Citation: Xiaochun Liu, Gaoyan Chen, Xiaodong Yue, Chaoyue Wang, Xue-Xin Zhang, Xuecheng Ran, Yingxiao Zong, Junke Wang, Xicun Wang. A novel N-stable Co₂P nano-catalyst for the synthesis of quinoxalines by annulation of alkynes and 1,2-diaminobenzenes[J]. Chinese Chemical Letters, ;2025, 36(8): 110707. doi: 10.1016/j.cclet.2024.110707 shu

A novel N-stable Co₂P nano-catalyst for the synthesis of quinoxalines by annulation of alkynes and 1,2-diaminobenzenes

Xiaochun Liu ^{a, b, 1} ,
Gaoyan Chen ^{b, 1} ,
Xiaodong Yue ^{a, b} ,
Chaoyue Wang ^c ,
Xue-Xin Zhang ^b ,
Xuecheng Ran ^b ,
Yingxiao Zong ^{b, *,} ,
Junke Wang ^{a, b, d, *,} ,
Xicun Wang ^{a, *,}

a.
Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China
b.
Key Laboratory of Hexi Corridor Resources Utilization of Gansu, College of Chemistry and Chemical Engineering, Hexi University, Zhangye 734000, China
c.
Key Laboratory of Opto-Electronic Technology and Intelligent Control (Ministry of Education), Lanzhou Jiaotong University, Lanzhou 730070, China
d.
Hubei Key Laboratory of Processing and Application of Catalytic materials, Huanggang Normal University, Huanggang 438000, China

zongyx@hxu.edu.cn

wangjk@hxu.edu.cn

wangxicun@nwnu.edu.cn

Received Date: 21 September 2024
Revised Date: 26 November 2024
Accepted Date: 2 December 2024
Available Online: 4 December 2024

Figures(7)

