Citation: Yu-Shen Zhu, Linlin Shi, Lianrong Fu, Xiran Chen, Xinju Zhu, Xin-Qi Hao, Mao-Ping Song. Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles[J]. Chinese Chemical Letters, ;2022, 33(3): 1497-1500. doi: 10.1016/j.cclet.2021.08.070 shu

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles

College of Chemistry, Zhengzhou University, Zhengzhou 450001, China

xqhao@zzu.edu.cn

mpsong@zzu.edu.cn

Received Date: 14 April 2021
Revised Date: 11 August 2021
Accepted Date: 13 August 2021
Available Online: 19 August 2021

Figures(6)

A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles
- Iodine-catalyzed,
- Benzothiazoles,
- KSeCN,
- Water,
- Primary 2-benzothiazolamines
1. [1]
  M. Bhoi, M. Borad, H. Patel, Synth. Commun. 44 (2014) 2427-2457. doi: 10.1080/00397911.2014.907426
2. [2]
  M. Yoshida, I. Hayakawa, N. Hayashi, et al., Bioorg. Med. Chem. Lett. 15 (2005) 3328-3332. doi: 10.1016/j.bmcl.2005.05.077
3. [3]
  D. Fajkusova, M. Pesko, S. Keltosova, et al., J. Bioorg. Med. Chem. 20 (2012) 7059-7068. doi: 10.1016/j.bmc.2012.10.007
4. [4]
  R. Chikhale, S. Menghani, R. Babu, et al., Eur. J. Med. Chem. 96 (2015) 30-46. doi: 10.1016/j.ejmech.2015.04.011
5. [5]
  A.K. Ghosh, K.V. Rao, P.R. Nyalapatla, et al., J. Med. Chem. 60 (2017) 4267-4278. doi: 10.1021/acs.jmedchem.7b00172
6. [6]
  R.Q. Paulpandi, S. Ramasamy, M.S. Paulraj, et al., RSC Adv. 6 (2016) 15670-15677. doi: 10.1039/C6RA01202G
7. [7]
  T.L. Dadmal, S.D. Katre, M.C. Mandewale, R.M. Kumbhare, New J. Chem. 42 (2018) 776-797. doi: 10.1039/C7NJ03776G
8. [8]
  J.W. Qiu, X.G. Zhang, R.Y. Tang, P. Zhong, J.H. Li, Adv. Synth. Catal. 351 (2009) 2319-2323. doi: 10.1002/adsc.200900450
9. [9]
  Q. Ding, B. Cao, X. Liu, Z. Zhong, Y. Peng, Green Chem. 12 (2010) 1607-1610. doi: 10.1039/c0gc00123f
10. [10]
  D. Ma, X. Lu, L. Shi, et al., Angew. Chem. Int. Ed. 50 (2011) 1118-1121. doi: 10.1002/anie.201005787
11. [11]
  S.K. Sahoo, A. Banerjee, S. Chakraborty, B.K. Patel, ACS Catal. 2 (2012) 544-551. doi: 10.1021/cs200590p
12. [12]
  S. Sharma, R.S. Pathare, A.K. Maurya, et al., Org. Lett. 18 (2016) 356-359. doi: 10.1021/acs.orglett.5b03185
13. [13]
  M.Y. Gao, J.H. Li, S.B. Zhang, et al., J. Org. Chem. 85 (2020) 493-500. doi: 10.1021/acs.joc.9b02543
14. [14]
  D. Monguchi, T. Fujiwara, H. Furukawa, A. Mori, Org. Lett. 11 (2009) 1607-1610. doi: 10.1021/ol900298e
15. [15]
  S.H. Cho, J.Y. Kim, S.Y. Lee, S. Chang, Angew. Chem. Int. Ed. 48 (2009) 9127-9130. doi: 10.1002/anie.200903957
16. [16]
  J.Y. Kim, S.H. Cho, J. Joseph, S. Chang, Angew. Chem. Int. Ed. 49 (2010) 9899-9903. doi: 10.1002/anie.201005922
17. [17]
  S. Toulot, T. Heinrich, F.R. Leroux, Adv. Synth. Catal. 355 (2013) 3263-3272. doi: 10.1002/adsc.201300591
18. [18]
  Y. Zi, F. Schömberg, K. Wagner, I. Vilotijevic, Org. Lett. 22 (2020) 3407-3411. doi: 10.1021/acs.orglett.0c00882
19. [19]
  Y.Q. Zhu, R. Zhang, W. Sang, et al., Org. Chem. Front. 7 (2020) 1981-1990. doi: 10.1039/D0QO00361A
20. [20]
  S.K. Rout, S. Guin, J. Nath, B.K. Patel, Green Chem. 14 (2012) 2491-2498. doi: 10.1039/c2gc35575b
21. [21]
  Y. He, J. Li, S. Luo, J. Huang, Q. Zhu, Chem. Commun. 52 (2016) 8444-8447. doi: 10.1039/C6CC04394A
22. [22]
  Y. Xu, B. Li, X. Zhang, X. Fan, J. Org. Chem. 82 (2017) 9637-9646. doi: 10.1021/acs.joc.7b01683
23. [23]
  P. Wang, S. Tang, A. Lei, Green Chem. 19 (2017) 2092-2095. doi: 10.1039/C7GC00468K
24. [24]
