Metal-Free 1,8-Diazabicyclo(5.4.0)-undec-7-ene Mediated Synthesis of α-Acetal Amides through Reaction of Glyoxylic Acid Acetalde with Aryl Isothiocyanates

doi:10.6023/cjoc202403029

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2216-2222.DOI: 10.6023/cjoc202403029 Previous Articles Next Articles

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非金属1,8-二氮杂双环[5.4.0]十一碳-7-烯介导下乙缩醛酸与异硫氰酸酯反应合成α-缩醛基酰胺

丁柔^a, 石思雨^a, 马超^a, 魏伟^a^,^b^,^*(), 吕玉芬^a^,^*()

a 曲阜师范大学化学与化工学院山东曲阜 273165
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

收稿日期:2024-03-20 修回日期:2024-04-08 发布日期:2024-04-30
基金资助:
山东省自然科学基金(ZR2021MB065); 青海省科技国际合作专项(2022-HZ-813)

Metal-Free 1,8-Diazabicyclo(5.4.0)-undec-7-ene Mediated Synthesis of α-Acetal Amides through Reaction of Glyoxylic Acid Acetalde with Aryl Isothiocyanates

Rou Ding^a, Siyu Shi^a, Chao Ma^a, Wei Wei^a^,^b(), Yufen Lü^a()

a School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165
b CAS Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008

Received:2024-03-20 Revised:2024-04-08 Published:2024-04-30
Contact: * E-mail: weiweiqfnu@163.com;yufenlv06@163.com
Supported by:
Natural Science Foundation of Shandong Province(ZR2021MB065); Science and Technology International Cooperation Project of Qinghai Province(2022-HZ-813)

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Abstract

Metal-free condensation reaction of glyoxylic acid acetalde with aryl isothiocyanates leading to α-acetal amides has been reported. The present protocol, which simply utilizes 1,8-diazabicyclo(5.4.0)-undec-7-ene (DBU) as base, provides a green and efficient approach to construct a series of α-acetal amides in the absence of metal catalysts and stoichiometric amounts of coupling reagents.

Key words: metal-free, α-acetalamide, glyoxylic acid, aryl isothiocyanate

Cite this article

Rou Ding, Siyu Shi, Chao Ma, Wei Wei, Yufen Lü. Metal-Free 1,8-Diazabicyclo(5.4.0)-undec-7-ene Mediated Synthesis of α-Acetal Amides through Reaction of Glyoxylic Acid Acetalde with Aryl Isothiocyanates[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2216-2222.

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Fig. & Tab. 6

References 17

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Entry	Base (x/mol%)	Solvent	Yield^b/%
1	Cs₂CO₃(120)	DMSO	60
2	Na₂CO₃ (120)	DMSO	64
3	K₃PO₄(120)	DMSO	72
4	NaHCO₃(120)	DMSO	32
5	KOH (120)	DMSO	74
6	DABCO (120)	DMSO	40
7	DBU (120)	DMSO	76
8	DBU (120)	DMF	63
9	DBU (120)	DME	10
10	DBU (120)	THF	20
11	DBU (120)	1,4-Dioxane	25
12	DBU (120)	CH₃CN	49
13	DBU (120)	EtOAc	34
14	DBU (120)	DCE	30
15	DBU (120)	Toluene	32
16	DBU (120)	H₂O	0
17	DBU (20)	DMSO	26
18	DBU (40)	DMSO	48
19	DBU (60)	DMSO	53
20	DBU (80)	DMSO	68
21	DBU (100)	DMSO	79
22	DBU (150)	DMSO	85
23	DBU (200)	DMSO	89
24	—	DMSO	0
25	DBU (200)	DMSO	85^c
26	DBU (200)	DMSO	84^d

Entry	Base (x/mol%)	Solvent	Yield^b/%
1	Cs₂CO₃(120)	DMSO	60
2	Na₂CO₃ (120)	DMSO	64
3	K₃PO₄(120)	DMSO	72
4	NaHCO₃(120)	DMSO	32
5	KOH (120)	DMSO	74
6	DABCO (120)	DMSO	40
7	DBU (120)	DMSO	76
8	DBU (120)	DMF	63
9	DBU (120)	DME	10
10	DBU (120)	THF	20
11	DBU (120)	1,4-Dioxane	25
12	DBU (120)	CH₃CN	49
13	DBU (120)	EtOAc	34
14	DBU (120)	DCE	30
15	DBU (120)	Toluene	32
16	DBU (120)	H₂O	0
17	DBU (20)	DMSO	26
18	DBU (40)	DMSO	48
19	DBU (60)	DMSO	53
20	DBU (80)	DMSO	68
21	DBU (100)	DMSO	79
22	DBU (150)	DMSO	85
23	DBU (200)	DMSO	89
24	—	DMSO	0
25	DBU (200)	DMSO	85^c
26	DBU (200)	DMSO	84^d

非金属1,8-二氮杂双环[5.4.0]十一碳-7-烯介导下乙缩醛酸与异硫氰酸酯反应合成α-缩醛基酰胺

Metal-Free 1,8-Diazabicyclo(5.4.0)-undec-7-ene Mediated Synthesis of α-Acetal Amides through Reaction of Glyoxylic Acid Acetalde with Aryl Isothiocyanates

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