Chinese Journal of Organic Chemistry >
Tetrabutylammonium Iodide-Mediated One-Pot Construction of 1,3,4-Oxadiazole Derivatives with Alkyl Amide and Hydrazine
Received date: 2023-04-04
Revised date: 2023-06-02
Online published: 2023-07-06
Supported by
National Natural Science Foundation of China(21961038); Shanghai Cooperation Organization Science and Technology Partnership Program(2022E01049)
1,3,4-Oxadiazole derivatives are a class of important bioactive molecules, showing good antibacterial, anti-inflam- matory and anticancer activities. In the present study, an efficient one-pot synthetic methodology has been developed for the construction of 1,3,4-oxadiazoles by utilizing acylhydrazine and alkylamide as reactants in the absence of alkaline or metallic catalysts. The expected 1,3,4-oxadiazole derivatives can be obtained with a maximum 85% yield for 10 h. This method has the advantages of simple operation, mild conditions, few by-products and wide range of substrates. And it can achieve gram preparation, showing good practical value. The mechanism study showed that the tautomerism of amide electron cloud, and the activity of tetrabutylammonium iodide (TBAI) and hydrazide carbonyl group played an important role in the reaction.
Zhixia Jing , Jianxi Du , Ping Jiang , Keyume Ablajan . Tetrabutylammonium Iodide-Mediated One-Pot Construction of 1,3,4-Oxadiazole Derivatives with Alkyl Amide and Hydrazine[J]. Chinese Journal of Organic Chemistry, 2023 , 43(11) : 3930 -3938 . DOI: 10.6023/cjoc202304005
| [1] | (a) Fan, Y.; He, Y.; Liu, X.; Hu, T.; Ma, H.; Yang, X.; Luo, X.; Huang, G. J. Org. Chem. 2016, 81, 6820. |
| [1] | (b) Bozorov, K.; Nie, L. F.; Zhao, J.; Aisa, H. A. Eur. J. Med. Chem. 2017, 140, 465. |
| [1] | (c) Liu, S.; Zhao, Z.; Wang, Y. Chem.-Eur. J. 2019, 25, 2423. |
| [1] | (d) Bostrom, J.; Hogner, A.; Llinas, A.; Wellner, E.; Plowright, A. T. J. Med. Chem. 2012, 55, 1817. |
| [2] | (a) Aksenov, A. V.; Khamraev, V.; Aksenov, N. A.; Kirilov, N. K.; Domenyuk, D. A.; Zelensky, V. A.; Rubin, M. RSC Adv. 2019, 9, 6636. |
| [2] | (b) Abd-Ellah, H. S.; Abdel-Aziz, M.; Shoman, M. E.; Beshr, E. A.; Kaoud, T. S.; Ahmed, A. F. Bioorg. Chem. 2016, 69, 48. |
| [2] | (c) Boudreau, M. A.; Ding, D.; Meisel, J. E.; Janardhanan, J.; Spink, E.; Peng, Z.; Qian, Y.; Yamaguchi, T.; Testero, S. A.; O'Daniel, P. I.; Leemans, E.; Lastochkin, E.; Song, W.; Schroeder, V. A.; Wolter, W. R.; Suckow, M. A.; Mobashery, S.; Chang, M. ACS Med. Chem. Lett. 2020, 11, 322. |