  Z. Gan, G. Li, X. Yang, et al., Sci. China Chem. 63 (2020) 1652-1658. doi: 10.1007/s11426-020-9811-6
25. [25]
  M.O. Simona, C.J. Li, Chem. Soc. Rev. 41 (2012) 1415-1427. doi: 10.1039/C1CS15222J
26. [26]
  R.A. Sheldon, Chem. Soc. Rev. 41 (2012) 1437-1451. doi: 10.1039/C1CS15219J
27. [27]
  M.B. Gawande, V.D.B. Bonifacio, R. Luque, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42 (2013) 5522-5551. doi: 10.1039/c3cs60025d
28. [28]
  H. Zeng, Z. Wang, C.J. Li, Angew. Chem. Int. Ed. 58 (2019) 2859-2863. doi: 10.1002/anie.201813391
29. [29]
  X.Y. Li, Y. Liu, X.L. Chen, et al., Green Chem. 22 (2020) 4445-4449. doi: 10.1039/C9GC04445K
30. [30]
  J. Chen, T. Wang, T. Wang, et al., Org. Chem. Front. 4 (2017) 130-134. doi: 10.1039/C6QO00590J
31. [31]
  Y. Guan, S.D. Townsend, Org. Lett. 19 (2017) 5252-5255. doi: 10.1021/acs.orglett.7b02526
32. [32]
  C. Wu, H.J. Xiao, S.W. Wang, et al., ACS Sustain. Chem. Eng. 7 (2019) 2169-2175. doi: 10.1021/acssuschemeng.8b04877
33. [33]
  D. He, J. Yao, B. Ma, et al., Green Chem. 22 (2020) 1559-1564. doi: 10.1039/C9GC03797G
34. [34]
  P. Maity, D. Kundu, R. Roy, B.C. Ranu, Org. Lett. 16 (2014) 4122-4125. doi: 10.1021/ol501820e
35. [35]
  P. Maity, B. Paroi, B.C. Ranu, Org. Lett. 19 (2017) 5748-5751. doi: 10.1021/acs.orglett.7b02571
36. [36]
  T. Wang, J. Chen, J. Wang, et al., Org. Biomol. Chem. 16 (2018) 3721-3725. doi: 10.1039/C8OB00743H
37. [37]
  J. Zhu, B. Xu, J. Yu, et al., Org. Biomol. Chem. 16 (2018) 5999-6005. doi: 10.1039/C8OB01398E
38. [38]
  Y.S. Zhu, Y. Xue, W. Liu, et al., J. Org. Chem. 85 (2020) 9106-9116. doi: 10.1021/acs.joc.0c01035
39. [39]
  S. Lu, X. Zhu, K. Li, et al., J. Org. Chem. 81 (2016) 8370-8377. doi: 10.1021/acs.joc.6b01552
40. [40]
  S. Lu, Y.S. Zhu, K.X. Yan, et al., Synlett 30 (2019) 1924-1928. doi: 10.1055/s-0039-1690675
41. [41]
  Y.J. Guo, S. Lu, L.L. Tian, et al., J. Org. Chem. 83 (2018) 338-349. doi: 10.1021/acs.joc.7b02734
42. [42]
  S. Liu, R. Chen, X. Guo, et al., Green Chem. 14 (2012) 1577-1580. doi: 10.1039/c2gc35457h
43. [43]
  Y. Huang, Y. Yu, Z. Zhu, et al., J. Org. Chem. 82 (2017) 7621-7627. doi: 10.1021/acs.joc.7b00836
44. [44]
  W. Guo, W. Tan, M. Zhao, et al., J. Org. Chem. 83 (2018) 6580-6588. doi: 10.1021/acs.joc.8b00887
45. [45]
  J. Wang, B. Sun, L. Zhang, et al., Org. Chem. Front. 7 (2020) 113-118. doi: 10.1039/C9QO01055F
46. [46]
  V. Šlachtová, J. Chasák, L. Brulíková, ACS Omega 4 (2019) 19314-19323. doi: 10.1021/acsomega.9b02702
47. [47]
  S. Lu, L.L. Tian, T.W. Cui, et al., J. Org. Chem. 83 (2018) 13991-14000. doi: 10.1021/acs.joc.8b02348
48. [48]
  L.L. Tian, S. Lu, Z.H. Zhang, et al., J. Org. Chem. 84 (2019) 5213-5221. doi: 10.1021/acs.joc.9b00186
49. [49]
  Z. Yang, X. Chen, S. Wang, et al., J. Org. Chem. 77 (2012) 7086-7091. doi: 10.1021/jo300740j
50. [50]
  Y.C. Teo, S.N. Riduana, Y. Zhang, Green Chem. 15 (2013) 2365-2369. doi: 10.1039/c3gc41027g
51. [51]
  Z.J. Niu, L.H. Li, X.Y. Liu, Y.M. Liang, Adv. Synth. Catal. 361 (2019) 5217-5222. doi: 10.1002/adsc.201901078
52. [52]
  L. Wang, X. Ren, J. Yu, Y. Jiang, J. Cheng, J. Org. Chem. 78 (2013) 12076-12081. doi: 10.1021/jo402106q
53. [53]
  Y. Gao, Q. Song, G. Cheng, X. Cui, Org. Biomol. Chem. 12 (2014) 1044-1047. doi: 10.1039/C3OB42318B
54. [54]
  T.K. Achar, S. Maiti, P. Mal, Org. Biomol. Chem. 14 (2016) 4654-4663. doi: 10.1039/C6OB00532B
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