Citation: Yunhao Zhang, Yinuo Wang, Siran Wang, Dazhen Xu. Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes[J]. University Chemistry, ;2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083 shu

Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes

Department of Chemistry, Nankai University, Tianjin 300071, China

Received Date: 30 January 2024
Revised Date: 25 April 2024

Nitrogen-containing aromatic compounds are ubiquitous in nature. They often exhibit a wide range of biological activities. Therefore, chemists have been studying on the preparation of them for a long time as well as developing various methods for their derivatization. Recently, the direct oxidation of nonaromatic cyclicsubstrates to prepare selectively substituted aromatics has been one of research focuses. In which, the functionalized aromatics could be obtained via C—C, C—N, C—S and C—Se bonds formation without the directing groups in one step. This paper reviews the recent progress in the construction of functional quinoline and indole by this method, and proposes future development prospects in this field.
- Indole,
- Quinoline,
- Dehydrogenation,
- Aromatization
1. [1]
  Stork, G.; Niu, D.; Fujimoto, A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239.
2. [2]
  Kaufman, T. S.; Rúveda, E. A. Angew. Chem. Int. Ed. 2005, 44, 854.
3. [3]
  Gao, J.; Tian, Z.; Yang, X. BioScience Trends. 2020, 14, 72.
4. [4]
  Comai, S.; Bertazzo, A.; Brughera, M.; Crotti, S. Adv. Clin. Chem. 2020, 95, 165.
5. [5]
  Mohammad-Zadeh, L. F.; Moses, L.; Gwaltney-Brant, S. M. J. vet. Pharmacol. Therap. 2008, 31, 187.
6. [6]
  Cho, C. S.; Lim, H. K.; Shim, S. C.; Kim, T. J.; Choi, H.-J. Chem. Commun. 1998, 995.
7. [7]
  Zhang, X.; Xu, X. Chem. Asian J. 2014, 9, 3089.
8. [8]
  Tan, Z.; Jiang, H.; Zhang, M. Org. Lett. 2016, 18, 3174.
9. [9]
  Tan, Z.; Jiang, H.; Zhang, M. Chem. Commun. 2016, 52, 9359.
10. [10]
  Jiang, X.; Tang, W.; Xue, D.; Xiao, J.; Wang, C. ACS Catal. 2017, 7, 1831.
11. [11]
  Borghs, J. C.; Zubar, V.; Azofra, L. M.; Sklyaruk, J.; Rueping, M. Org. Lett. 2020, 22, 4222.
12. [12]
  Jia, Z.; Yang, Q.; Zhang, L.; Luo, S. ACS Catal. 2019, 9, 3589.
13. [13]
  Chen, X.; Li, Y.; Chen, L.; Zhu, Z.; Li, B.; Huang, Y.; Zhang, M. J. Org. Chem. 2019, 84, 3559.
14. [14]
  Deraedt, C.; Ye, R.; Ralston, W. T.; Toste, F. D.; Somorjai, G. A. J. Am. Chem. Soc. 2017, 139, 18084.
15. [15]
  Reddy, K. H. V.; Satish, G.; Ramesh, K.; Karnakar, K.; Nageswar, Y. V. D. Tetrahedron Lett. 2012, 53, 3061.
16. [16]
  Mao, H.; Xu, R.; Wan, J.; Jiang, Z.; Sun, C.; Pan, Y. Chem. Eur. J. 2010, 16, 13352.
17. [17]
  Deb, I.; Das, D.; Seidel, D. Org. Lett. 2011, 13, 812.
18. [18]
  Wang, Z.; Zeng, H.; Li, C.-J. Org. Lett. 2019, 21, 2302.
19. [19]
  Aydin, O.; Kilic, H.; Bayindir, S.; Erdogan, E.; Saracoglu, N. J. Heterocyclic Chem. 2015, 52, 1540.
20. [20]
  Bayindir, S.; Erdogan, E.; Kilic, H.; Aydin, O.; Saracoglu, N. J. Heterocyclic Chem. 2015, 52, 1589.
21. [21]
  Chen, X.; Yang, Z.; Chen, X.; Liang, W.; Zhu, Z.; Xie, F.; Li, Y. J. Org. Chem. 2020, 85, 508.
22. [22]
  Qiu, Z.; Li, J.-S.; Li, C.-J. Chem. Sci. 2017, 8, 6954.
23. [23]
  Liang, Y.; Jiang, H.; Tan, Z.; Zhang, M. Chem. Commun. 2018, 54, 10096.
24. [24]
  Zhao, H.; Chen, X.; Jiang, H.; Zhang, M. Org. Chem. Front. 2018, 5, 539.
25. [25]
  Muralirajan, K.; Kancherla, R.; Rueping, M. Angew. Chem. Int. Ed. 2018, 57, 14787.
26. [26]
  Liu, C.; Peng, X.; Hu, D.; Shi, F.; Huang, P.; Luo, J.; Liu, Q.; Liu, L. New J. Chem. 2020, 44, 17245.
27. [27]
  Jiang, X.; Zhao, Z.; Shen, Z.; Chen, K.; Fang, L.; Yu, C. Eur. J. Org. Chem. 2020, 3889.
28. [28]
  Wang, H.; Li, Y.; Lu, Q.; Yu, M.; Bai, X.; Wang, S.; Cong, H.; Zhang, H.; Lei, A. ACS Catal. 2019, 9, 1888.
29. [29]
  Tan, Z.; Liang, Y.; Yang, J.; Cao, L.; Jiang, H.; Zhang, M. Org. Lett. 2018, 20, 6554.
30. [30]
  Liu, H.-L.; Zhang, R.-J.; Han, D.-Y.; Feng, Y.; Luo, T.-H.; Xu, D.-Z. J. Org. Chem. 2023, 88, 10058.
31. [31]
  Ou, Y.; Yang, T.; Tang, N.; Yin, S.-F.; Kambe, N.; Qiu, R. Org. Lett. 2021, 23, 6417.
32. [32]
  Ramakumar, K.; Tunge, J. A. Chem. Commun. 2014, 50, 13056.
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