Designing efficient, recyclable, and low-cost catalysts is crucial for the synthesis of quinoxaline derivatives. In this context, a novel N-stable Co₂P nano-catalyst (CoP@NC-1.5) was developed using a template-sacrificial approach. The catalyst demonstrated a broad substrate scope and good functional group tolerance, achieving yields of up to 84%. Additionally, the catalyst exhibited reusability and can be recycled up to three times. The CoP@NC-1.5 was characterized using X-ray powder diffraction (XRD), scanning electron microscopy (SEM), and transmission electron microscopy (TEM). The results indicated that the catalyst contained Co₂P nanoparticles. The X-ray photoelectron spectroscopy (XPS) further confirms the presence of Co-P. Analysis of the characterization data and experimental results revealed that the active site of the catalyst comprises N-stable Co₂P nanoparticles.
- Annulations,
- Nano-catalyst,
- Quinoxaline,
- Nanomaterials,
- Heterogeneous
1. [1]
  A.K. Parhi, Y. Zhang, K.W. Saionz, et al., Bioorg. Med. Chem. Lett. 23 (2013) 4968–4974.
2. [2]
  A. Zeb, A. Hameed, L. Khan, et al., Med. Chem. 10 (2014) 724–729. doi: 10.2174/1573406410666140526145429
3. [3]
  S.T. Hazeldine, L. Polin, J. Kushner, et al., J. Med. Chem. 44 (2001) 1758–1776.
4. [4]
  R.A. Smits, H.D. Lim, A. Hanzer, et al., J. Med. Chem. 51 (2008) 2457–2467. doi: 10.1021/jm7014217
5. [5]
  Y.B. Kim, Y.H. Kim, J.Y. Park, S.K. Kim, Bioorg. Med. Chem. Lett. 14 (2004) 541–544.
6. [6]
  S. Tariq, K. Somakala, M. Amir, Eur. J. Med. Chem. 143 (2018) 542–557.
7. [7]
  S. Ammermann, C. Hrib, P.G. Jones, et al., Org. Lett. 14 (2012) 5090–5093. doi: 10.1021/ol302348v
8. [8]
  L. Wang, W. Guo, X.X. Zhang, X.D. Xia, W.J. Xiao, Org. Lett. 14 (2012) 740–743. doi: 10.1021/ol203275b
9. [9]
  W. Wang, Y. Shen, X. Meng, et al., Org. Lett. 13 (2011) 4514–4517. doi: 10.1021/ol201664x
10. [10]
  J. Yuan, J. Ouyang, V. Cimrová, et al., J. Mater. Chem. C 5 (2017) 1858–1879.
11. [11]
  H. Khatoon, E. Abdulmalek, Molecules 26 (2021) 1055. doi: 10.3390/molecules26041055
12. [12]
  V.K. Maikhuri, A.K. Prasad, A. Jha, S. Srivastav, New J. Chem. 45 (2021) 13214–13246. doi: 10.1039/d1nj01442k
13. [13]
  L. Biesena, T.J.J. Müller, Adv. Synth. Catal. 363 (2021) 980–1006.
14. [14]
  J. Gao, Z.G. Ren, J.P. Lang, Chin. Chem. Lett. 28 (2017) 1087–1092.
15. [15]
  A. Kumar, T.M. Dhameliya, R.V. Hirani, A.J. Bhatt, J. Mol. Struct. 1259 (2022) 132732.
16. [16]
  Y. Xu, X. Wan, Tetrahedron Lett. 54 (2013) 642–645.
17. [17]
  S. Shi, T. Wang, W. Yang, M. Rudolph, A.S.K. Hashmi, Chem. Eur. J. 19 (2013) 6576–6580. doi: 10.1002/chem.201300518
18. [18]
  S.A. Jadhav, A.P. Sarkate, M.G. Shioorkar, D.B. Shinde, Synth. Commun. 47 (2017) 1661–1667. doi: 10.1080/00397911.2017.1337153
19. [19]
  C.F. Gers-Panther, H. Fischer, J. Nordmann, et al., J. Org. Chem. 82 (2016) 567–578.
20. [20]
  H.R. Yang, Z.Y. Hu, X.C. Li, L. Wu, X.X. Guo, Org. Lett. 24 (2022) 8392–8396. doi: 10.1021/acs.orglett.2c03465
21. [21]
  J. Zi, D.W. Gu, Y. Zhang, et al., Synth. Commun. 48 (2018) 915–920. doi: 10.1080/00397911.2018.1428752
22. [22]
  W. Zhang, X. Yang, Z. Cao, et al., ChemistrySelect 8 (2023) e202302634.
23. [23]
  A. Das, K.R.J. Thomas, Asian J. Org. Chem. 9 (2020) 1820–1825. doi: 10.1002/ajoc.202000388
24. [24]
  J.V. Obligacion, P.J. Chirik, Nature Rev. Chem. 2 (2018) 15–34. doi: 10.1038/s41570-018-0001-2
25. [25]
  P. Gandeepan, T. Müller, D. Zell, et al., Chem. Rev. 119 (2019) 2192–2452. doi: 10.1021/acs.chemrev.8b00507
26. [26]
  W. Fang, T. Tu, Sci. China Chem. 66 (2023) 299–300. doi: 10.1007/s11426-022-1457-1
27. [27]
  W.J. Li, Z.Q. Wang, J.B. Wang, et al., J. Catal. 430 (2024) 115308.
28. [28]
  F. Ghaffarian, M.A. Ghasemzadeh, S.S. Aghaei, J. Mol. Struct. 1186 (2019) 204–211.
29. [29]
  Q.H. Liu, S.L. Kang, Z.S. Cui, et al., Green Chem. 26 (2024) 4803–4810. doi: 10.1039/d4gc00502c
30. [30]
