Citation: Hu Xiaoyu, Yu Haifeng, Wang Wenju, Jiang Siao, Liu Qi, He Jie. Synthesis of 3-Ethanoyl/Aroylacetylindoles in Water[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3183-3189. doi: 10.6023/cjoc201904002 shu

Synthesis of 3-Ethanoyl/Aroylacetylindoles in Water

College of Chemistry, Baicheng Normal University, Baicheng, Jilin 137000

Corresponding author: Yu Haifeng, yuhf68105@sina.com Wang Wenju, wangwj3309@126.com
Received Date: 3 April 2019
Revised Date: 18 June 2019
Available Online: 9 November 2019
Fund Project: Project supported by the Foundation of Science and Technology Research Projects of the 13th Five-Year Plan of Jilin Provincial Department of Education (No. 2016037)the Foundation of Science and Technology Research Projects of the 13th Five-Year Plan of Jilin Provincial Department of Education 2016037

Figures(2)

4-Dodecylbenzenesulfonic acid (DBSA) catalyzed hydrolysis reaction of β-ethylthio-β-indolyl-α, β-unsaturated ketones (1) in water to yield 3-ethanoyl/aroylacetylindoles (2) was studied. It showed that the hydrolysis of 1 in water smoothly occurred in the presence of 10 mol% DBSA in reflux water, and 2 was obtained in excellent yield.
- aqueous reaction,
- hydrolysis reaction,
- 3-acetoacetylindole,
- β-ethylthio-β-indolyl-α, β-unsaturated ketone
1. [1]
  Goldgur, Y.; Craigie, R.; Cohen, G. H.; Fujiwara, T.; Yoshinaga, T.; Fujishita, T.; Sugimoto, H.; Endo, T.; Murai, H.; Davies, D. R. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 13040. doi: 10.1073/pnas.96.23.13040
2. [2]
  Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379. doi: 10.1016/S0968-0896(02)00239-0
3. [3]
  Jain, S. V.; Sonawane, L. V.; Patil, R. R.; Bari, S. B. Med. Chem. Res. 2012, 21, 165. doi: 10.1007/s00044-010-9520-1
4. [4]
  Zhang, D. T.; Wang, G. T.; Tan, C. B.; Xu, W. R.; Pei, Y.; Huo, L. Y. Arch. Pharm. Res. 2011, 34, 343. doi: 10.1007/s12272-011-0301-2
5. [5]
  Diana, P.; Carbone, A.; Barraja, P.; Kelter, G.; Fiebig, H. H.; Cirrincione, G. Bioorg. Med. Chem. 2010, 18, 4524. doi: 10.1016/j.bmc.2010.04.061
6. [6]
  Carbone, A.; Spanò, V.; Parrino, B.; Ciancimino, C.; Attanasi, O. A.; Favi, G. Molecules 2013, 18, 2518. doi: 10.3390/molecules18032518
7. [7]
  Bergman, J. Acta Chem. Scand. 1968, 22, 1063. doi: 10.3891/acta.chem.scand.22-1063
8. [8]
  Pais, G. C. G.; Zhang, X. C.; Marchand, C.; Neamati, N.; Cowansage, K.; Svarovskaia E. S.; Pathak, V. K.; Tang, Y.; Nicklaus, M.; Pommier, Y.; Burke, T. R. J. Med. Chem. 2002, 45, 3184. doi: 10.1021/jm020037p
9. [9]
  Kostryukova, T. S.; Ivanovskaya, N. P.; Lyamin, A. I.; Romanov, D. V.; Osin, N. S.; Zatonsky, G. V.; Vasil'ev N. V. Russ. J. Gen. Chem. 2012, 82, 455. doi: 10.1134/S1070363212030152
