Citation: Du Xingpeng, Zhang Xi, Hou Fei, Liu Xiaojun, Wang Xicun, Quan Zhengjun. Iodine-Mediated Synthesis of 2-Acylquinoline from Acetophenone and 2-(Arylvinyl)aniline[J]. Chinese Journal of Organic Chemistry, ;2020, 40(5): 1337-1344. doi: 10.6023/cjoc201911029 shu

Iodine-Mediated Synthesis of 2-Acylquinoline from Acetophenone and 2-(Arylvinyl)aniline

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Corresponding author: Wang Xicun, wangxicun@nwnu.edu.cn Quan Zhengjun, quanzhengjun@hotmail.com
Received Date: 24 November 2019
Revised Date: 9 January 2020
Available Online: 15 January 2020
Fund Project: the National Natural Science Foundation of China 21562036Project supported by the National Natural Science Foundation of China (No. 21562036)

Figures(2)

The cyclization reaction between 2-(arylvinyl)aniline and acetophenone in presence of iodine was reported, which offered an efficient and cost effective strategy to generate 2-acylquinoline derivatives under mild and metal-free conditions.
- 2-(arylvinyl) aniline,
- acetophenone,
- 2-acylquinoline,
- metal-free
1. [1]
  (a) Solomon, V. R.; Haq, W.; Srivastava, K.; Puri, S. K.; Katti, S. B. J. Med. Chem. 2007, 50, 394.
  (b) Michael, J. P. Nat. Prod. Rep. 2007, 24, 223.
  (c) Bharate, J. B.; Vishwakarma, R. A.; Bharate, S. B. RSC Adv. 2015, 5, 42020.
  (d) Solomon, V. R.; Lee, H. Curr. Med. Chem. 2011, 18, 1488.
  (e) Singh, S.; Kaur, G.; Mangla, V.; Gupta, M. K. J. Enzyme Inhib. Med. Chem. 2015, 30, 492.
  (f) Afzal, O.; Kumar, S.; Haider, M. R.; Ali, M. R.; Kumar, R.; Jaggi, M.; Bawa, S. Eur. J. Med. Chem. 2015, 97, 871.
  (g) Andries, K.; Verhasselt, P.; Guillemont, J.; Cambau, E.; Truffot-Pernot, C.; Lounis, N.; Jarlier, V. Science 2005, 307, 223.
  (h) Behenna, D. C.; Stockdill, J. L.; Stoltz, B. M. Angew. Chem., Int. Ed. 2008, 47, 2365.
2. [2]
  (a) Rouffet, M.; F.de Oliveira, C. A.; Udi, Y.; Agrawal, A.; Sagi, I.; McCammon, J. A.; Cohen, S. M. J. Am. Chem. Soc. 2010, 132, 8232.
  (b) Kim, J. I.; Shin, I. S.; Kim, H.; Lee, J. K. J. Am. Chem. Soc. 2005, 127, 1614.
  (c) Bhalla, V.; Vij, V.; Kumar, M.; Sharma, P. R.; Kaur, T. Org. Lett. 2012, 14, 1012.
  (d) Tao, S.; Li, L.; Yu, J.; Jiang, Y.; Zhou, Y.; Lee, C. S.; Lee, S. T.; Zhang, X.; Kwon, O. Chem. Mater. 2009, 21, 1284.
  (e) Wang, M.; Shi, Y. H.; Luo, J. F.; Du, W.; Shi, X. X.; Fossey, J. S.; Deng, W.-P. Catal. Sci. Technol. 2011, 1, 100.
  (f) Wang, M.; Wang, Z.; Shi, Y. H.; Shi, X. X.; Fossey, J. S.; Deng, W. P. Angew. Chem., Int. Ed. 2011, 50, 4897.
  (g) Wang, Z.; Yu, X.; Tian, B. X.; Payne, D. T.; Yang, W. L.; Liu, Y. Z.; Fossey, J. S.; Deng, W. P. Chem.-Eur. J. 2015, 21, 10457.
  (h) Ma, C.; Fang, P.; Mei, T. S. ACS Catal. 2018, 8, 7179.
  (i) Nimmagadda, S. K.; Liu, M. Y.; Karunananda, M. K.; Gao, D. W.; Apolinar, O.; Chen, J. S.; Liu, P.; Engle, K. M. Angew. Chem., Int. Ed. 2019, 58, 3923.
  (j) Takamatsu, K.; Hirano, K.; Miura, M.; Angew. Chem., Int. Ed. 2017, 56, 5353.
  (k) Barday, M.; Janot, C.; Halcovitch, N. R.; Muir, J.; Aissa, C. Angew. Chem., Int. Ed. 2017, 56, 13117.
3. [3]
  (a) Yao, R.; Rong, G.; Yan, B.; Qiu, L.; Xu X. ACS Catal. 2016, 6, 1024.
