Eco-friendly C-3 Selenation of Imidazo[1,2-a]pyridines in Ionic Liquid

doi:10.6023/cjoc201904057

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2802-2807.DOI: 10.6023/cjoc201904057 Previous Articles Next Articles

ARTICLE

咪唑并吡啶在离子液中环境友好型的C-3位硒化反应

王薪^*(), 穆石强, 孙婷, 孙凯^*()

安阳师范学院安阳 455000

收稿日期:2019-04-24 修回日期:2019-06-12 发布日期:2019-07-09
通讯作者: 王薪,孙凯 E-mail:wangx933@nenu.edu.cn;sunk468@nenu.edu.cn
基金资助:
国家自然科学基金(21801007);河南省教育厅创新团队资助项目(18IRTSTHN004);河南省教育厅创新团队资助项目(18HASTIT006)

Eco-friendly C-3 Selenation of Imidazo[1,2-a]pyridines in Ionic Liquid

Wang Xin^*(), Mu Shiqiang, Sun Ting, Sun Kai^*()

College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455000

Received:2019-04-24 Revised:2019-06-12 Published:2019-07-09
Contact: Wang Xin,Sun Kai E-mail:wangx933@nenu.edu.cn;sunk468@nenu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China(21801007);The Program for Innovative Research Team of Science and Technology in the University of Henan Province(18IRTSTHN004);The Program for Innovative Research Team of Science and Technology in the University of Henan Province(18HASTIT006)

An relative eco-friendly protocol for the direct C-3 selenation of imidazo[1,2-a]pyridines with vorious organoselenides has been developed, gaving the desired products in moderate to excellent yields. Preliminary experimental results are consistent with a C-3 electrophilic functionalization mechanism. The features with relative green reaction conditions, broad substrate scope, and easy scale-up operation would make this strategy promising and important for the preparation of nitrogen and selenium containing molecules.

Key words: selenation, imidazo[1,2-a]pyridines, C-3 functionalization, electrophilic mechanism

Cite this article

Wang Xin, Mu Shiqiang, Sun Ting, Sun Kai. Eco-friendly C-3 Selenation of Imidazo[1,2-a]pyridines in Ionic Liquid[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2802-2807.

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Fig. & Tab. 7

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Entry	Iodine source	Oxidant	Solvent	Yield^b/% of 3a/4
1	KI	TBHP	EtOAc	41/0^c
2	KI	TBHP	EtOH	23/0^c
3	KI	TBHP	H₂O	0/0^c
4	KI	TBHP	DMSO	55/0^c
5	KI	TBHP	Ionic liquid I	67/0^d
6	KI	TBHP	Ionic liquid II	43/0^e
7	I₂	TBHP	Ionic liquid I	51/Trace^f
8	I₂	No	Ionic liquid I	84/Trace^g
9	I₂	No	Ionic liquid I	33/23^h
10	I₂	No	Ionic liquid I	56/Traceⁱ

Entry	Iodine source	Oxidant	Solvent	Yield^b/% of 3a/4
1	KI	TBHP	EtOAc	41/0^c
2	KI	TBHP	EtOH	23/0^c
3	KI	TBHP	H₂O	0/0^c
4	KI	TBHP	DMSO	55/0^c
5	KI	TBHP	Ionic liquid I	67/0^d
6	KI	TBHP	Ionic liquid II	43/0^e
7	I₂	TBHP	Ionic liquid I	51/Trace^f
8	I₂	No	Ionic liquid I	84/Trace^g
9	I₂	No	Ionic liquid I	33/23^h
10	I₂	No	Ionic liquid I	56/Traceⁱ

咪唑并吡啶在离子液中环境友好型的C-3位硒化反应

Eco-friendly C-3 Selenation of Imidazo[1,2-a]pyridines in Ionic Liquid

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References 16

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