| [2] | (d) Padejjar Vasantha, S.; Poojary, B.; Bistuvalli Chandrashekarappa, R. J. Chin. Chem. Soc. 2019, 66, 638. |
| [2] | (e) Wang, P. Y.; Zhou, L.; Zhou, J.; Wu, Z. B.; Xue, W.; Song, B. A.; Yang, S. Bioorg. Med. Chem. Lett. 2016, 26, 1214. |
| [2] | (f) Valente, S.; Trisciuoglio, D.; Luca, T. D.; Nebbioso, A.; Labella, D.; Lenoci, A.; Bigogno, C.; Dondio, G.; Miceli, M.; Brosch, G.; Bufalo, D. D.; Altucci, L.; Mai, A. J. Med. Chem. 2014, 57, 6259. |
| [3] | (a) Najare, M. S.; Patil, M. K.; Nadaf, A. A.; Mantur, S.; Garbhagudi, M.; Gaonkar, S.; Inamdar, S. R.; Khazi, I. A. M. J. Mol. Struct. 2020, 1199. |
| [3] | (b) Liu, Y.; Xing, K. Q.; Deng, J. Y.; Zhu, M. X.; Wang, X. Y.; Zhu, W. G. Chin. Chem. Lett. 2007, 18, 573. |
| [4] | (a) Weng, C.; Liu, Z.; Guo, H.; Tan, S. Macromol. Chem. Phys. 2017, 218, 170094. |
| [4] | (b) Chwarzer, K.; Tullmann, C. P.; Grassl, S.; Gorski, B.; Brocklehurst, C. E.; Knochel, P. Org. Lett. 2020, 22, 1899. |
| [4] | (c) Hou, R. B.; Su, J. Y.; Zhang, L. L.; Li, D. F.; Xia, Y. J. Chem. Res. 2019, 43, 3. |
| [5] | (a) Stabile, P.; Lamonica, A.; Ribecai, A.; Castoldi, D.; Guercio, G.; Curcuruto, O. Tetrahedron Lett. 2010, 51, 4801. |
| [5] | (b) Li, M. F.; Wang, R.; Hao, W. J.; Jiang, B. Chin. J. Org. Chem. 2020, 40, 1540. (in Chinese) |
| [5] | (李梦帆, 王榕, 郝文娟, 姜波, 有机化学, 2020, 40, 1540.) |
| [5] | (c) Zhang, X.; He, J.; Cao, S. Asian J. Org. Chem. 2019, 8, 279. |
| [5] | (d) Fugard, A. J.; Thompson, B. K.; Slawin, A. M.; Taylor, J. E.; Smith, A. D. Org. Lett. 2015, 17, 5824. |
| [5] | (e) Green, L.; Livingstone, K.; Bertrand, S.; Peace, S.; Jamieson, C. Chem.-Eur. J. 2020, 26, 14866. |
| [6] | (a) Gao, Q.; Liu, S.; Wu, X.; Zhang, J.; Wu, A. Org. Lett. 2015, 17, 2960. |
| [6] | (b) Shivi, B.; Monika, G. J. Chem. Pharm. Res. 2011, 3, 137. |
| [7] | Li, Q.; Tao, Y.; Xu, D.; Zhang, H.; Duan, L. J. Chin. Chem. Soc. 2014, 61, 665. |
| [8] | (a) Niu, P.; Kang, J.; Tian, X.; Song, L.; Liu, H.; Wu, J.; Yu, W.; Chang, J. J. Org. Chem. 2015, 80, 1018. |
| [8] | (b) Chauhan, J.; Ravva, M. K.; Sen, S. Org. Lett. 2019, 21, 6562. |
| [9] | Wang, Q.; Wang, X.; Liu, Q.; Xie, G.; Ding, S.; Wang, X.; Fan, H. Org. Chem. Front. 2020, 7, 3912. |
| [10] | Fugard, A. J.; Thompson, B. K.; Slawin, A. M.; Taylor, J. E.; Smith, A. D. Org. Lett. 2015, 17, 5824. |
| [11] | Lu, F.; Gong, F.; Li, L. Eur. J. Org. Chem. 2020, 3257. |