  (b) Wang, Q.; Huang, J.; Zhou, L. Adv. Synth. Catal. 2015, 357, 2479.
  (c) Zhang, L.; Chen, Su.; Gao, Y.; Zhang, P.; Wu, Y.; Tang, G.; Zhao, Y. Org. Lett. 2016, 18, 1286.
  (d) Jiang, H.; An, X.; Tong, K.; Zheng, T.; Zhang, Y.; Yu, S. Angew. Chem., Int. Ed. 2015, 54, 4055.
  (e) Zhou, W.; Lei, J. Chem. Commun. 2014, 50, 5583.
  (f) Li, H.; Wang, C.; Huang, H.; Xu, X.; Li, Y. Tetrahedron Lett. 2011, 52, 1108.
  (g) Matsubara, Y.; Hirakawa, S.; Yamaguchi, Y.; Yoshida, Z. I. Angew. Chem., Int. Ed. 2011, 50, 7670.
  (h) Xu, P.; Zhu, T.; Wei, T.; Wang, S.; Ji, S. RSC Adv. 2016, 6, 32467.
  (i) Zheng, W. P.; Yang, W. G.; Luo, D. P.; Min, L.; Wang, X. Y.; Hu, Y. F. Adv. Synth. Catal. 2019, 361 1995.
  (j) Ye, J. L.; Zhu, Y. N.; Geng, H.; Huang, P. Q. Sci. China Chem. 2018, 61, 687.
4. [4]
  (a) Corey, E. J.; Tramontano, A. J. Am. Chem. Soc. 1981, 103, 5599.
  (b) Laras, Y.; Hugues, V.; Chandrasekaran, Y.; Blanchard-Desce, M.; Acher, F. C.; Pietrancosta, N. J. Org. Chem. 2012, 77, 8294.
  (c) Wu, Y. C.; Liu, L.; Li, H. J.; Wang, D.; Chen, Y. J. J. Org. Chem. 2006, 71, 6592.
5. [5]
  (a) Bergstroem, F. W. Chem. Rev. 1944, 35, 77.
  (b) Coscia, A. T.; Dickerman, S. C. J. Am. Chem. Soc. 1959, 81, 3098.
6. [6]
  (a) Bello, D.; Ramon, R.; Lavilla, R. Curr. Org. Chem. 2010, 14, 332.
  (b) Kouznetsov, V. V. Tetrahedron 2009, 65, 2721.
7. [7]
  Wei, W. T.; Teng, F.; Li, Y.; Song, R. J.; Li, J. H. Org. Lett. 2019, 21, 6285. doi: 10.1021/acs.orglett.9b02169
8. [8]
  Zheng, J.; Li, Z.; Huang, L. B.; Wu, W. Q.; Li, J. X.; Jiang, H. F. Org. Lett. 2016, 18, 3514. doi: 10.1021/acs.orglett.6b01008
9. [9]
  Chen, P.; Nan, J.; Hu, Y.; Ma, Q.; Ma, Y. M. Org. Lett. 2019, 21, 4812. doi: 10.1021/acs.orglett.9b01702
10. [10]
  (a) Hirupathi, N.; Puri, S.; Reddy, T. J.; Sridhar, B.; Reddy, M. S. Adv. Synth. Catal. 2016, 358, 303.
  (b) Gadakh, S. K.; Dey, S.; Sudalai, A. Org. Biomol. Chem. 2016, 14, 2969.
  (c) Zheng, L.; Guo, B.; Hua, R. J. Org. Chem. 2014, 79, 11541.
  (d) Gu, Z. Y.; Liu, C. G.; Wang, S. Y.; Ji, S. J. Org. Lett. 2016, 18, 2379.
  (e) Wei, W. T.; Cheng, Y. J.; Hu, Y.; Chen, Y. Y; Zhang, X. J.; Zou, Y.; Yan, M. Adv. Synth. Catal. 2015, 357, 3474.
  (f) Bao, L.; Liu, J. L.; Xu, L.; Hu, Z. Y.; Xu, X. X. Adv. Synth. Catal. 2018, 360, 1870.
11. [11]
  (a) Wu, X.; Geng, X.; Zhao, P.; Zhang, J. J.; Gong, X. X.; Wu, Y. D.; Wu, A. X. Org. Lett. 2017, 19, 1550.
  (b) Geng, X.; Wu, X.; Zhao, P.; Zhang, J. J.; Wu, Y. D.; Wu, A. X. Org. Lett. 2017, 19, 4179.
  (c) Geng, X.; Wang, C.; Zhao, P.; Zhou, Y.; Wu, Y. D.; Wu, A. X. Org. Lett. 2019, 21, 4939.
  (d) Gao, Q. H.; Liu, S.; Wu, X.; Wu, A. X. Org. Lett. 2014, 16, 4582.
