Citation: Zhang Bianxiang, Kang Yongqiang, Shi Ruixue. Synthesis of Aromatic Heterocyclic Sulfide Compounds[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1814-1823. doi: 10.6023/cjoc201602021 shu

Synthesis of Aromatic Heterocyclic Sulfide Compounds

1.
School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006

Corresponding author: Zhang Bianxiang, zbxthh@sxu.edu.cn
Received Date: 22 February 2016
Revised Date: 25 March 2016

Fund Project: Project supported by the Science and Technology Innovation Project of Shanxi Province No. 2014101011

Figures(16)

Recently, the aromatic heterocyclic sulfide was widely used in medical and functional materials as an intermediate in organic chemistry and a structural unit in drug synthesis. Their synthetic method has become one of the hot research areas. This review summarizes the recent synthetic methods of aromatic heterocyclic thioether, which mainly involves metallic catalyzed and no metal-catalyzed methods, as well as benzene alkyne intermediate method. Some of their synthetic mechanisms were illustrated.
- aromatic heterocyclic sulfide,
- metal catalysis,
- benzene intermediate
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
  Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 13.
6. [6]
  Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Chem. Soc. Jpn. 1980, 53, 1385.(b) Murahashi, S.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408.(c) Foa, M.; Santi, R.; Garavaglia, F. J. Organomet. Chem. 1981, 206, C29.
7. [7]
  Dickens, M. J.; Gilday, J. P.; Mowlem, T. J.; Widdowson, D. A. Tetrahedron 1991, 47, 8621.
8. [8]
  Guo, Y. J.; Tang, R. Y.; Li, J. H.; Zhong, P.; Zhang, X. G. Adv. Synth. Catal. 2009, 351, 2615.
9. [9]
  Wu, G. L.; Liu, Q.; Shen, Y. L.; Wu, W. T.; Wu, L. M. Tetrahedron Lett. 2005, 46, 5831.(b) Schlosser, K. M.; Krasutsky, A. P.; Hamilton, H. W.; Reed, J. E.; Sexton, K. Org. Lett. 2004, 6, 819.(c) La Regina, G.; Edler, M. C.; Brancale, A.; Kandil, S.; Coluccia, A.; Piscitelli, F.; Hamel, E.; De Martino, G.; Matesanz, R.; Diaz, J. F.; Scovassi, A. I.; Prosperi, E.; Lavecchia, A.; Novellino, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2007, 50, 2865.(d) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.(e) Yadav, J. S.; Reddy, B. V. S.; Reddy, Y. J. Tetrahedron Lett. 2007, 48, 7034.
10. [10]
  Chen, Y.; Cho, C. H.; Shi, F.; Larock, R. C. J. Org. Chem. 2009, 74, 6802.
11. [11]
  Anbarasan, P.; Neumann, H.; Beller, M. Chem. Commun. 2011, 47, 3233.
12. [12]
  Cong, M.; Fan, Y.; Raimundo, J.-M.; Xia, Y.; Liu, Y.; Quelever, G.; Qu, F.-Q.; Peng, L. Chem.-Eur. J. 2013, 19, 17267.(b) Cong, M.; Fan, Y.; Raimundo, J.-M.; Tang, J.; Peng, L. Org. Lett. 2014, 16, 4074.
13. [13]
  Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915.
14. [14]
  Taniguchi, N. J. Org. Chem. 2007, 72, 1241.(b) Taniguchi, N. Synlett. 2006, 1351.
15. [15]
  Luo, P.-S.; Yu, M.; Tang, R.-Y.; Zhong, P.; Li, J.-H. Tetrahedron Lett. 2009, 50, 1066.
16. [16]
  Fukuzawa, S.-I.; Shimizu, E.; Atsuumi, Y.; Haga, M.; Ogata, K. Tetrahedron Lett. 2009, 50, 2374.
17. [17]
