Citation: Chunhua Ma, Mengjiao Liu, Siyu Ouyang, Zhenwei Cui, Jingjing Bi, Yuqin Jiang, Zhiguo Zhang. Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water[J]. Chinese Chemical Letters, ;2025, 36(1): 109755. doi: 10.1016/j.cclet.2024.109755 shu

Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water

Chunhua Ma ^{a, *,} ,
Mengjiao Liu ^a ,
Siyu Ouyang ^a ,
Zhenwei Cui ^b ,
Jingjing Bi ^a ,
Yuqin Jiang ^{a, *,} ,
Zhiguo Zhang ^{a, *,}

a.
Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Engineering Research Centre of Chiral Hydroxyl Pharmaceutical, Henan Engineering Laboratory of Chemical Pharmaceutical and Biomedical Materials, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China
b.
Chongqing Aoshe Bio-chemical Co. Ltd., Chongqing 400000, China

2016007@htu.edu.cn

jiangyuqin@htu.edu.cn

zhangzg@htu.edu.cn

Received Date: 21 December 2023
Revised Date: 23 February 2024
Accepted Date: 5 March 2024
Available Online: 9 March 2024

Figures(6)

A transition-metal- and oxidant-free amination/cyclization reaction to access 1,2,4-triazolo[1,5-a]pyridines was realized in water by using amino diphenylphosphinate as amino source. A broad array of readily accessible N-(pyridyl)amides could be converted into the products featuring a diverse set of functional groups. The sustainable methodology was successfully applied to the late-stage functionalization of natural products and drugs.
- 1,2,4-Triazolo[1,5-a]pyridines,
- On water,
- N-(Pyridyl)amides,
- Cyclization,
- Metal-free
1. [1]
  M.C. Bryan, B. Dillon, L.G. Hamann, et al., J. Med. Chem. 56 (2013) 6007–6021. doi: 10.1021/jm400250p
2. [2]
  J.Y. Chen, J. Huang, K. Sun, W.M. He, Org. Chem. Front. 9 (2022) 1152–1164. doi: 10.1039/D1QO01504D
3. [3]
  Y. Lang, C.J. Li, H. Zeng, Org. Chem. Front. 8 (2021) 3594–3613. doi: 10.1039/d1qo00359c
4. [4]
  X.Y. Yuan, F.L. Zeng, H.L. Zhu, et al., Org. Chem. Front. 7 (2020) 1884–1889. doi: 10.1039/d0qo00222d
5. [5]
  E. Vitaku, D.T. Smith, J.T. Njardarson, J. Med. Chem. 57 (2014) 10257–10274. doi: 10.1021/jm501100b
6. [6]
  C. Ma, Q. Li, M. Zhao, et al., J. Med. Chem. 64 (2021) 16242–16270. doi: 10.1021/acs.jmedchem.1c01559
7. [7]
  L.D. Pennington, D.T. Moustakas, J. Med. Chem. 60 (2017) 3552–3579. doi: 10.1021/acs.jmedchem.6b01807
8. [8]
  M.N.R. Ashfold, J.P. Goss, B.L. Green, et al., Chem. Rev. 120 (2020) 5745–5794. doi: 10.1021/acs.chemrev.9b00518
9. [9]
  C. Hamdouchi, P. Maiti, A.M. Warshawsky, et al., J. Med. Chem. 61 (2018) 934–945. doi: 10.1021/acs.jmedchem.7b01411
10. [10]
  C.H. Jin, M. Krishnaiah, D. Sreenu, et al., J. Med. Chem. 57 (2014) 4213–4238. doi: 10.1021/jm500115w
11. [11]
  J. Larsen, M. Lambert, H. Pettersson, et al., J. Med. Chem. 63 (2020) 14502–14521. doi: 10.1021/acs.jmedchem.0c00797
12. [12]
  S. Ahmed, A. Ayscough, G.R. Barker, et al., J. Med. Chem. 60 (2017) 5663–5672. doi: 10.1021/acs.jmedchem.7b00352
13. [13]
  S. Ueda, H. Nagasawa, J. Am. Chem. Soc. 131 (2009) 15080–15081. doi: 10.1021/ja905056z
14. [14]
