Na2S2O8 Mediated C—H Amination of Imidazo[1,2-α]pyridines with Heteroaromatic Amines under Metal-Free Conditions

doi:10.6023/cjoc202311026

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1667-1674.DOI: 10.6023/cjoc202311026 Previous Articles Next Articles

ARTICLES

Na₂S₂O₈介导的咪唑并[1,2-α]吡啶与杂芳胺在无金属条件下的C—H胺化反应

孙一平^a, 陈德茂^b, 何玲^c^,^*(), 王祖利^b^,^*()

a 中国科学院兰州化学物理研究所固体润滑国家重点实验室兰州 730000
b 青岛农业大学化学与药学院青岛 266109
c 重庆大学药学院创新药物研究中心天然产物合成与药物研究重庆重点实验室重庆 401331

收稿日期:2023-11-24 修回日期:2024-01-02 发布日期:2024-01-11
基金资助:
国家自然科学基金(21772107); 山东省高等学校青创人才引育计划(2021)

Na₂S₂O₈ Mediated C—H Amination of Imidazo[1,2-α]pyridines with Heteroaromatic Amines under Metal-Free Conditions

Yiping Sun^a, Demao Chen^b, Ling He^c(), Zuli Wang^b()

a State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
b College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109
c Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331

Received:2023-11-24 Revised:2024-01-02 Published:2024-01-11
Contact: *E-mail: wangzulichem@163.com, heling2015@cqu.edu.cn
Supported by:
National Natural Science Foundation of China(21772107); Youth Innovation Team Project for Talent Introduction and Cultivation in Universities of Shandong Province(2021)

1. .pdf(2667KB)

Abstract

Cite this article

Yiping Sun, Demao Chen, Ling He, Zuli Wang. Na₂S₂O₈ Mediated C—H Amination of Imidazo[1,2-α]pyridines with Heteroaromatic Amines under Metal-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1667-1674.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 19

