Electrochemically Promoted Halogenation of Imidazoland-[1,2-a]pyridine with Dichloro(bromo)ethylene and Iodoform

doi:10.6023/cjoc202212014

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (6): 2104-2109.DOI: 10.6023/cjoc202212014 Previous Articles Next Articles

电化学促进咪唑并[1,2-a]吡啶与二氯(溴)乙烷及碘仿的卤化反应

张周^a, 郭钰^b, 羊静^b, 吴丹^b, 王佳昕^b, 洪欣玥^b, 蔡佩君^a^,^*(), 荣良策^b^,^*()

a 中国矿业大学化工学院江苏徐州 221116
b 江苏师范大学化学与材料科学学院江苏徐州 221116

收稿日期:2022-12-12 修回日期:2023-01-07 发布日期:2023-01-18
通讯作者: 蔡佩君, 荣良策
基金资助:
江苏省高校自然科学研究(18KJA150004); 大学生创新创业训练计划和江苏省高校品牌专业资助项目

Electrochemically Promoted Halogenation of Imidazoland-[1,2-a]pyridine with Dichloro(bromo)ethylene and Iodoform

Zhou Zhang^a, Yu Guo^b, Jing Yang^b, Dan Wu^b, Jiaxin Wang^b, Xinyue Hong^b, Peijun Cai^a,*(), Liangce Rong^b,*()

a Department of Chemical Engineering &Technology, China University of Mining and Technology, Xuzhou, Jiangsu 221004
b School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116

Received:2022-12-12 Revised:2023-01-07 Published:2023-01-18
Contact: * E-mail: lcrong@jsnu.edu.cn;caipj@163.com
Supported by:
Natural Science Foundation of the Jiangsu Higher Education Institutions(18KJA150004); Undergraduate Innovation and Entrepreneurship Training Program and the Brand Major of Universities in Jiangsu Province

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Abstract

An electrochemical halogenation of 2-arylimidazoland[1,2-a]pyridine with dichloro(bromo)ethylene and iodoform is reported. Studies show that dichloroethane, dibromoethane and iodoform are excellent halogen source reagents in this synthesis. The present protocol provides alternative route to obtain 3-halogenatedimidazo[1,2-a]pyridines derivatives.

Key words: electrochemistry, halogenation, imidazoland[1,2-a]pyridine, dichloro(bromo)ethylene, iodoform

Cite this article

Zhou Zhang, Yu Guo, Jing Yang, Dan Wu, Jiaxin Wang, Xinyue Hong, Peijun Cai, Liangce Rong. Electrochemically Promoted Halogenation of Imidazoland-[1,2-a]pyridine with Dichloro(bromo)ethylene and Iodoform[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2104-2109.

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Fig. & Tab. 4

References 19

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Entry	A/C	Electrolyte	Solvent	Current/mA	t/h	Yield^b/%
1	C(+)Pt(–)	ⁿBu₄NBF₄	DCE	10	3	73
2	Pt(+)Pt(–)	ⁿBu₄NBF₄	DCE	10	3	20
3	RVC(+) Pt(–)	ⁿBu₄NBF₄	DCE	10	3	25
4	C(+)Ni(–)	ⁿBu₄NBF₄	DCM	10	3	42
5	C(+)Pt(–)	ⁿBu₄NBF₄	DCM	10	3	47
6	C(+)Pt(–)	ⁿBu₄NBF₄	CHCl₃	10	3	62
7	C(+)Pt(–)	ⁿBu₄NBF₄	CCl₄	10	3	N.R.
8	C(+)Pt(–)	TBAB	DCE	10	3	80
9	C(+)Pt(–)	TBAC	DCE	10	3	68
10	C(+)Pt(–)	TEAC	DCE	10	3	68
11	C(+)Pt(–)	NH₄I	DCE	10	3	48
12	C(+)Pt(–)	TBAB	DCE	15	3	54
13	C(+)Pt(–)	TBAB	DCE	6	3	38
14	C(+)Pt(–)	TBAB	DCE	10	2.5	85
15	C(+)Pt(–)	TBAB	DCE	10	2.0	61
16	C(+)Pt(–)	TBAB	DCE	—	2.5	N.R.

Entry	A/C	Electrolyte	Solvent	Current/mA	t/h	Yield^b/%
1	C(+)Pt(–)	ⁿBu₄NBF₄	DCE	10	3	73
2	Pt(+)Pt(–)	ⁿBu₄NBF₄	DCE	10	3	20
3	RVC(+) Pt(–)	ⁿBu₄NBF₄	DCE	10	3	25
4	C(+)Ni(–)	ⁿBu₄NBF₄	DCM	10	3	42
5	C(+)Pt(–)	ⁿBu₄NBF₄	DCM	10	3	47
6	C(+)Pt(–)	ⁿBu₄NBF₄	CHCl₃	10	3	62
7	C(+)Pt(–)	ⁿBu₄NBF₄	CCl₄	10	3	N.R.
8	C(+)Pt(–)	TBAB	DCE	10	3	80
9	C(+)Pt(–)	TBAC	DCE	10	3	68
10	C(+)Pt(–)	TEAC	DCE	10	3	68
11	C(+)Pt(–)	NH₄I	DCE	10	3	48
12	C(+)Pt(–)	TBAB	DCE	15	3	54
13	C(+)Pt(–)	TBAB	DCE	6	3	38
14	C(+)Pt(–)	TBAB	DCE	10	2.5	85
15	C(+)Pt(–)	TBAB	DCE	10	2.0	61
16	C(+)Pt(–)	TBAB	DCE	—	2.5	N.R.