  J. Safaei-Ghomi, M.A. Ghasemzadeh, A. Kakavand-Qalenoei, J. Saudi Chem. Soc. 20 (2016) 502–509. doi: 10.1016/j.jscs.2012.07.010
31. [31]
  R. Bakhshali-Dehkordi, M.A. Ghasemzadeh, J. Safaei-Ghomi, J. Mol. Struct. 1216 (2020) 127698.
32. [32]
  J.S. Ghomi, S. Zahedi, M.A. Ghasemzadeh, Monatsh. Chem. 145 (2014) 1191–1199.
33. [33]
  J.S. Ghomi, S. Zahedi, M.A. Ghasemzadeh, Res. Chem. Intermed. 41 (2015) 8625–8636.
34. [34]
  H.Y. Song, J. Jiang, C. Wu, et al., Green Chem. 25 (2023) 3292–3296. doi: 10.1039/d2gc04843d
35. [35]
  Y.H. Lu, C. Wu, J.C. Hou, et al., ACS Catal. 13 (2023) 13071–13076. doi: 10.1021/acscatal.3c02268
36. [36]
  S. Mekki, Y. Laichi, F. Benourrad, et al., Appl. Organomet. Chem. 37 (2023) e7103.
37. [37]
  A. Bharathi, S.M. Roopan, A. Kajbafvala, et al., Chin. Chem. Lett. 25 (2014) 324–326.
38. [38]
  A.V. Nakhate, K.B. Rasal, G.P. Deshmukh, S.S.R. Gupta, L.K. Mannepalli, J. Chem. Sci. 129 (2017) 1761–1769. doi: 10.1007/s12039-017-1393-0
39. [39]
  Z. Wang, G. Hu, J. Liu, et al., Chem. Comm. 51 (2015) 5069–5072.
40. [40]
  H. Ye, J. Shi, Y. Wu, et al., Fuel 356 (2024) 129594.
41. [41]
  M. Ashraf, M.S. Ahmad, Y. Inomata, et al., Coord. Chem. Rev. 476 (2023) 214928.
42. [42]
  J. Hou, M. Kazemi, Res. Chem. Intermed. 50 (2024) 1713–1743. doi: 10.1007/s11164-024-05243-3
43. [43]
  B. Maleki, H. Esmaeili, Renew Energy 209 (2023) 10–26.
44. [44]
  J. Wang, Y. Zong, X. Wang, et al., Green Chem. 18 (2016) 967–973.
45. [45]
  X. Liu, C. Wang, J. Meng, et al., Chin. Chem. Lett. 34 (2023) 108745.
46. [46]
  B. You, N. Jiang, M. Sheng, et al., Chem. Mater. 27 (2015) 7636–7642. doi: 10.1021/acs.chemmater.5b02877
47. [47]
  H. Liu, J. Guan, S. Yang, et al., Adv. Mater. 32 (2020) 2003649.
48. [48]
  J. Song, C. Zhu, B.Z. Xu, et al., Adv. Energy Mater. 7 (2017) 1601555.
49. [49]
  L. Huang, H. Zhang, Y. Cheng, et al., Chin. Chem. Lett. 33 (2022) 2569–2572.
50. [50]
  J.M. Stillahn, K.J. Trevino, E.R. Fisher, ACS Appl. Mater. Interfaces 3 (2011) 1402–1410. doi: 10.1021/am101282y
51. [51]
  H.H. Wang, N. Leaukosol, Z.B. He, P. Navard, Cellulose 20 (2013) 1587–1601. doi: 10.1007/s10570-013-9945-z
52. [52]
  X. Li, Y. He, S. Cheng, et al., Adv. Mater. 33 (2021) 2106371.
53. [53]
  D. Xi, J. Li, J. Low, et al., Adv. Mater. 34 (2022) 2104090.
54. [54]
  M. Li, H. Wang, W. Luo, et al., Adv. Mater. 32 (2020) 2001848.
55. [55]
  X. Hu, D. Zhou, H. Wang, et al., Chin. Chem. Lett. 34 (2023) 108050.
56. [56]
  H. Liu, P. Zhu, D. Yang, et al., J. Am. Chem. Soc. 146 (2024) 2132–2140. doi: 10.1021/jacs.3c11632
57. [57]
  Q. Zhu, F. Wang, F. Zhang, Z. Dong, Nanoscale 11 (2019) 17736–17745. doi: 10.1039/c9nr04867g
1. [1]
  Yanyu Jin , Wenzhe Si , Xing Yuan , Hongjun Cheng , Bin Zhou , Li Cai , Yu Wang , Qibao Wang , Junhua Li . Tuning TM–O interaction by acid etching in perovskite catalysts boosting catalytic performance. Chinese Chemical Letters, 2025, 36(5): 110260-. doi: 10.1016/j.cclet.2024.110260
2. [2]
  Miao-Miao Chen , Min-Ling Zhang , Xiao Song , Jun Jiang , Xiaoqian Tang , Qi Zhang , Xiuhua Zhang , Peiwu Li . Smartphone-assisted electrochemiluminescence imaging test strips towards dual-signal visualized and sensitive monitoring of aflatoxin B1 in corn samples. Chinese Chemical Letters, 2025, 36(1): 109785-. doi: 10.1016/j.cclet.2024.109785
3. [3]
  Xu Luo , Jinwen Xiao , Qiming Yang , Xiaolong Lu , Qianjun Huang , Xiaojun Ai , Bo Li , Li Sun , Long Chen . Biomaterials for surgical repair of osteoporotic bone defects. Chinese Chemical Letters, 2025, 36(1): 109684-. doi: 10.1016/j.cclet.2024.109684
4. [4]
  Xiaoyu Zhang , Xin Yu . Solar-powered heterogeneous water disinfection nano-system. Chinese Journal of Structural Chemistry, 2025, 44(3): 100439-100439. doi: 10.1016/j.cjsc.2024.100439
5. [5]
  Zunyuan Xie , Lijin Yang , Zixiao Wan , Xiaoyu Liu , Yushan He . Exploration of the Preparation and Characterization of Nano Barium Titanate and Its Application in Inorganic Chemistry Laboratory Teaching. University Chemistry, 2024, 39(4): 62-69. doi: 10.3866/PKU.DXHX202310137