[1]	(a) Cecile, E.-G.; Alain, G. Mini-Reviews Med. Chem. 2007, 7, 888. pmid: 22662878
	(b) Stasyuk, A. J.; Banasiewicz, M.; Cyranski, M. K.; Gryko, D. T. J. Org. Chem. 2012, 77, 5552. doi: 10.1021/jo300643w pmid: 22662878
	(c) Li, Y.; Shu, K.; Liu, P.; Sun, P. Org. Lett. 2020, 22, 6304. pmid: 22662878
	(d) Zhang, J.; She, M.; Liu, L.; Liu, M.; Wang, Z.; Liu, H.; Sun, W.; Liu, X.; Liu, P.; Zhang, S.; Li, J. Chin. Chem. Lett. 2021, 32, 3083. pmid: 22662878
[2]	(a) Shi, T.; Sun, K.; Chen, X. L.; Zhang, Z. X.; Huang, X. Q.; Peng, Y. Y.; Qu, L. B.; Yu, B. Adv. Synth. Catal. 2020, 362, 2143.
	(b) Zhang, J.; Xie, S.; Liu, P.; Sun, P. Adv. Synth. Catal. 2020, 362, 2173.
[3]	(a) Yu, Y.; Yuan, Y.; Liu, H.; He, M.; Yang, M.; Liu, P.; Yu, B.; Dong, X.; Lei, A. Chem. Commun. 2019, 55, 1809.
	(b) Mondal, S.; Samanta, S.; Jana, S.; Hajra, A. J. Org. Chem. 2017, 82, 4504.
[4]	Kibriya, G.; Samanta, S.; Jana, S.; Mondal, S.; Hajra, A. J. Org. Chem. 2017, 82, 13722. doi: 10.1021/acs.joc.7b02582 pmid: 29172531
[5]	Liu, P.; Gao, Y.; Gu, W.; Shen, Z.; Sun, P. J. Org. Chem. 2015, 80, 11559.
[6]	Gui, Q.-W.; Jiang, H.; Guo, D.; Zhang, Y.; Shen, Q.-P.; Tang, S.; You, J.; Huo, Y.; Wang, H. Synthesis 2020, 52, 2713.
[7]	(a) Yang, D.; Sun, P.; Wei, W.; Liu, F.; Zhang, H.; Wang, H. Chem.- Eur. J. 2018, 24, 4423.
	(b) Zhang, H.; Wei, Q.; Wei, S.; Qu, J.; Wang, B. Eur. J. Org. Chem. 2016, 2016, 3373.
[8]	Gao, Y.; Chen, S.; Lu, W.; Gu, W.; Liu, P.; Sun, P. Org. Biomol. Chem. 2017, 15, 8102.
[9]	Luan, N. N.; Liu, Z. W.; Han, S. J.; Shen, L. H.; Li, J. Y.; Zou, D. P.; Wu, Y. J.; Wu, Y. S. Tetrahedron Lett. 2020, 61.
[10]	(a) Zhao, J. F.; Duan, X. H.; Guo, L. N. Chin. J. Org. Chem. 2017, 37, 2498 (in Chinese).
	( 赵景峰, 段新华, 郭丽娜, 有机化学, 2017, 37, 2498.) doi: 10.6023/cjoc201705003
	(b) Mandal, S.; Bera, T.; Dubey, G.; Saha, J.; Laha, J. K. ACS Catal. 2018, 8, 5085.
	(c) Dong, D.-Q.; Yang, H.; Shi, J.-L.; Si, W.-J.; Wang, Z.-L.; Xu, X.-M. Org. Chem. Front. 2020, 7, 2538.
	(d) Dong, D.; Sun, Y.; Li, G.; Yang, H.; Wang, Z.; Xu, X. Chin. J. Org. Chem. 2020, 40, 4071.
	(e) Xie, L.-Y.; Peng, S.; Liu, F.; Chen, G.-R.; Xia, W.; Yu, X.; Li, W.-F.; Cao, Z.; He, W.-M. Org. Chem. Front. 2018, 5, 2604.
	(f) Ilangovan, A.; Polu, A.; Satish, G. Org. Chem. Front. 2015, 2, 1616.
	(g) Han, Q.-Q.; Li, G.-H.; Sun, Y.-Y.; Chen, D.-M.; Wang, Z.-L.; Yu, X.-Y.; Xu, X.-M. Tetrahedron Lett. 2020, 61, 151704.
[11]	(a) Sun, K.; Si, Y. F.; Chen, X. L.; Lv, Q. Y.; Peng, Y. Y.; Qu, L. B.; Yu, B. Asian J. Org. Chem. 2019, 8, 2042.
	(b) Sun, K.; Li, S. J.; Chen, X. L.; Liu, Y.; Huang, X. Q.; Wei, D. H.; Qu, L. B.; Zhao, Y. F.; Yu, B. Chem. Commun. 2019, 55, 2861.
[12]	(a) Shi, Z.; Glorius, F. Chem. Sci. 2013, 4, 829.
	(b) More, N. Y.; Jeganmohan, M. Org. Lett. 2014, 16, 804.
[13]	(a) Wang, S.; Guo, L. N.; Wang, H.; Duan, X. H. Org. Lett. 2015, 17, 4798.
	(b) Sun, K.; Wang, X.; Lv, Y.; Li, G.; Jiao, H.; Dai, C.; Li, Y.; Zhang, C.; Liu, L. Chem. Commun. 2016, 52, 8471.
[14]	(a) Song, H.-Y.; Liu, M.-Y.; Huang, J.; Wang, D.; Jiang, J.; Chen, J.-Y.; Yang, T.-B.; He, W.-M. J. Org. Chem. 2023, 88, 2288.
	(b) Lu, Y.-H.; Zhang, Z.-T.; Wu, H.-Y.; Zhou, M.-H.; Song, H.-Y.; Ji, H.-T.; Jiang, J.; Chen, J.-Y.; He, W.-M. Chin. Chem. Lett. 2023, 34, 108036.
