N-碘代丁二酰亚胺促进的咪唑并[1,2-a]吡啶衍生物的芳烃硫基化反应
收稿日期: 2016-09-29
修回日期: 2016-11-07
网络出版日期: 2016-11-17
基金资助
国家自然科学基金（No.21502055）、中央高校基本科研业务费（No.2015ZM150）和中国博士后科学基金（Nos.2015M572303，2016T90779）资助项目.
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).
以离子液体[Bmim]BF4为溶剂，实现了N-碘代丁二酰亚胺促进的咪唑并[1，2-a]吡啶衍生物与二芳基二硫醚发生的氧化芳烃硫基化反应，以中等至优良产率（73%~86%）合成系列烃硫基取代的含氮环化合物.其结构均经IR，1H NMR，13C NMR及HRMS确证.该反应具有反应条件温和、底物适用范围广、环境友好等优点，可为含有烃硫基取代的天然产物及复杂药物分子的合成提供潜在的合成途径.
关键词： N-碘代丁二酰亚胺; 离子液体; 咪唑并[1,2-a]吡啶; 二芳基二硫醚; 芳烃硫基化反应
安艳妮 , 李建晓 , 李蒙 , 李春生 , 杨少容 . N-碘代丁二酰亚胺促进的咪唑并[1,2-a]吡啶衍生物的芳烃硫基化反应[J]. 有机化学, 2017 , 37(3) : 720 -725 . DOI: 10.6023/cjoc201609033
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.
[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.
/
| 〈 |
|
〉 |
