=4∶1	TBHP	120	0
17	V(DMSO)∶V(H₂O)=4∶1	Selectfluor	120	0
18	V(DMSO)∶V(H₂O)=4∶1	Oxone	120	0

Entry	Solvent	Oxidant	T/℃	Yield^b/%
1	DMSO	K₂S₂O₈	80	35
2	V(DMSO)∶V(H₂O)=4∶1	K₂S₂O₈	80	59
3	V(DMSO)∶V(H₂O)=2∶1	K₂S₂O₈	80	33
4	V(DMSO)∶V(H₂O)=1∶1	K₂S₂O₈	80	33
5	V(CH₃CN)∶V(H₂O)=4∶1	K₂S₂O₈	80	55
6	V(DMF)∶V(H₂O)=4∶1	K₂S₂O₈	80	46
7	V(acetone)∶V(H₂O)=4∶1	K₂S₂O₈	80	57
8	V(dioxane)∶V(H₂O)=4∶1	K₂S₂O₈	80	36
9	V(EtOAc)∶V(H₂O)=4∶1	K₂S₂O₈	80	0
10	V(DMSO)∶V(H₂O)=4∶1	K₂S₂O₈	60	25
11	V(DMSO)∶V(H₂O)=4∶1	K₂S₂O₈	100	68
12	V(DMSO)∶V(H₂O)=4∶1	K₂S₂O₈	120	85
13	V(DMSO)∶V(H₂O)=4∶1	Na₂S₂O₈	120	71
14	V(DMSO)∶V(H₂O)=4∶1	(NH₄)₂S₂O₈	120	40
15	V(DMSO)∶V(H₂O)=4∶1	PhI(OAc)₂	120	Trace
16	V(DMSO)∶V(H₂O)=4∶1	TBHP	120	0
17	V(DMSO)∶V(H₂O)=4∶1	Selectfluor	120	0
18	V(DMSO)∶V(H₂O)=4∶1	Oxone	120	0

银催化三氟甲硫基化-环化-水解: 含F₃CS基喹啉酮合成

Silver-Mediated Trifluoromethylthiolation-Cyclization-Hydrolysis: Access to F₃CS-Containing Quinolinones

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银催化三氟甲硫基化-环化-水解: 含F3CS基喹啉酮合成