  Ranjit, S.; Lee, R.; Heryadi, D.; Shen, C.; Wu, J.; Zhang, P.; Hang, K. W.; Liu, X. J. Org. Chem. 2011, 76, 8999.
18. [18]
  Dai, C.; Xu, Z.; Huang, F.; Yu, Z.; Gao, Y.-F. J. Org. Chem. 2012, 77, 4414.
19. [19]
  He, Z.; Luo, F.; Li, Y.; Zhu, G. Tetrahedron Lett. 2013, 54, 5907.
20. [20]
  Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. Org. Lett. 2011, 13, 454.
21. [21]
  Alves, D.; Lara, R. G.; Contreira, M. E.; Radatz, C. S.; Duarte, L. F. B.; Perin, G. Tetrahedron Lett. 2012, 53, 3364.
22. [22]
  He, G.; Huang, Y.; Tong, Y.; Zhang, J.; Zhao, D.; Zhou, S.; Han, S. Tetrahedron Lett. 2013, 54, 5318.
23. [23]
24. [24]
  Jiang, X. F.; Qiao, Z. J. CN 104725172A, 2015 [Chem. Abstr. 2015, 163, 191616].
25. [25]
  Singh, N.; Singh, R.; Raghuvanshi, D. S.; Singh, K. N. Org. Lett. 2013, 15, 5874.
26. [26]
27. [27]
  Taniguchi, N. J. Org. Chem. 2004, 69, 6904.
28. [28]
  Gómez-Benítez, V.; Baldovino-Pantaleón, O.; Herrera-Álvarez, C.; Toscano, R. A.; Morales-Morales, D. Tetrahedron Lett. 2006, 47, 5059.
29. [29]
  Gendre, F.; Yang, M.; Diaz, P. Org. Lett. 2005, 7, 2719.
30. [30]
  Duan, Z.; Ranjit, S.; Zhang, P.; Liu, X. Chem. Eur. J. 2009, 15, 3666.
31. [31]
  Wang, P.-F.; Wang, X.-Q.; Dai, J.-J.; Feng, Y.-S.; Xu, H.-J. Org. Lett. 2014, 16, 4586.
32. [32]
  Ge, W.; Wei, Y. Green Chem. 2012, 14, 2066.
33. [33]
  Azeredo, J. B.; Godoi, M.; Martins, G. M.; Silveira, C. C.; Braga, A. L. J. Org. Chem. 2014, 79, 4125.
34. [34]
  Yang, F. L.; Tian, S. K. Angew. Chem., Int. Ed. 2013, 52, 4929.
35. [35]
  Hou, W.; Wei, Q.; Liu, G.; Chen, J.; Guo, J.; Peng, Y. Org. Lett. 2015, 17, 4870.
36. [36]
  Kitamura, T.; Zhang, B.-X.; Fujiwara, Y. J. Org. Chem. 2003, 68, 731.
37. [37]
  Wang, F.-Y.; Chen, Z.-C.; Zheng, Q.-G. J. Chem. Res. 2004, 127.
38. [38]
  Wagner, A. M.; Sanford, M. S. J. Org. Chem. 2014, 79, 2263.
39. [39]
  Zhan, H.; Cao, H.; Qiu, H.; Li, N.; Chen, L.; Liu, J.; Cai, H.; Tan, J. RSC Adv. 2015, 5, 32205.
40. [40]
41. [41]
  Shaw, E.; Bernstein, J.; Losee, K.; Lott, W. A. J. Am. Chem. Soc. 1950, 72, 4362.
42. [42]
  Singh, R.; Raghuvanshi, D. S.; Singh, K. N. Org. Lett. 2013, 15, 4202.
43. [43]
44. [44]
  Varun, B. V.; Prabhu, K. R. J. Org. Chem. 2014, 79, 9655.
45. [45]
46. [46]
  Yonova, I. M.; Osborne, C. A.; Morrissette, N. S.; Jarvo, E. R. J. Org. Chem. 2014, 79, 1947.
47. [47]
  Li, Z. J.; Sun, L.X.; Yang, L.; Zeng, Q. L. Fresen. Environ. Bull. 2015, 24, 3686.
48. [48]
  Bhunia, A.; Roy, T.; Pachfule, P.; Rajamohanan, P. R.; Biju, A. T. Angew. Chem., Int. Ed. 2013, 52, 10040.
49. [49]
  Lin, W.; Sapountzis, I.; Knochel, P. Angew. Chem. 2005, 44, 4258.
50. [50]
  Zhao, J.; Larock, R. C. J. Org. Chem. 2007, 72, 583.
51. [51]
  Toledo, F. T.; Marques, H.; Comasseto, J. V.; Raminelli, C. Tetrahedron Lett. 2007, 48, 8125.
52. [52]
  Edwards, A. J.; Willis, A. C.; Wenger, E. Organometallics 2002, 21, 1654.
53. [53]
  Dong, Y.; Liu, B.; Chen, P.; Liu, Q.; Wang, M. Angew. Chem., Int. Ed. 2014, 53, 3442.
54. [54]
  Pawliczek, M.; Garve, L. K. B.; Werz, D. B. Org. Lett. 2015, 17, 1716.
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沈阳化工大学材料科学与工程学院沈阳 110142