10. [10]
  Yu, H. F.; Li, T. C.; Liao, P. Q.; Diao, Q. P.; Xin, G.; Hou, D. Y. Chin. J. Org. Chem. 2014, 34, 956 (in Chinese).
11. [11]
  Yu, H. F.; Liao, P. Q.; Diao, Q. P.; Li, T. C.; Xin, G.; Han, L. N.; Hou, D. Y. Chin. J. Org. Chem. 2014, 34, 1851 (in Chinese).
12. [12]
  Wang, W. J.; Yu, H. F. Synth. Commun. 2019, 49, 377. doi: 10.1080/00397911.2018.1555851
13. [13]
  Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209. doi: 10.1021/ar000145a
14. [14]
  Zhou, Z.; Duan, J. F.; Mu, X. J.; Xiao, S. Y. Chin. J. Org. Chem. 2018, 38, 585 (in Chinese).
15. [15]
  Xu, Z. H.; Chen, F. B.; Li, Y. Y.; Huang, Q. S.; Liao, C. W. Chin. J. Org. Chem. 2018, 38, 3101 (in Chinese).
16. [16]
  Wang, Z.; Yang, L.; Liu, H. L.; Bao, W. H.; Tan, Y. H.; Wang, M.; Tang, Z. L.; He, W. M. Chin. J. Org. Chem. 2018, 38, 2639 (in Chinese).
17. [17]
  Xie, L. Y.; Li, Y. J.; Qu, J.; Duan, Y.; Hu, J.; Liu, K. J.; Cao, Z.; He, W. M. Green Chem. 2017, 19, 5642. doi: 10.1039/C7GC02304A
18. [18]
  Xie, L. Y.; Peng, S.; Tan, J. X.; Sun, R. X.; Yu, X. Y.; Dai, N. N.; Tang, Z. L.; Xu, X. H.; He, W. M. ACS Sustainable Chem. Eng. 2018, 6, 16976. doi: 10.1021/acssuschemeng.8b04339
19. [19]
  Xie, L. Y.; Peng, S.; Liu, F.; Liu, Y. F.; Sun, M.; Tang, Z. L.; Jiang, S.; Cao, Z.; He, W. M. ACS Sustainable Chem. Eng. 2019, 77, 7193.
20. [20]
  Dong, D. W.; Ouyang, Y.; Yu, H. F.; Liu, Q.; Liu, J.; Wang, M.; Zhu, J. J. Org. Chem. 2005, 70, 4535. doi: 10.1021/jo050271y
21. [21]
  Yu, H. F.; Liao, P. Q. Tetrahedron Lett. 2016, 57, 2868. doi: 10.1016/j.tetlet.2016.05.062
22. [22]
  Qi, F.; Yu, H. F.; Wang, Y. N.; Lv, Y.; Li, Y. X.; Han, L.; Wang, R.; Feng, X. N. Synth. Commun. 2017, 47, 2220. doi: 10.1080/00397911.2017.1368084
23. [23]
  Pan, L.; Bi, X. H.; Liu, Q. Chem. Soc. Rev. 2013, 42, 1251. doi: 10.1039/C2CS35329F
24. [24]
  Yu, H. F.; Zhao, L. J.; Diao, Q. P.; Li, T. C.; Liao, P. Q.; Hou, D. Y.; Xin, G. Synlett 2017, 28, 1828. doi: 10.1055/s-0036-1588982
25. [25]
  Zhao H.; Diao, Q. P.; Yu, H. F.; Li, T. C.; Liao, P. Q.; Hou, D. Y. Chem. Res. Chin. Univ. 2017, 33, 746. doi: 10.1007/s40242-017-7082-1
26. [26]
  Yu, H. F.; Jin, W. W.; Sun, C. L.; Yu, Z. K. Angew. Chem., Int. Ed. 2010, 49, 5792. doi: 10.1002/anie.201002737
27. [27]
  Yu, H. F.; Yu, Z. K. Angew. Chem., Int. Ed. 2009, 48, 2929. doi: 10.1002/anie.200900278
28. [28]
  Yu, H. F.; Li, T. C.; Liao, P. Q. Synthesis 2012, 44, 3743. doi: 10.1055/s-0032-1317691
29. [29]
  Wang, Q.; Sun, Y. X.; Cui, S. Y.; Zhao, H.; Huang, W.; Xie, X. H. J. Mianyang Teachers' College 2017, 36, 30 (in Chinese).
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