Product	R	X	Ar	Yield^b/%	m.p./℃
3aa	H	Cl	C₆H₅	85	119.5~121.4 (117~119)^[11]
3ab	H	Cl	4-ClC₆H₄	75	105.4~107.6 (103~105)^[11]
3ac	H	Cl	4-BrC₆H₄	74	126.7~129.4 (125.6~128.1)^[11]
3ad	H	Cl	3-ClC₆H₄	82	136.9~138.2 (134~136)^[9]
3ae	H	Cl	3-BrC₆H₄	84	124~126
3af	H	Cl	4-CF₃OC₆H₄	74	71.5~73.8
3ag	H	Cl	4-CH₃OC₆H₄	40	119.9~121.8 (123~125)^[6]
3ah	H	Cl	4-CH₃C₆H₄	56	122~124 (124~126)^[6]
3ai	6-CH₃	Cl	C₆H₅	75	138~139 (140.6~142.3)^[9]
3aj	6-Cl	Cl	C₆H₅	81	158~160 (158.5~161.3)^[9]
3ba	H	Br	C₆H₅	87	83.5~84.6 (80~82)^[11]
3bb	H	Br	4-ClC₆H₄	73	141.2~144.3 (136~138)^[11]
3bc	H	Br	4-BrC₆H₄	72	160.4~162.8 (159~161)^[4]
3bd	H	Br	3-ClC₆H₄	80	123.4~125.6 (118)^[17]
3be	H	Br	3-BrC₆H₄	81	127~129 (132~135)^[18]
3bf	H	Br	4-CH₃OC₆H₄	51	93.5~97.4 (92~94)^[11]
3bg	6-Br	Br	C₆H₅	87	152~154 (150~152)^[3a]
3bh	6-Cl	Br	C₆H₅	82	98~99 (102)^[17]
3ca	H	I	C₆H₅	76	156.0~157.8 (158.2~160.1)^[11]
3cb	H	I	4-ClC₆H₄	65	158.1~160.3 (159.0~162.3)^[11]
3cc	H	I	4-BrC₆H₄	68	136.4~138.9 (135~140)^[10]
3cd	H	I	3-ClC₆H₄	74	150~151 (152~154)^[19]
3ce	6-Br	I	C₆H₅	85	173~175 (178)^[3c]
3cf	6-Cl	I	4-BrC₆H₄	86	177~179 (175~178)^[10]

Product	R	X	Ar	Yield^b/%	m.p./℃
3aa	H	Cl	C₆H₅	85	119.5~121.4 (117~119)^[11]
3ab	H	Cl	4-ClC₆H₄	75	105.4~107.6 (103~105)^[11]
3ac	H	Cl	4-BrC₆H₄	74	126.7~129.4 (125.6~128.1)^[11]
3ad	H	Cl	3-ClC₆H₄	82	136.9~138.2 (134~136)^[9]
3ae	H	Cl	3-BrC₆H₄	84	124~126
3af	H	Cl	4-CF₃OC₆H₄	74	71.5~73.8
3ag	H	Cl	4-CH₃OC₆H₄	40	119.9~121.8 (123~125)^[6]
3ah	H	Cl	4-CH₃C₆H₄	56	122~124 (124~126)^[6]
3ai	6-CH₃	Cl	C₆H₅	75	138~139 (140.6~142.3)^[9]
3aj	6-Cl	Cl	C₆H₅	81	158~160 (158.5~161.3)^[9]
3ba	H	Br	C₆H₅	87	83.5~84.6 (80~82)^[11]
3bb	H	Br	4-ClC₆H₄	73	141.2~144.3 (136~138)^[11]
3bc	H	Br	4-BrC₆H₄	72	160.4~162.8 (159~161)^[4]
3bd	H	Br	3-ClC₆H₄	80	123.4~125.6 (118)^[17]
3be	H	Br	3-BrC₆H₄	81	127~129 (132~135)^[18]
3bf	H	Br	4-CH₃OC₆H₄	51	93.5~97.4 (92~94)^[11]
3bg	6-Br	Br	C₆H₅	87	152~154 (150~152)^[3a]
3bh	6-Cl	Br	C₆H₅	82	98~99 (102)^[17]
3ca	H	I	C₆H₅	76	156.0~157.8 (158.2~160.1)^[11]
3cb	H	I	4-ClC₆H₄	65	158.1~160.3 (159.0~162.3)^[11]
3cc	H	I	4-BrC₆H₄	68	136.4~138.9 (135~140)^[10]
3cd	H	I	3-ClC₆H₄	74	150~151 (152~154)^[19]
3ce	6-Br	I	C₆H₅	85	173~175 (178)^[3c]
3cf	6-Cl	I	4-BrC₆H₄	86	177~179 (175~178)^[10]

电化学促进咪唑并[1,2-a]吡啶与二氯(溴)乙烷及碘仿的卤化反应

Electrochemically Promoted Halogenation of Imidazoland-[1,2-a]pyridine with Dichloro(bromo)ethylene and Iodoform

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