6. [6]
  Simin Fang , Wei Huang , Guanghua Yu , Cong Wei , Mingli Gao , Guangshui Li , Hongjun Tian , Wan Li . Integrating Science and Education in a Comprehensive Chemistry Design Experiment: The Preparation of Copper(I) Oxide Nanoparticles and Its Application in Dye Water Remediation. University Chemistry, 2024, 39(8): 282-289. doi: 10.3866/PKU.DXHX202401023
7. [7]
  Haoyu Luo , Jinsong Chen , Mengfei Luo , Hui Ma , Shengyan Pu . Heterogeneous Fenton catalytic degradation of nitrobenzene by controlled-release nano calcium peroxide. Chinese Chemical Letters, 2025, 36(6): 110367-. doi: 10.1016/j.cclet.2024.110367
8. [8]
  Wen-Jing Li , Jun-Bo Wang , Yu-Heng Liu , Mo Zhang , Zhan-Hui Zhang . Molybdenum-doped carbon nitride as an efficient heterogeneous catalyst for direct amination of nitroarenes with arylboronic acids. Chinese Chemical Letters, 2025, 36(3): 110001-. doi: 10.1016/j.cclet.2024.110001
9. [9]
  Xuling Pan , Wei Cai , You Huang . Recent advances in phosphine-mediated sequential annulations. Chinese Chemical Letters, 2025, 36(5): 110628-. doi: 10.1016/j.cclet.2024.110628
10. [10]
  Weichen Zhu , Wei Zuo , Pu Wang , Wei Zhan , Jun Zhang , Lipin Li , Yu Tian , Hong Qi , Rui Huang . Fe-N-C heterogeneous Fenton-like catalyst for the degradation of tetracycline: Fe-N coordination and mechanism studies. Chinese Chemical Letters, 2024, 35(9): 109341-. doi: 10.1016/j.cclet.2023.109341
11. [11]
  Yimin Guo , Yiting Luo , Shuwen Hua , Chuan-Fan Ding , Yinghua Yan . Application of magnetic nanomaterials in peptidomics: A review in the past decade. Chinese Chemical Letters, 2025, 36(6): 110070-. doi: 10.1016/j.cclet.2024.110070
12. [12]
  Ke Wu , Xiuqin Ruan , Shuolei Jia , Enyuan Wang , Qingfa Zhou . DABCO-catalyzed [3+4] annulations of Schiff bases with α-substituted allenes: Construction of functionalized benzazepine derivatives. Chinese Chemical Letters, 2025, 36(7): 110646-. doi: 10.1016/j.cclet.2024.110646
13. [13]
  Ningxiang Wu , Huaping Zhao , Yong Lei . Nanomaterials with highly ordered nanostructures: Definition, influence and future challenge. Chinese Journal of Structural Chemistry, 2024, 43(11): 100392-100392. doi: 10.1016/j.cjsc.2024.100392
14. [14]
  Jiangshan Xu , Weifei Zhang , Zhengwen Cai , Yong Li , Long Bai , Shaojingya Gao , Qiang Sun , Yunfeng Lin . Tetrahedron DNA nanostructure/iron-based nanomaterials for combined tumor therapy. Chinese Chemical Letters, 2024, 35(11): 109620-. doi: 10.1016/j.cclet.2024.109620
15. [15]
  Di An , Mingdong She , Ziyang Zhang , Ting Zhang , Miaomiao Xu , Jinjun Shao , Qian Shen , Xuna Tang . Light-responsive nanomaterials for biofilm removal in root canal treatment. Chinese Chemical Letters, 2025, 36(2): 109841-. doi: 10.1016/j.cclet.2024.109841
16. [16]
  Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257
17. [17]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
18. [18]
  Shuai Tang , Zian Wang , Mengyi Zhu , Xinyun Zhao , Xiaoyun Hu , Hua Zhang . Synthesis of organoboron compounds via heterogeneous C–H and C–X borylation. Chinese Chemical Letters, 2025, 36(5): 110503-. doi: 10.1016/j.cclet.2024.110503
19. [19]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
20. [20]
  Di Wang , Qing-Song Chen , Yi-Ran Lin , Yun-Xin Hou , Wei Han , Juan Yang , Xin Li , Zhen-Hai Wen . Tuning strategies and electrolyzer design for Bi-based nanomaterials towards efficient CO2 reduction to formic acid. Chinese Journal of Structural Chemistry, 2024, 43(8): 100346-100346. doi: 10.1016/j.cjsc.2024.100346

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(17)
HTML views(1)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

A novel N-stable Co2P nano-catalyst for the synthesis of quinoxalines by annulation of alkynes and 1,2-diaminobenzenes

Metrics

通讯作者: 陈斌, bchen63@163.com

A novel N-stable Co₂P nano-catalyst for the synthesis of quinoxalines by annulation of alkynes and 1,2-diaminobenzenes