I2-Catalyzed Cyclization of β-Ketonitrile with 1H-Pyrazol-5-amine

doi:10.6023/cjoc202206017

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 195-201.DOI: 10.6023/cjoc202206017 Previous Articles Next Articles

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I₂催化β-酮腈与1H-吡唑-5-胺的环化反应

桑田, 贾帆, 何静, 李春天, 刘岩^*(), 刘平^*()

石河子大学化学化工学院化工绿色过程兵团重点实验室新疆石河子 832003

收稿日期:2022-06-12 修回日期:2022-08-16 发布日期:2022-09-15
通讯作者: 刘岩, 刘平
基金资助:
国家自然科学基金(21563025); 国家自然科学基金(22162022)

I₂-Catalyzed Cyclization of β-Ketonitrile with 1H-Pyrazol-5-amine

Tian Sang, Fan Jia, Jing He, Chuntian Li, Yan Liu(), Ping Liu()

Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003

Received:2022-06-12 Revised:2022-08-16 Published:2022-09-15
Contact: Yan Liu, Ping Liu
Supported by:
National Natural Science Foundation of China(21563025); National Natural Science Foundation of China(22162022)

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Abstract

An I₂-catalyzed cyclization reaction of 1H-pyrazol-5-amine and β-ketonitrile for the synthesis of pyrazolo[1,5- a]pyrimidines was developed. This method provides an efficient way to obtain structurally diverse pyrazolo[1,5-a]pyrimidine derivatives in good to excellent yields. The method has the advantages of simple operation, mild reaction conditions and a wide range of substrates. It can also be scaled up.

Key words: I₂-catalyzed, cyclization reaction, pyrazolo[1,5-a]pyrimidines

Cite this article

Tian Sang, Fan Jia, Jing He, Chuntian Li, Yan Liu, Ping Liu. I₂-Catalyzed Cyclization of β-Ketonitrile with 1H-Pyrazol-5-amine[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 195-201.

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Fig. & Tab. 7

References 15

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I₂催化β-酮腈与1H-吡唑-5-胺的环化反应

I₂-Catalyzed Cyclization of β-Ketonitrile with 1H-Pyrazol-5-amine

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Fig. & Tab. 7

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Entry	Catalyst (mol%)	Solvent/mL	T/℃	t/h	Yield^b/%
1	I₂(20)	EtOH	80	12	87
2^c	I₂(20)	EtOH	80	12	Trace
3	I₂(20)	DMSO	80	12	94
4^d	I₂(20)	EtOH	80	12	75
5	I₂(20)	DMF	80	12	56
6	I₂(20)	CH₃CN	80	12	28
7	TBAI (40)	EtOH	80	12	11
8	NIS (40)	EtOH	80	12	35
9	NBS (40)	EtOH	80	12	42
10	NCS (40)	EtOH	80	12	37
11	FeCl₃ (40)	DMSO	80	12	54
12	AlCl₃ (40)	DMSO	80	12	79
13	I₂ (10)	DMSO	80	12	64
14	I₂ (40)	DMSO	80	12	57
15	I₂(20)	DMSO	100	12	63
16	I₂(20)	DMSO	60	12	39
17	I₂(20)	DMSO	80	8	48

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I2催化β-酮腈与1H-吡唑-5-胺的环化反应