N-苯基丙烯酰胺与草氨酸衍生物的脱羧氨甲酰化反应研究

doi:10.6023/cjoc202105025

摘要/Abstract

报道了一种银催化的N-苯基丙烯酰胺与N-取代草氨酸类衍生物的脱羧氨甲酰化反应, 通过分子间的氨甲酰自由基加成/环化过程, 能够以良好的产率制备一系列3,3-二取代的氨甲酰官能化的吲哚酮类化合物. 该反应具有广泛的官能团兼容性和良好的底物适用范围.

关键词: 氨甲酰化, 吲哚酮, 自由基加成环化

A silver catalyzed decaroxylative amidation of N-arylacrylamides with oxamic acids has been developed. This cascade reaction is an effective way to synthesize various 3,3-disubstitued amide functionalized oxindoles through a sequence of intermolecular carbamoyl radical addition and cyclization in moderate to good yields. This reaction allows a broad range of substrates as well as good functional group compatibility.

Key words: carbamoylation, oxindoles, radical addition cyclization

引用此文

高启升, 荆祺, 陈阳, 孙京, 周明东. N-苯基丙烯酰胺与草氨酸衍生物的脱羧氨甲酰化反应研究[J]. 有机化学, 2022, 42(1): 257-265.

Qisheng Gao, Qi Jing, Yang Chen, Jing Sun, Mingdong Zhou. Decarboxylative Amidation of Acrylamides with Oxamic Acids[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 257-265.

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参考文献 14

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Entry	Catalyst (mol%)	Oxidant (equiv.)	Solvent	Yield^b/%
1	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN	28
2	AgNO₃ (10)	K₂S₂O₈ (2)	H₂O	46
3	AgNO₃ (10)	K₂S₂O₈ (2)	THF	<5
4	AgNO₃ (10)	K₂S₂O₈ (2)	DCM	<5
5	AgNO₃ (10)	K₂S₂O₈ (2)	DMSO	<5
6	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃OH	15
7	AgNO₃ (10)	K₂S₂O₈ (2)	DMF	31
8	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=3∶1)	46
9	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶3)	54
10	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	60
11	AgOAc (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	64
12	Ag₂O (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	60
13	Ag₂CO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	76
14	CuBr (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	Trace
15	Cu(OAc)₂ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	Trace
16	Ag₂CO₃ (10)	Na₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	48
17	Ag₂CO₃ (10)	(NH₄)₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	10
18	Ag₂CO₃ (10)	TBHP (2)	CH₃CN/H₂O (V∶V=1∶1)	nr
19	Ag₂CO₃ (10)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	86
20	Ag₂CO₃ (10)	K₂S₂O₈ (1)	CH₃CN/H₂O (V∶V=1∶1)	72
21	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	85 (82)^c
22^d	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	76
23^e	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	76
24^f	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	39
25	—	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	54
26	Ag₂CO₃ (5)	—	CH₃CN/H₂O (V∶V=1∶1)	Trace

Entry	Catalyst (mol%)	Oxidant (equiv.)	Solvent	Yield^b/%
1	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN	28
2	AgNO₃ (10)	K₂S₂O₈ (2)	H₂O	46
3	AgNO₃ (10)	K₂S₂O₈ (2)	THF	<5
4	AgNO₃ (10)	K₂S₂O₈ (2)	DCM	<5
5	AgNO₃ (10)	K₂S₂O₈ (2)	DMSO	<5
6	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃OH	15
7	AgNO₃ (10)	K₂S₂O₈ (2)	DMF	31
8	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=3∶1)	46
9	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶3)	54
10	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	60
11	AgOAc (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	64
12	Ag₂O (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	60
13	Ag₂CO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	76
14	CuBr (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	Trace
15	Cu(OAc)₂ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	Trace
16	Ag₂CO₃ (10)	Na₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	48
17	Ag₂CO₃ (10)	(NH₄)₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	10
18	Ag₂CO₃ (10)	TBHP (2)	CH₃CN/H₂O (V∶V=1∶1)	nr
19	Ag₂CO₃ (10)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	86
20	Ag₂CO₃ (10)	K₂S₂O₈ (1)	CH₃CN/H₂O (V∶V=1∶1)	72
21	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	85 (82)^c
22^d	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	76
23^e	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	76
24^f	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	39
25	—	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	54
26	Ag₂CO₃ (5)	—	CH₃CN/H₂O (V∶V=1∶1)	Trace

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