| [12] | (a) Li, A. F.; Ruan, Y. B.; Jiang, Q. Q.; He, W. B.; Jiang, Y. B. Chem.-Eur. J. 2010, 16, 5794. |
| [12] | (b) Pouliot, M. F.; Angers, L.; Hamel, J. D.; Paquin, J. F. Org. Biomol. Chem. 2012, 10, 988. |
| [12] | (c) Chauhan, J.; Ravva, M. K.; Sen, S. Org. Lett. 2019, 21, 6562. |
| [13] | Yu, W.; Huang, G.; Zhang, Y. T.; Liu, H. X.; Dong, L. H.; Yu, X. J.; Li, Y. J.; Chang, J. B. J. Org. Chem. 2013, 78, 10337. |
| [14] | Wang, L.; Wang, Y. Y; Chen, Q.; He, M. Y. Tetrahedron Lett. 2018, 59, 1489. |
| [15] | Wang, Q.; Wang, X.; Liu, Q.; Xie, G.; Ding, S.; Wang, X. X; Fan, H. Org. Chem. Front. 2020, 7, 3912. |
| [16] | Shu, W. M.; Zhang, X. Zhang, X. X.; Li, M.; Wang, A. J.; Wu, A. X. J. Org. Chem. 2019, 84, 14919. |
| [17] | Wang, S.; Wang, K.; Kong, X.; Zhang, S.; Jiang, G.; Ji, F. Adv. Synth. Catal. 2019, 361, 3986. |
| [18] | (a) Wang, Q.; Mgimpatsang, K. C.; Konstantinidou, M.; Shishkina, S. V.; Do?mling, A. Org. Lett. 2019, 21, 7320. |
| [18] | (b) Zhang, L.; Yu, Y.; Tang, Q.; Yuan, J.; Ran, D.; Tian, B.; Pan, T.; Gan, Z. Synth. Commun. 2019, 50, 423. |
| [19] | (a) Suresh, D.; Kanagaraj, K.; Pitchumani, K. Tetrahedron Lett. 2014, 55, 3678. |
| [19] | (b) Wang, Y.; Meng, Xu.; Yang, Y. T.; Chen, B. H. Chem. Commun. 2015, 51, 1907. |
| [20] | Majji, G.; Rout, S. K.; Guin, S.; Gogoi, A.; Patel, B. K. RSC Adv. 2014, 4, 5357. |
| [21] | Su, X. L.; Ye, L.; Chen, J. J.; Liu, X. D.; Jiang, S. P.; Jiang, F. L.; Liu, X. Y. Angew. Chem., Int. Ed. 2021, 60, 380. |
| [22] | Zou, L. H.; Reball, J.; Mottweiler, J.; Bolm, C. Chem. Commun. 2012, 48, 11307. |
| [23] | (a) Zhang, Q. W.; Wang, B.; Ma, H. F.; Ablajan, K. New J. Chem. 2019, 43, 17000. |
| [23] | (b) Jia, Y. F.; Ablajan, K. Adv. Synth. Catal. 2023, 365, 244. |
| [23] | (c) Liang, J.; Ma, H. F.; Ablajan, K. Chin. J. Org. Chem. 2019, 39, 3169. |
| [24] | (a) Siwach, A.; Verma, P. K. BMC Chem. 2020, 14, 70. |
| [24] | (b) Gao, P.; Wang, J.; Bai, Z.; Cheng, H.; Xiao, J.; Lai, M.; Yang, D.; Fan, M. Tetrahedron Lett. 2016, 57, 4616. |
| [24] | (c) Dong, D. Q.; Zhang, H.; Wang, Z. L. RSC Adv. 2017, 7, 3780. |
| [24] | (d) Li, L. X.; Dong, D. Q.; Hao, S. H.; Wang, Z. L. Tetrahedron Lett. 2018, 59, 1517. |
| [25] | Zahra, D. G.; Karim, A. D. J. Chin. Chem. Soc. 2020, 67, 1446. |
| [26] | Gnanasekaran, K. K.; Nammalwar, B.; Murie, M.; Bunce, R. A. Tetrahedron Lett. 2014, 55, 6776. |
| [27] | Polshettiwar, V.; Varma, R. S. Tetrahedron Lett. 2008, 49, 879. |
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