12. [12]
  (a) Zhang, X.; Wang, T. L.; Huo, C. D.; Wang, X. C.; Quan, Z. J. Chem. Commun. 2018, 54, 3114.
  (b) Wang, T. L.; Liu, X. J.; Huo, C. D.; Wang, X. C.; Quan, Z. J. Chem. Commun. 2018, 54, 499.
  (c) Zhang, X.; Wang, T. L.; Liu, X. J.; Wang, X. C.; Quan, Z. J. Org. Biomol. Chem. 2019, 17, 2379.
  (d) Wang, T. L.; Liu, X. J.; Zhang, X.; Cao, B. Q.; Quan, Z. J.; Wang, X. C. Tetrahedron Lett. 2018, 59, 4426.
  (e) Cao, B. Q.; Qiu, Y. F.; Zhang, X.; Zhu, Z. H.; Quan, Z. J.; Wang, X. C. Eur. J. Org. Chem. 2019, 2019, 1208.
13. [13]
  (a) Li, D. J.; Zeng, F. L. Org. Lett., 2017, 19, 6498.
  (b) Zhu, J. W.; Hu, W. M.; Sun, S.; Yu, J. T.; Cheng, J. Adv. Synth. Catal. 2017, 359, 3725.
  (c) Huang, Y. N.; Li, Y. L.; Li, J.; Deng, J. J. Org. Chem. 2016, 81, 4645.
  (d) Ferguson, J.; Zeng, F. L.; Alwis, N.; Alper, H. Org. Lett. 2013, 15, 1998.
  (e) Pang, X. B.; Wu, M. Z.; Ni, J. X.; Zhang, F. M.; Lan, J. F.; Chen, B. H.; Yan, R. L. J. Org. Chem. 2017, 82, 10110.
  (f) Zhang, Z.; Liao, L. L.; Yan, S. S.; Wang, L.; He, Y. Q.; Ye, J. H.; Li, J.; Zhi, Y. G.; Yu, D. G. Angew. Chem., Int. Ed. 2016, 55, 7068.
  (h) Zhang, X.; Xu, X. F.; Yu, L. T.; Zhao, Q. Tetrahedron Lett. 2014, 55, 2280.
  (g) Sun, S.; Zhou, C.; Yu, J. T.; Cheng, J. Org. Lett. 2019, 21, 6579.
  (h) Ni, J. X.; Jiang, Y.; An, Z. Y.; Yan, R. L. Org. Lett. 2018, 20, 1534.
14. [14]
  (a) Čubiňák, M.; Eigner, V.; Tobrman, T. Adv. Synth. Catal. 2018, 360, 4604.
  (b) Isley, N. A.; Wang, Y.; Gallou, F.; Handa, S.; Aue, D. H.; Lipshutz, B. H. ACS Catal. 2017, 7, 8331.
  (c) Walker, B. R.; Sevov, C. S. ACS Catal. 2019, 9, 7197.
  (d) Gruß, H.; Belu, C.; Bernhard, L. M.; Merschel, A.; Sewald, N. Chem.-Eur. J. 2019, 25, 5880.
  (e) Yan, B.; Zhou, Y. B.; Zhang, H.; Chen, J. J.; Liu, Y. H. J. Org. Chem. 2007, 72, 7783.
  (f) Smith, C. R.; Bunnelle, E. M.; Rhodes, A. J.; Sarpong, R. Org. Lett. 2007, 9, 1169.
15. [15]
  (a) Deshidi, R.; Devari, S.; Shah, B. A. Org. Chem. Front. 2015, 2, 515.
  (b) Zhu, Y. P.; Liu, M. C.; Jia, F. C.; Yuan, J. J.; Gao, Q. H.; Lian, M.; Wu, A. X. Org. Lett. 2012, 14, 3392.
  (c) Kornblum, N.; Jones, W. J.; Anderson, G. J. J. Am. Chem. Soc. 1959, 81, 4113.
  (d) Kornblum, N.; Powers, J. W.; Anderson, G. J.; Jones, W.J.; Larson, H. O.; Levand, O.; Weaver, W. M. J. Am. Chem. Soc. 1957, 79, 6562.
  (e) Monga, A.; Bagchi, S.; Sharma, A. New J. Chem. 2018, 42, 1551.
  (f) Mohammed, S.; Vishwakarma, R. A.; Bharate, S. B. J. Org. Chem., 2015, 80, 6915.
  (g) Yan, R. L.; Yan, H.; Ma, C.; Ren, Z. Y.; Gao, X. A.; Huang, G. S.; Liang, Y. M. J. Org. Chem. 2012, 77, 2024.
  (h) An, Z. Y.; Jiang, Y.; Guan, X.; Yan, R. L. Chem. Commun. 2018, 54, 10738.
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