Chinese Journal of Organic Chemistry >
Synthesis of 1,2,4-Triazoles via the Electrochemical Oxidative [3+2] Annulation
Received date: 2020-11-23
Revised date: 2021-01-24
Online published: 2021-02-22
Supported by
National Natural Science Foundation of China(21662045); Opening Foundation of the Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University(2018GDGP0103)
1,2,4-Triazoles, standing for a class of five-membered nitrogenous heterocyclic compounds, show anti-inflam- matory, anti-fungal and other biological activities. They also served as important intermediates in organic synthesis. Thus, the pursuit of general and efficient synthesis of 1,2,4-triazoles that controls the introduction of substituents in a highly regioselective fashion has been of continued interest to synthetic organic chemists. In this paper an electrochemical dehydrogenative [3+2] annulation used for the synthesis of 1,2,4-triazoles from cheap and readily available amines and hydrazones was developed. Their structures were confirmed by 1H NMR, 13C NMR and HRMS analyses. Advantageously, this method proceeds in a transition-metal-, acid-, base- and external oxidant-free fashion to provide a variety of functionalized 1,2,4-triazoles. The reaction constitutes a new transformation from hydrazones and amines to 1,2,4-triazoles, providing a unifying, simple and environmentally friendly approach to the currently available methods.
Zhiheng Zhao , Ming Li , Yaqin Zhou , Yonghui He , Lizhu Zhang , Ganpeng Li , Lijun Gu . Synthesis of 1,2,4-Triazoles via the Electrochemical Oxidative [3+2] Annulation[J]. Chinese Journal of Organic Chemistry, 2021 , 41(6) : 2476 -2484 . DOI: 10.6023/cjoc202011029
| [1] | Zhou,, P.-F.; Lin,, H.-M., Wang,, L.-W.; Mo,, Z.-Y.; Meng,, X.-J.; Tang,, H.-T.; Pan,, Y.-M. Green Chem. 2020, 22,6334. |
| [2] | Li, M. F.; Wang, R.; Hao, W. J.; Jiang, B. Chin. J. Org. Chem. 2020, 40,1540(in Chinese). |
| [2] | (李梦帆, 王榕, 郝文娟, 姜波, 有机化学, 2020, 40,1540.) |
| [3] | Xiong, P.; Xu, H. C. Acc. Chem. Res. 2019, 52,3339. |
| [4] | Sun, X.; Sun, C.; Feng, L.; Kang, C. Chin. J. Org. Chem. 2020, 40,2626(in Chinese). |
| [4] | (孙晓华, 孙传策, 冯立军, 康从民, 有机化学, 2020, 40,2626.) |
| [5] | Liu, Y.; Meng, J.; Li, C.; Lin, L.; Xu, Y. Chin. J. Org. Chem. 2020, 40,2742(in Chinese). |
| [5] | (刘颖杰, 孟建萍, 李晨, 林立青, 许颖, 有机化学, 2020, 40,2742.) |
| [6] | Moulin, A.; Bibian, M.; Blayo, A.-L.; El Habnouni, S.; Martinez, J.; Fehrentz, J.-A. Chem. Rev. 2010, 110,1809. |
| [7] | Kaku, Y.; Tsuruoka, A.; Kakinuma, H.; Tsukada, I.; Yanagisawa, M.; Naito, T. Chem. Pharm. Bull. 1998, 46,1125. |
| [8] | Koltin, Y.; Hitchcock, C. A. Curr. Opin. Chem. Biol. 1997, 1,176. |
| [9] | Haycock-Lewandowski, S. J.; Wilder, A.; Ahman, J. Org. Process Res. Dev. 2008, 12, 1094. |
| [10] | Turner, K. Org. Process Res. Dev. 2012, 16,727. |
| [11] | Guru, M. M.; Punniyamurthy, T. J. Org. Chem. 2012, 77,5063. |
| [12] | Zhang, L.; Tang, D.; Gao, J.; Wang, J.; Wu, P.; Meng, X. Synthesis 2016, 48,3924. |
| [13] | Gelmi, M. L.; Pocar, D.; Riva, R. Heterocycles 1992, 34,315. |
| [14] | Stocks, M. J.; Cheshire, D. R.; Reynolds, R. Org. Lett. 2004, 6,2969. |
| [15] | Bechara, W. S.; Khazhieva, I. S.; Rodriguez, E.; Charette, A. B. Org. Lett. 2015, 17,1184. |
| [16] | Klingsberg, E. J. Org. Chem. 1958, 23,1086. |
| [17] | Yang, N; Yuan, G. J. Org. Chem. 2018, 83, 11963. |
| [18] | Kuang, J.-Q.; Chen, B.; Ma, S.-M. Org. Chem. Front. 2014, 1,186. |
| [19] | Wang, L.-Y.; Tsai, H.-J.; Lin, H.-Y.; Kaneko, K.; Cheng, F.-Y.; Shih, H.-S.; Wong, F.-F.; Huang, J.-J. RSC Adv. 2014, 4,14215. |
| [20] | Zhang, C.; Liang, Z.; Jia, X.; Wang, M.; Zhang, G.; Hu, M.-L. Chem. Commun. 2020, 56,14215. |
| [21] | Li, X.; Ye, X.; Wei, C.; Shan, C.; Wojtas, L.; Wang, Q.; Shi, X. Org. Lett. 2020, 22,4151. |
| [22] | Liu, J.-Q.; Shen, X.; Wang, Y.; Wang, X.-S.; Bi, X. Org. Lett. 2018, 20,6930. |
| [23] | Chen, Z.; Li, H.; Dong, W.; Miao, M.; Ren, H. Org. Lett. 2016, 18,1334. |
| [24] | Jiao, K.-J.; Xing, Y.-K.; Yang, Q.-L.; Qiu, H.; Mei, T.-S. Acc. Chem. Res. 2020, 53, 300. |
| [25] | Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52,3309. |
| [26] | Luo, M.-J.; Li, Y.; Ouyang, X.-H.; Li, J.-H.; He, D.-L. Chem. Commun. 2020, 56,2707. |
| [27] | Tang, H.-T.; Jia, J.-S.; Pan, Y.-M. Org. Biomol. Chem. 2020, 18,5315. |
| [28] | Shi, S.-H.; Liang, Y.; Jiao, N. Chem. Rev. 2021, 485,121. |
| [29] | Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118,4485. |
| [30] | Qian, P.; Yan, Z.; Zhou, Z.; Hu, K.; Wang, J.; Li, Z.; Zha, Z.; Wang, Z. J. Org. Chem. 2019, 84,3148. |
| [31] | Zhou, Y.; Zhao, Z.; Zeng, L.; Li, M.; He, Y.; Gu, L. Chin. J. Org. Chem. 2021, 41,1072(in Chinese). |
| [31] | (周娅琴, 赵志恒, 曾亮, 李鸣, 何永辉, 谷利军, 有机化学, 2021, 41,1072.) |
| [32] | Zeng, L.; Li, J.; Gao, J.; Huang, X.; Wang, W.; Zheng, X.; Gu, L.; Li, G.; Zhang, S.; He, Y. Green Chem. 2020, 22,3416. |
| [33] | Asiri, A. M.; Fatani, N. A. Dyes Pigm. 2007, 72,217. |
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