Visible-Light-Mediated C3-H Acetalation of Quinoxalin-2(1H)-ones

doi:10.6023/cjoc202209013

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (12): 4315-4322.DOI: 10.6023/cjoc202209013 Previous Articles Next Articles

Special Issue: 自由基化学专辑

ARTICLES

可见光介导喹喔啉-2(1H)-酮C3-H缩醛化反应

张孟琪^a, 南光明^a^,^*(), 赵晓辉^b, 魏伟^c^,^*()

a 伊犁师范大学化学与环境科学学院新疆普通高等学校天然产物化学与应用重点实验室新疆伊宁 835000
b 中国科学院西北高原生物研究所中国科学院藏药研究重点实验室西宁 810008
c 曲阜师范大学化学与化工学院山东曲阜 273165

收稿日期:2022-09-11 修回日期:2022-10-03 发布日期:2022-10-24
通讯作者: 南光明, 魏伟
基金资助:
新疆普通高等学校天然产物化学与应用重点实验室基金(2022YSHXZD01)

Visible-Light-Mediated C3-H Acetalation of Quinoxalin-2(1H)-ones

Mengqi Zhang^a, Guangming Nan^a(), Xiaohui Zhao^b, Wei Wei^c()

a University and College Key Laboratory of Natural Product Chemistry and Application in Xinjiang, School of Chemistry and Environmental Science, Yili Normal University, Yining, Xinjiang 835000
b CAS Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008
c School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165

Received:2022-09-11 Revised:2022-10-03 Published:2022-10-24
Contact: Guangming Nan, Wei Wei
Supported by:
Foundation of University and College Key Laboratory of Natural Product Chemistry and Application in Xinjiang(2022YSHXZD01)

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Abstract

Visible-light-mediated 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) catalyzed decarboxylic acetalation of quinoxalin-2(1H)-ones with glyoxylic acid acetalde to access 3-acetal quinoxalin-2(1H)-ones has been reported. This reaction provides a green and efficient approach to construct a series of 3-acetal quinoxalin-2(1H)-ones by using of air as the oxidant at room temperature, which has the advantages of clean source of energy, mild conditions, metal-free and green oxidant. Radical trapping experiment and fluorescence quenching experiments showed that visible-light promoted radical reaction process was involved in this reaction system.

Key words: visible-light, quinoxalin-2(1H)-ones, decarboxylic acetalation, radical reaction

Cite this article

Mengqi Zhang, Guangming Nan, Xiaohui Zhao, Wei Wei. Visible-Light-Mediated C3-H Acetalation of Quinoxalin-2(1H)-ones[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4315-4322.

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References 18

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Entry	Photocatalyst (x mol%)	Base	Solvent	Yield^b/%
1	Rose Bengal (2)	Na₂CO₃	DMSO	50
2	Eosin B (2)	Na₂CO₃	DMSO	25
3	Rhodamine B (2)	Na₂CO₃	DMSO	30
4	Acridine Red (2)	Na₂CO₃	DMSO	51
5	Na₂-eosin Y (2)	Na₂CO₃	DMSO	31
6	Eosin Y (2)	Na₂CO₃	DMSO	30
7	4CzIPN (2)	Na₂CO₃	DMSO	69
8	4CzIPN (2)	Cs₂CO₃	DMSO	70
9	4CzIPN (2)	K₃PO₄	DMSO	45
10	4CzIPN (2)	NaHCO₃	DMSO	48
11	4CzIPN (2)	KOH	DMSO	40
12	4CzIPN (2)	DABCO	DMSO	61
13	4CzIPN (2)	DBU	DMSO	84
14	4CzIPN (2)	—	DMSO	0
15	4CzIPN (1)	DBU	DMSO	32
16	4CzIPN (5)	DBU	DMSO	63
17	—	DBU	DMSO	Trace
18	4CzIPN (2)	DBU	DMF	61
19	4CzIPN (2)	DBU	DCE	16
20	4CzIPN (2)	DBU	CH₂Cl₂	14
21	4CzIPN (2)	DBU	DME	8
22	4CzIPN (2)	DBU	1,4-Dioxane	Trace
23	4CzIPN (2)	DBU	THF	Trace
24	4CzIPN (2)	DBU	H₂O	0
25	4CzIPN (2)	DBU	DMSO	68^c
26	4CzIPN (2)	DBU	DMSO	51^d
27	4CzIPN (2)	DBU	DMSO	0^e

Entry	Photocatalyst (x mol%)	Base	Solvent	Yield^b/%
1	Rose Bengal (2)	Na₂CO₃	DMSO	50
2	Eosin B (2)	Na₂CO₃	DMSO	25
3	Rhodamine B (2)	Na₂CO₃	DMSO	30
4	Acridine Red (2)	Na₂CO₃	DMSO	51
5	Na₂-eosin Y (2)	Na₂CO₃	DMSO	31
6	Eosin Y (2)	Na₂CO₃	DMSO	30
7	4CzIPN (2)	Na₂CO₃	DMSO	69
8	4CzIPN (2)	Cs₂CO₃	DMSO	70
9	4CzIPN (2)	K₃PO₄	DMSO	45
10	4CzIPN (2)	NaHCO₃	DMSO	48
11	4CzIPN (2)	KOH	DMSO	40
12	4CzIPN (2)	DABCO	DMSO	61
13	4CzIPN (2)	DBU	DMSO	84
14	4CzIPN (2)	—	DMSO	0
15	4CzIPN (1)	DBU	DMSO	32
16	4CzIPN (5)	DBU	DMSO	63
17	—	DBU	DMSO	Trace
18	4CzIPN (2)	DBU	DMF	61
19	4CzIPN (2)	DBU	DCE	16
20	4CzIPN (2)	DBU	CH₂Cl₂	14
21	4CzIPN (2)	DBU	DME	8
22	4CzIPN (2)	DBU	1,4-Dioxane	Trace
23	4CzIPN (2)	DBU	THF	Trace
24	4CzIPN (2)	DBU	H₂O	0
25	4CzIPN (2)	DBU	DMSO	68^c
26	4CzIPN (2)	DBU	DMSO	51^d
27	4CzIPN (2)	DBU	DMSO	0^e

可见光介导喹喔啉-2(1H)-酮C3-H缩醛化反应

Visible-Light-Mediated C3-H Acetalation of Quinoxalin-2(1H)-ones

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