	(c) Ma, C.-H.; Zhao, L.; He, X.; Jiang, Y.-Q.; Yu, B. Org. Chem. Front. 2022, 9, 1445.
	(d) Cui, W.; Li, Y.; Li, X.; Li, J.; Song, X.; Lv, J.; Jiang, Y.-Y.; Yang, D. Chin. Chem. Lett. 2023, 34, 107477.
	(e) Yu, Q.; Liu, Y. Y.; Wan, J. P. Org. Chem. Front. 2020, 7, 2770.
[15]	(a) Han, Q.-Q.; Chen, D.-M.; Wang, Z.-L.; Sun, Y.-Y.; Yang, S.-H.; Song, J.-C.; Dong, D.-Q. Chin. Chem. Lett. 2021, 32, 2559.
	(b) Dong, D.-Q.; Song, J.-C.; Yang, S.-H.; Qin, Q.-X.; Wang, Z.-L.; Zhang, E.-X.; Sun, Y.-Y.; Han, Q.-Q.; Yue, S. Chin. Chem. Lett. 2022, 33, 1199.
	(c) Yang, S.-H.; Song, J.-C.; Yang, H.; Zhou, M.-Y.; Wei, Z.-H.; Gao, J.-H.; Dong, D.-Q.; Wang, Z.-L. Chin. Chem. Lett. 2023, 108131.
[16]	(a) Li, G.-H.; Han, Q.-Q.; Sun, Y.-Y.; Chen, D.-M.; Wang, Z.-L.; Xu, X.-M.; Yu, X.-Y. Chin. Chem. Lett. 2020, 31, 3255.
	(b) Sun, Y.; Song, J.; Qin, Q.; Zhang, E.; Han, Q.; Yang, S.; Wang, Z.; Yue, S.; Dong, D. Chin. J. Org. Chem. 2021, 41, 4651 (in Chinese).
	( 孙媛媛, 宋敬城, 秦启学, 张恩选, 韩晴晴, 杨少慧, 王祖利, 岳姗, 董道, 有机化学, 2021, 41, 4651.) doi: 10.6023/cjoc202106006
	(c) Han, Q. Q.; Sun, Y. Y.; Yang, S. H.; Song, J. C.; Wang, Z. L. Chin. Chem. Lett. 2021, 32, 3632.
	(d) Yang, W.-C.; Chen, C.-Y.; Li, J.-F.; Wang, Z.-L. Chin. J. Catal. 2021, 42, 1865.
	(e) Yang, S.-H.; Song, J.-C.; Dong, D.-Q.; Yang, H.; Zhou, M.-Y.; Zhang, H.-S.; Wang, Z.-L. Chin. J. Org. Chem. 2022, 42, 4099 (in Chinese).
	( 杨少慧, 宋敬城, 董道青, 杨昊, 周梦宇, 张会淑, 王祖利, 有机化学, 2022, 42, 4099.) doi: 10.6023/cjoc202207019
[17]	(a) Wang, Y. N.; Li, Q.; Fang, Y. L.; Gao, L. H.; Song, S. Z.; Dong, Y.; Wei, W. T. Asian J. Org. Chem. 2019, 8, 832.
	(b) Wu, Y.; Chen, J.-Y.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W.-M. Green Chem. 2021, 23, 3950.
[18]	Li, H.; Chen, P.; Wu, Z.; Lu, Y.; Peng, J.; Chen, J.; He, W. Chin. J. Org. Chem. 2022, 42, 3398 (in Chinese).
	( 李红霞, 陈棚, 伍智林, 陆雨函, 彭俊梅, 陈锦杨, 何卫民, 有机化学, 2022, 42, 3398.) doi: 10.6023/cjoc202207009
	(b) Mu, S.; Li, H.; Wu, Z.; Peng, J.; Chen, J.; He, W. Chin. J. Org. Chem. 2022, 42, 4292 (in Chinese).
	( 穆思宇, 李红霞, 伍智林, 彭俊梅, 陈锦杨, 何卫民, 有机化学, 2022, 42, 4292.) doi: 10.6023/cjoc202211002
	(c) Wang, K.; Huang, J.; Liu, W.; Wu, Z.; Yu, X.; Jiang, J.; He, W. Chin. J. Org. Chem. 2022, 42, 2527 (in Chinese).
	( 王苛莉, 黄静, 刘伟, 伍智林, 于贤勇, 蒋俊, 何卫民, 有机化学, 2022, 42, 2527.) doi: 10.6023/cjoc202203055
	(d) Lu, Y.-H.; Wu, C.; Hou, J.-C.; Wu, Z.-L.; Zhou, M.-H.; Huang, X.-J.; He, W.-M. ACS Catal. 2023, 13, 13071.
	(e) Ji, H.-T.; Wang, K.-L.; Ouyang, W.-T.; Luo, Q.-X.; Li, H.-X.; He, W.-M. Green Chem. 2023, 25, 7983.
	(f) Song, H.-Y.; Xiao, F.; Jiang, J.; Wu, C.; Ji, H.-T.; Lu, Y.-H.; Wang, K.-L.; He, W.-M. Chin. Chem. Lett. 2023, 34, 108509.
[19]	(a) Xu, Z.; Wan, J.; Liu, Y. Chin. J. Org. Chem. 2023, 43, 2425 (in Chinese).
	( 徐忠荣, 万结平, 刘云云, 有机化学, 2023, 43, 2425.)
	(b) Shi, L.; Li, T.; Mei, G.-J. Green Synth. Catal. 2022, 3, 227.
	(c) Ashitha, K. T.; Krishna, M. S, A.; D, B.; B. Somappa, S. Org. Chem. Front. 2022, 9, 5306.
	(d) Chen, D.; Jiang, J.; Wan, J.-P. Chin. J. Chem. 2022, 40, 2582.
	(e) Chen, X.; Ouyang, W.-T.; Li, X.; He, W.-M. Chin. J. Org. Chem. 2023, 43, 4213 (in Chinese).
	( 陈祥, 欧阳文韬, 李潇, 何卫民, 有机化学, 2023, 43, 4213.) doi: 10.6023/cjoc202307026
	(f) Song, H.-Y.; Jiang, J.; Wu, C.; Hou, J.-C.; Lu, Y.-H.; Wang, K.-L.; Yang, T.-B.; He, W.-M. Green Chem. 2023, 25, 3292.