  X. Meng, C. Yu, P. Zhao, RSC Adv. 4 (2014) 8612–8616. doi: 10.1039/c3ra47029f
15. [15]
  J. Xia, X. Huang, M. Cai, Synthesis 51 (2019) 2014–2022. doi: 10.1055/s-0037-1611712
16. [16]
  Z. Zheng, S. Ma, L. Tang, et al., J. Org. Chem. 79 (2014) 4687–4693. doi: 10.1021/jo500298j
17. [17]
  L. Song, X. Tian, Z. Lv, et al., J. Org. Chem. 80 (2015) 7219–7225. doi: 10.1021/acs.joc.5b01183
18. [18]
  A. Bhatt, R.K. Singh, B.K. Sarma, R. Kant, Tetrahedron Lett. 60 (2019) 151026. doi: 10.1016/j.tetlet.2019.151026
19. [19]
  Y. Li, Z. Ye, N. Chen, Z. Chen, F. Zhang, Green Chem. 21 (2019) 4035–4039. doi: 10.1039/c9gc01895f
20. [20]
  B. Li, P.H. Dixneuf, Chem. Soc. Rev. 42 (2013) 5744–5767. doi: 10.1039/c3cs60020c
21. [21]
  M. Cortes-Clerget, J. Yu, J.R.A. Kincaid, et al., Chem. Sci. 12 (2021) 4237–4266. doi: 10.1039/d0sc06000c
22. [22]
  W.T. Ouyang, F. Xiao, L.J. Ou, W.M. He, Curr. Opin. Green Sust. 40 (2023) 100760. doi: 10.1016/j.cogsc.2023.100760
23. [23]
  L.Y. Xie, S. Peng, F. Liu, et al., ACS Sustain. Chem. Eng. 7 (2019) 7193–7199. doi: 10.1021/acssuschemeng.9b00200
24. [24]
  S. Peng, Y.X. Song, J.Y. He, et al., Chin. Chem. Lett. 30 (2019) 2287–2290. doi: 10.1016/j.cclet.2019.08.002
25. [25]
  L.Y. Xie, S. Peng, J.X. Tan, et al., ACS Sustain. Chem. Eng. 6 (2018) 16976–16981. doi: 10.1021/acssuschemeng.8b04339
26. [26]
  L.Y. Xie, Y.J. Li, J. Qu, et al., Green Chem. 19 (2017) 5642–5646. doi: 10.1039/C7GC02304A
27. [27]
  S.S. Zhu, L. Zuo, Y. Liu, B. Yu, Green Chem. 24 (2022) 8725–8732. doi: 10.1039/d2gc02950b
28. [28]
  L. Tang, Y. Ouyang, K. Sun, B. Yu, RSC Adv. 12 (2022) 19736–19740. doi: 10.1039/d2ra03467k
29. [29]
  X.Y. Li, Y. Liu, X.L. Chen, et al., Green Chem. 22 (2020) 4445–4449. doi: 10.1039/c9gc04445k
30. [30]
  F. Li, L. Lu, J. Ma, Org. Chem. Front. 2 (2015) 1589–1597. doi: 10.1039/C5QO00255A
31. [31]
  B. Lin, X. Zhang, C.Y. Zhou, C.M. Che, Org. Chem. Front. 8 (2021) 1216–1222. doi: 10.1039/d0qo01266a
32. [32]
  X. Liu, W.Z. Dong, Y. Li, et al., Org. Chem. Front. 10 (2023) 355–362. doi: 10.1039/d2qo01541b
33. [33]
  D. Ye, R. Huang, H. Zhu, L.H. Zou, D. Wang, Org. Chem. Front. 6 (2019) 62–69. doi: 10.1039/c8qo00941d
34. [34]
  Z. Zhang, L. Ji, X. Liu, et al., Org. Chem. Front. 9 (2022) 5154–5159. doi: 10.1039/d2qo01081j
35. [35]
  J.K. Laha, A. Gupta, U. Gulati, et al., Org. Chem. Front. 9 (2022) 6902–6908. doi: 10.1039/d2qo01465c
36. [36]
  M.A. Morozova, M.S. Yusubov, B. Kratochvil, et al., Org. Chem. Front. 4 (2017) 978–985. doi: 10.1039/C6QO00787B
37. [37]
  W. Shi, C. Yang, L. Guo, W. Xia, Org. Chem. Front. 9 (2022) 6513–6519. doi: 10.1039/d2qo01424f
38. [38]
  S. Liu, Y. Zhou, Y. Sui, H. Liu, H. Zhou, Org. Chem. Front. 4 (2017) 2175–2178. doi: 10.1039/C7QO00604G
39. [39]
  J. Zhen, Y. Li, H. Yuan, et al., Org. Chem. Front. 10 (2023) 404–409. doi: 10.1039/d2qo01429g
40. [40]
  S. Xu, P. Wu, W. Zhang, Org. Biomol. Chem. 14 (2016) 11389–11395. doi: 10.1039/C6OB02200F
41. [41]
  M. Liu, F. Zhou, Z. Jia, C.J. Li, Org. Chem. Front. 1 (2014) 161–166. doi: 10.1039/c3qo00063j
