Synthesis of α-Carbolinone Compounds Based on Tandem Cyclization Reaction of 2-Nitrochalcone and Ethyl Isocyanoacetate

doi:10.6023/cjoc202409014

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (6): 2163-2170.DOI: 10.6023/cjoc202409014 Previous Articles Next Articles

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基于2-硝基查尔酮与异氰基乙酸乙酯的串联环化反应合成α-咔啉酮类化合物

盛馨瑶, 李鑫鑫, 邢潇^b, 潘玲^a, 刘群, 李亦菲^a^,^*()

^a 东北师范大学化学学院长春 130024
^b 长春市食品药品检验中心长春 130012

收稿日期:2024-12-10 修回日期:2025-01-07 发布日期:2025-01-17
通讯作者: 李亦菲
基金资助:
吉林省自然科学基金(20220101066JC); 吉林省自然科学基金(20220402046GH); 吉林省教育厅科学研究(JJKH20250313BS)

Synthesis of α-Carbolinone Compounds Based on Tandem Cyclization Reaction of 2-Nitrochalcone and Ethyl Isocyanoacetate

Xinyao Sheng, Xinxin Li, Xiao Xing^b, Ling Pan^a, Qun Liu, Yifei Li^a^,^*()

^a School of Chemistry, Northeast Normal University, Changchun 130024
^b Changchun Food and Drug Control, Changchun 130012

Received:2024-12-10 Revised:2025-01-07 Published:2025-01-17
Contact: Yifei Li
Supported by:
Natural Science Foundation of Jilin Province(20220101066JC); Natural Science Foundation of Jilin Province(20220402046GH); Research Projects from Education Department of Jilin Province(JJKH20250313BS); Natural Science Foundation of Jilin Province(20220101066 JC)

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Abstract

α-Carbolinone compounds are widely present in various natural products and drug active molecules, and the synthesis methods have important research significance and application value. A novel tandem cycloaddition reaction based on 2-nitrochalcone and ethyl isocyanoacetate has been discovered, which can be used for efficient synthesis of α-carbolinone compounds. The synthesis process achieved two nitrogen heterocyclic systems, and the formation and transformation of multiple chemical bonds through a one-step reaction. Moreover, the reduction cyclization process did not use external reductant. The reaction process is simple to operate, the reaction materials are cheap and easy to obtain, and the reaction condition is green and mild. In conclusion, it is an effective and practical method for the synthesis of carbolinones.

Key words: α-carbolinone, 2-nitrochalcone, ethyl isocyanoacetate, tandem cyclization reaction

Cite this article

Xinyao Sheng, Xinxin Li, Xiao Xing, Ling Pan, Qun Liu, Yifei Li. Synthesis of α-Carbolinone Compounds Based on Tandem Cyclization Reaction of 2-Nitrochalcone and Ethyl Isocyanoacetate[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2163-2170.

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References 24

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Entry	1a∶2	Catalyst (equiv.)	Solvent	Temp./ ℃	Time/ h	Yield^b/ %
1	1∶2	K₂CO₃ (1.0)	EtOH	120	5	39^c
2	1∶2	CsCO₃ (1.0)	EtOH	120	5	40^d
3	1∶2	NaOH (1.0)	EtOH	120	5	61
4	1∶2	DBU (1.0)	EtOH	120	5	65
5	1∶2	DBU (0.5)	EtOH	120	5	49^e
6	1∶2	DBU (2.0)	EtOH	120	5	62
7	1∶1.2	DBU (1.0)	EtOH	120	5	36^f
8	1∶1.5	DBU (1.0)	EtOH	120	5	43
9	1.2∶1	DBU (1.0)	EtOH	120	5	50
10	1.5∶1	DBU (1.0)	EtOH	120	5	71
11	2∶1	DBU (1.0)	EtOH	120	5	55
12	1.5∶1	DBU (1.0)	THF	120	5	58
13	1.5∶1	DBU (1.0)	CHCl₃	120	5	51
14	1.5∶1	DBU (1.0)	EtOAc	120	5	Trace
15	1.5∶1	DBU (1.0)	Toluene	120	5	30
16	1.5﹕1	DBU (1.0)	CH₃CN	120	5	42
17	1.5∶1	DBU (1.0)	Dry EtOH	120 (N₂)	5	77
18	1.5∶1	DBU (1.0)	Dry EtOH	100 (N₂)	5	70
19	1.5∶1	DBU (1.0)	Dry EtOH	130 (N₂)	5	75
20	1.5∶1	DBU (1.0)	Dry EtOH	120 (N₂)	4	81
21	1.5∶1	DBU (1.0)	Dry EtOH	120 (N₂)	6	72

Entry	1a∶2	Catalyst (equiv.)	Solvent	Temp./ ℃	Time/ h	Yield^b/ %
1	1∶2	K₂CO₃ (1.0)	EtOH	120	5	39^c
2	1∶2	CsCO₃ (1.0)	EtOH	120	5	40^d
3	1∶2	NaOH (1.0)	EtOH	120	5	61
4	1∶2	DBU (1.0)	EtOH	120	5	65
5	1∶2	DBU (0.5)	EtOH	120	5	49^e
6	1∶2	DBU (2.0)	EtOH	120	5	62
7	1∶1.2	DBU (1.0)	EtOH	120	5	36^f
8	1∶1.5	DBU (1.0)	EtOH	120	5	43
9	1.2∶1	DBU (1.0)	EtOH	120	5	50
10	1.5∶1	DBU (1.0)	EtOH	120	5	71
11	2∶1	DBU (1.0)	EtOH	120	5	55
12	1.5∶1	DBU (1.0)	THF	120	5	58
13	1.5∶1	DBU (1.0)	CHCl₃	120	5	51
14	1.5∶1	DBU (1.0)	EtOAc	120	5	Trace
15	1.5∶1	DBU (1.0)	Toluene	120	5	30
16	1.5﹕1	DBU (1.0)	CH₃CN	120	5	42
17	1.5∶1	DBU (1.0)	Dry EtOH	120 (N₂)	5	77
18	1.5∶1	DBU (1.0)	Dry EtOH	100 (N₂)	5	70
19	1.5∶1	DBU (1.0)	Dry EtOH	130 (N₂)	5	75
20	1.5∶1	DBU (1.0)	Dry EtOH	120 (N₂)	4	81
21	1.5∶1	DBU (1.0)	Dry EtOH	120 (N₂)	6	72

基于2-硝基查尔酮与异氰基乙酸乙酯的串联环化反应合成α-咔啉酮类化合物

Synthesis of α-Carbolinone Compounds Based on Tandem Cyclization Reaction of 2-Nitrochalcone and Ethyl Isocyanoacetate

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