Entry	Oxidant	Solvent	Yield^b/%
1	Na₂S₂O₈	DMF/H₂O	42
2	Na₂S₂O₈	MeCN/H₂O	76
3	Na₂S₂O₈	CHCl₃/H₂O	65
4	Na₂S₂O₈	DCE/H₂O	61
5	Na₂S₂O₈	Acetone/H₂O	49
6	Na₂S₂O₈	o-DCB/H₂O	59
7	Na₂S₂O₈	DCM/H₂O	91
8	K₂S₂O₈	DCM/H₂O	83
9	(NH₄)₂S₂O₈	DCM/H₂O	78
10	PIDA	DCM/H₂O	N.R.
11	PIFA	DCM/H₂O	N.R.
12	TBHP	DCM/H₂O	Trace
13	DTBP	DCM/H₂O	N.R.
14	DCP	DCM/H₂O	N.R.
15	TBPB	DCM/H₂O	N.R.
16	BPO	DCM/H₂O	42
18^c	Na₂S₂O₈	DCM/H₂O	78
19^d	Na₂S₂O₈	DCM/H₂O	85

Entry	Oxidant	Solvent	Yield^b/%
1	Na₂S₂O₈	DMF/H₂O	42
2	Na₂S₂O₈	MeCN/H₂O	76
3	Na₂S₂O₈	CHCl₃/H₂O	65
4	Na₂S₂O₈	DCE/H₂O	61
5	Na₂S₂O₈	Acetone/H₂O	49
6	Na₂S₂O₈	o-DCB/H₂O	59
7	Na₂S₂O₈	DCM/H₂O	91
8	K₂S₂O₈	DCM/H₂O	83
9	(NH₄)₂S₂O₈	DCM/H₂O	78
10	PIDA	DCM/H₂O	N.R.
11	PIFA	DCM/H₂O	N.R.
12	TBHP	DCM/H₂O	Trace
13	DTBP	DCM/H₂O	N.R.
14	DCP	DCM/H₂O	N.R.
15	TBPB	DCM/H₂O	N.R.
16	BPO	DCM/H₂O	42
18^c	Na₂S₂O₈	DCM/H₂O	78
19^d	Na₂S₂O₈	DCM/H₂O	85

Na₂S₂O₈介导的咪唑并[1,2-α]吡啶与杂芳胺在无金属条件下的C—H胺化反应

Na₂S₂O₈ Mediated C—H Amination of Imidazo[1,2-α]pyridines with Heteroaromatic Amines under Metal-Free Conditions

RichHTML

PDF

Supporting Info.