42. [42]
  S. Liu, P. Zhang, Y. Zhang, et al., Org. Chem. Front. 8 (2021) 5858–5865. doi: 10.1039/d1qo01068a
43. [43]
  H.X. Song, Q.Y. Han, C.L. Zhao, C.P. Zhang, Green Chem. 20 (2018) 1662–1731. doi: 10.1039/c8gc00078f
44. [44]
  P. Norcott, C. Spielman, C.S.P. McErlean, Green Chem. 14 (2012) 605–609. doi: 10.1039/c2gc16259h
45. [45]
  J. Tomasek, J. Schatz, Green Chem. 15 (2013) 2317–2338. doi: 10.1039/c3gc41042k
46. [46]
  D.N. Kommi, P.S. Jadhavar, D. Kumar, A.K. Chakraborti, Green Chem. 15 (2013) 798–810. doi: 10.1039/c3gc37004f
47. [47]
  Y.H. Lu, Z.T. Zhang, H.Y. Wu, et al., Chin. Chem. Lett. 34 (2023) 108036. doi: 10.1016/j.cclet.2022.108036
48. [48]
  S. Laulhé, S.S. Gori, M.H. Nantz, J. Org. Chem. 77 (2012) 9334–9337. doi: 10.1021/jo301133y
49. [49]
  J.A. Smulik, E. Vedejs, Org. Lett. 5 (2003) 4187–4190. doi: 10.1021/ol035629w
50. [50]
  A. Armstrong, R.D.C. Pullin, C.R. Jenner, J.N. Scutt, J. Org. Chem. 75 (2010) 3499–3502. doi: 10.1021/jo100407s
51. [51]
  A. Armstrong, C.A. Baxter, S.G. Lamont, A.R. Pape, R. Wincewicz, Org. Lett. 9 (2007) 351–353. doi: 10.1021/ol062852v
52. [52]
  M. Ong, M. Arnold, A.W. Walz, J.M. Wahl, Org. Lett. 24 (2022) 6171–6175. doi: 10.1021/acs.orglett.2c02361
53. [53]
  C. Ma, Z. Feng, J. Li, et al., Org. Chem. Front. 8 (2021) 3286–3291. doi: 10.1039/d1qo00064k
54. [54]
  C.H. Ma, L. Zhao, X. He, Y.Q. Jiang, B. Yu, Org. Chem. Front. 9 (2022) 1445–1450. doi: 10.1039/d1qo01870a
55. [55]
  C.H. Ma, M. Chen, Z.W. Feng, et al., New J. Chem. 45 (2021) 9302–9314. doi: 10.1039/d1nj00704a
56. [56]
  C.H. Ma, Y. Ji, J. Zhao, et al., Chin. J. Catal. 43 (2022) 571–583. doi: 10.1016/S1872-2067(21)63917-7
57. [57]
  C. Ma, Y. Tian, J. Wang, et al., Org. Lett. 24 (2022) 8265–8270. doi: 10.1021/acs.orglett.2c02949
58. [58]
  C. Ma, H. Meng, J. Li, et al., Chin. J. Chem. 40 (2022) 2655–2662. doi: 10.1002/cjoc.202200386
59. [59]
  Y.Q. Jiang, J. Li, Z.W. Feng, et al., Adv. Synth. Catal. 362 (2020) 2609–2614. doi: 10.1002/adsc.202000233
60. [60]
  C. Ma, X. Li, X. Chen, et al., Org. Lett. 25 (2023) 8016–8021. doi: 10.1021/acs.orglett.3c03193
61. [61]
  W. Klötzer, H. Baldinger, E.M. Karpitschka, J. Knoflach, Synthesis 1982 (1982) 592–595. doi: 10.1055/s-1982-29875
62. [62]
  M. Fernández, R. Alonso, Org. Lett. 5 (2003) 2461–2464. doi: 10.1021/ol034696n
63. [63]
  A.G. Draffan, B. Frey, B. Pool, et al., ACS Med. Chem. Lett. 5 (2014) 679–684. doi: 10.1021/ml500077j
64. [64]
  A. Armstrong, R.D.C. Pullin, C.R. Jenner, et al., Tetrahedron: Asymmetry 25 (2014) 74–86. doi: 10.1016/j.tetasy.2013.11.008
65. [65]
  J.S.W. Klötzer, J. Raneburger, Org. Synth. 64 (1986) 96. doi: 10.15227/orgsyn.064.0096
66. [66]
  H. Hikawa, M. Imani, H. Suzuki, Y. Yokoyama, I. Azumaya, RSC Adv. 4 (2014) 3768–3773. doi: 10.1039/C3RA46749J
67. [67]
  A.K. Sharma, P. Sharma, P. Mehara, P. Das, Chem. Eng. J. 471 (2023) 144666. doi: 10.1016/j.cej.2023.144666
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