Chinese Journal of Organic Chemistry >
N-Iodosuccinimide-Promoted Regioselective Arylsulfenylation of Imidazo[1,2-a]pyridines with Disulfides
Received date: 2016-09-29
Revised date: 2016-11-07
Online published: 2016-11-17
Supported by
Project supported by the National Natural Science Foundation of China (No. 21502055), the Fundamental Research Funds for the Central Universities (No. 2015ZM150) and the China Postdoctoral Science Foundation (Nos. 2015M572303, 2016T90779).
An efficient and practical N-iodosuccinimide-promoted regioselective arylsulfenylation of imidazo[1,2-a]pyridines with disulfides has been developed to afford functionalized 3-sulfenylimidazo[1,2-a]pyridines heterocycles in moderate to good yields. Their structures were confirmed by IR, 1H NMR, 13C NMR and HRMS. Furthermore, this method has the advantages of mild reaction conditions, broad substrates scope and environmentally benign. Notably, the current methodology could also be conveniently applied to the synthesis of thioarylated naturally occurring biologically active frameworks.
An Yanni , Li Jianxiao , Li Meng , Li Chunsheng , Yang Shaorong . N-Iodosuccinimide-Promoted Regioselective Arylsulfenylation of Imidazo[1,2-a]pyridines with Disulfides[J]. Chinese Journal of Organic Chemistry, 2017 , 37(3) : 720 -725 . DOI: 10.6023/cjoc201609033
[1] (a) Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588.
(b) Ouyang, K.; Hao, W.; Zhang, W.-X.; Xi, Z. Chem. Rev. 2015, 115, 12045.
[2] (a) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205.
(b) Liu, H.; Jiang, X. Chem.-Asian J. 2013, 8, 2546.
[3] (a) Sahoo, S. K.; Banerjee, A.; Chakraborty, S.; Patel, B. K. ACS Catal. 2012, 2, 544.
(b) Wu, Z.; Song, H.; Cui, X.; Pi, C.; Du, W.; Wu, Y. Org. Lett. 2013, 15, 1270.
(c) Mao, J.; Jia, T.; Frensch, G.; Walsh, P. J. Org. Lett. 2014, 16, 5304.
[4] (a) Ham, J.; Yang, I.; Kang, H. J. Org. Chem. 2004, 69, 3236.
(b) Stoll, A. H.; Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 606.
(c) Yonova, I. M.; Osborne, C. A.; Morrissette, N. S.; Jarvo, E. R. J. Org. Chem. 2014, 79, 1947.
[5] (a) Dai, C.; Xu, Z.; Huang, F.; Yu, Z.; Gao, Y.-F. J. Org. Chem. 2012, 77, 4414.
(b) Yang, F. L.; Tian, S. K. Angew. Chem., Int. Ed. 2013, 52, 4929.
(c) Xiao, F.; Xie, H.; Liu, S.; Deng, G. J. Adv. Synth. Catal. 2014, 356, 364.
[6] (a) Hand, E. S.; Paudler, W. W. J. Org. Chem. 1978, 43, 2900.
(b) Gudmundsson, K. S.; Johns, B. A. Bioorg. Med. Chem. Lett. 2007, 17, 2735.
(c) Gao, Y.; Yin, M. Z.; Wu, W. Q.; Huang, H. W.; Jiang, H. F. Adv. Synth. Catal. 2013, 355, 2263.
[7] (a) Gao, Z.; Zhu, X.; Zhang, R. RSC Adv. 2014, 4, 19891.
(b) Bagdi, A. K.; Mitra, S.; Ghosh, M.; Hajra, A. Org. Biomol. Chem. 2015, 13, 3314.
[8] Huang, X.; Wang, S.; Li, B.; Wang, X.; Ge, Z.; Li, R. RSC Adv. 2015, 5, 22654.
[9] Cao, H.; Chen, L.; Liu, J.; Cai, H.; Deng, H.; Chen, G.; Yan, C.; Chen, Y. RSC Adv. 2015, 5, 22356.
[10] Rafique, J.; Saba, S.; Rosario, A. R.; Braga, A. L. Chem.-Eur. J. 2016, 22, 11854.
[11] (a) Li, X.; Xu, Y.; Wu, W.; Jiang, C.; Qi, C.; Jiang, H. Chem. Eur. J. 2014, 20, 7911.
(b) Xu, Y.; Tang, X.; Hu, W.; Wu, W.; Jiang, H. Green Chem. 2014, 16, 3720.
(c) Gao, Y.; Gao, Y.; Tang, X.; Peng, J.; Hu, M.; Wu, W.; Jiang, H. Org. Lett. 2016, 18, 1158.
[12] (a) Li, J.; Yang, S.; Jiang, H.; Wu, W.; Zhao, J. J. Org. Chem. 2013, 78, 12477.
(b) Li, J.; Yang, S.; Huang, L.; Chen, H.; Jiang, H. RSC Adv. 2013, 3, 11529.
(c) Li, J.; Yang, S.; Wu, W.; Jiang, H. Chem. Commun. 2014, 50, 1381.
(d) Li, J.; Li, C.; Yang, S.; Luo, W. Chin. J. Org. Chem. 2015, 35, 898 (in Chinese).(李建晓, 李春生, 杨少容, 罗维, 有机化学, 2015, 35, 898.)
(e) Li, J.; Zhu, Z.; Yang, S.; Zhang, Z.; Wu, W.; Jiang, H. J. Org. Chem. 2015, 80, 3870.
(f) Li, J.; Zhang, Z.; Li, C.; Luo, W.; Yang, S. Chin. J. Org. Chem. 2015, 35, 2199 (in Chinese). (李建晓, 张振明, 李春生, 罗维, 杨少容, 有机化学, 2015, 35, 2199.)
(g) An, Y.; Li, J.; Zhang, Z.; Li, C.; Yang, S. Chin. J. Org. Chem. 2016, 36, 2136 (in Chinese). (安艳妮, 李建晓, 张振明, 李春生, 杨少容, 有机化学, 2015, 36, 2136.)
[13] (a) Li, J.; Li, C.; Yang, S.; An, Y.; Wu, W.; Jiang, H. J. Org. Chem. 2016, 81, 2875.
(b) Li, J.; Li, C.; Yang, S.; An, Y.; Wu, W.; Jiang, H. J. Org. Chem. 2016, 81, 7771.
[14] Huang, D.; Chen, J.; Dan, W.; Ding, J.; Liu, M.; Wu, H. Adv. Synth. Catal. 2012, 354, 2123.
[15] Park, S.; Kazlauskas, R. J. J. Org. Chem. 2001, 66, 8395.
[16] Branco, L. C.; Rosa, J. N.; Ramos, J. J. M.; Afonso, C. A. M. Chem. Eur. J. 2002, 8, 3671.
[17] Miao, C. X.; He, L. N.; Wang, J. Q.; Wang, J. L. Adv. Synth. Catal. 2009, 351, 2209.
[18] Zheng, Z.; Qi, D.; Shi, L. Catal. Commun. 2015, 66, 83.
[19] Hiebel, M.-A.; Berteina-Raboin, S. Green Chem. 2015, 17, 937.
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