Synthesis of nitrogen rich 5-substituted-1H-tetrazoles using a heterogeneous magnetic catalyst based on zirconium

Document Type : Original Article

Authors

1 Faculty of Chemistry and Chemical Engineering, Malek-Ashtar University of Technology

2 .Faculty of Chemistry and Chemical Engineering, Malek-Ashtar University of Technology

3 Department of Chemistry, Estahban Higher Education Center, Estahban, Iran

10.22036/cr.2022.337345.1179

Abstract

Tetrazoles are an important class of nitrogen-rich heterocycles which have a wide range of applications in high energy materials, pharmaceutical industries, treatment of various disease, biochemistry, bioimaging, and photography. In this paper, Zr0.25Zn0.25Cu0.5Fe2O4 catalyst was first synthesized by two common combustion and hydrothermal methods and was then characterized by inductively coupled plasma atomic emission spectroscopy (ICP-AES), X-ray diffraction (XRD) and field emission scanning electron microscopy (FE-SEM) methods. Furthermore, this catalyst has the magnetic properties. The catalytic activity of the Zr0.25Zn0.25Cu0.5Fe2O4 heterogeneous magnetic catalyst was investigated for the synthesis of a wide range of 5-substituted-1H-tetrazole derivatives via [3+2] cycloaddition of sodium azide with various nitriles in N,N-dimethylformamide at 120 °C. The main advantages of this method are high efficiency, simple methodology, easy work-up and catalyst reusability. Furthermore, this catalyst can be easily separated from the reaction mixture using an external magnet and reused for five cycles without a significant decrease in its catalytic activity.

Graphical Abstract

Synthesis of nitrogen rich 5-substituted-1H-tetrazoles using a heterogeneous magnetic catalyst based on zirconium

Keywords

Main Subjects

References

  1. Roh, G. Karabanovich, H. Vlčková, A. Carazo, J. Němeček, P. Sychra, L. Valášková, O. Pavliš, J. Stolaříková, V. Klimešová, K. Vávrová, P. Pávek, A. Hrabálek, Bioorg. Med. Chem. 25, 5468 (2017).
  2. S. Dofe, A. P. Sarkate, S. H. Kathwate, C. H. Gill, Heterocycl. Commun. 23, 325 (2017).
  3. Zhang, S. Wang, Y. Ba, Z. Xu, Eur. J. Med. Chem. 178, 341 (2019).
  4. N. Dhiman, K. Kaur, V. Jaitak, Med. Chem. 28, 11559 (2020).
  5. Ramakrishna, R. S. Leela, L. K. Ravindranath, Med. Chem. (Los Angeles), 7, 239 (2017).
  6. Sharma, M. C. Sharma, D. V. Kohli, J. Optoelectron. Biomed. Mater. 1, 59 (2010).
  7. Bielenica, D. Szulczyk, W. Olejarz, S. Madeddu, G. Giliberti, I. B. Materek, A. E. Koziol, M. Struga, Biomed. Pharmacother. 94, 804 (2017).
  8. Zhan, H. Liu, X. Liu, Y. Wang, C. Pannecouque, M. Witvrouw, E. De Clercq, Med. Chem. Res. 19, 652 (2010).
  9. A. Abu-Hashem, M. El-Shazly, Polycycl. Aromat. Compd. 41, 478 (2021).
  10. Łukowska-Chojnacka, J. Mierzejewska, M. Milner-Krawczyk, M. Bondaryk, M. Staniszewska, Bioorg. Med. Chem. 24, 6058 (2016).
  11. Qian, Y. Zheng, R. Wang, J. Wei, Y. Cui, X. Cao, Y. Yang, Bioorg. Med. Chem. Lett. 28, 344 (2018).
  12. F. Lamie, J. N. Philoppes, A. A. Azouz, N. M. Safwat, J. Enzyme Inhib. Med. Chem. 32, 805 (2017).
  13. B. Labib, A. M. Fayez, E. -S. EL-Nahass, M. Awadallah, P. A. Halim, Bioorg. Chem. 104, 104308 (2020).
  14. E. Ford, P. Knowles, E. Lunt, S. M. Marshall, A. J. Penrose, C. A. Ramsden, A. J. Summers, J. L. Walker, D. E. Wright, J. Med. Chem. 29, 538 (1986).
  15. E. Ford, P. Knowles, E. Lunt, S. M. Marshall, A. J. Penrose, C. A. Ramsden, A. J. H. Summers, J. L. Walker, Derek E. Wright, J. Med. Chem. 29, 538 (1986).
  16. V. Faria, M. S. dos Santos, A. M. R. Bernardino, K. M. Becker, G. M. C. Machado, R. F. Rodrigues, M. M. Canto-Cavalheiro, L. L. Leon, Bioorg. Med. Chem. Lett. 23, 6310 (2013).
  17. Dileep, S. Polepalli, N. Jain, S. K. Buddana, R. S. Prakasham, M. S. R. Murty, Mol. Divers. 22, 83 (2018).
  18. Gao, J. Xiao, G. Huang, Eur. J. Med. Chem. 184, 111744 (2019).
  19. Swami, S. N. Sahu, R. Shrivastava, RSC Adv. 11, 39058 (2021).
  20. A. Ostrovskii, M. S. Pevzner, T. P. Kofman, M. B. Shcherbinin, I. V. Tselinskii, Targets Heterocycl. Syst. 3, 497 (1999).
  21. Ponnuvel, V. Padmini, R. Sribalan, Sens. Actuator B-Chem. 222, 625 (2016).
  22. -H. Ding, W. Cao, X. -J. Zheng, W. -J. Ding, J. -P. Qiao, L. -P. Jin, Dalton Trans. 43, 6429 (2014).
  23. Szimhardt, M. H. H. Wurzenberger, P. Spieß, T. M. Klapötke, J. Stierstorfer, Propellants, Explos. Pyrotech. 43, 1203 (2018).
  24. Manzoor, Q. Tariq, X.Yin, J. -G. Zhang, Def. Technol. 17, 1995 (2021).
  25. -G. Xu,Y. -F. Yan, X. -Z. Li, F. -K. Zheng, G. -C. Guo, Chem. Eng. J. 429, 132451 (2022).
  26. Zhang, D. Chen, D. Jing, G. Fan, L. He, H. Li , W. Wang, F. Nie, Green Chem. 21, 1947 (2019).
  27. Karaghiosoff, T. M. Klapötke, C. M. Sabaté, Eur. J. Inorg. Chem. 2009, 238 (2009).
  28. He, J. -G. Zhang, X. Yin, J. -T. Wu, L. Wu, Z. -N. Zhou, T. -L. Zhang, Chem. Eur. J. 22, 7670 (2016).
  29. Steinhauser, T. M. Klapötke, Angew. Chem. Int. Ed. 47, 3330 (2008).
  30. Hantzsch, A. Vagt, Justus Liebigs Ann. Chem. 314, 339 (1901).
  31. J. Wittenberger, B. G. Donner, J. Org. Chem. 58, 4139 (1993).
  32. Duncia, M. E. Pierce, J. B. Santella, J. Org. Chem. 56, 2395 (1991).
  33. P. Demko, K.B. Sharpless, J. Org. Chem. 66, 7945 (2001).
  34. P. Demko, K. B. Sharpless, Org. Lett. 4, 2525 (2002).
  35. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo, L. Vaccoro, J. Org. Chem. 69, 2896 (2004).
  36. Nasrollahzadeh, N. Motahharifar, Z. Nezafat, M. R. Shokouhimehr, Colloids Interface Sci. Commun. 44, 100471 (2021).
  37. Lang, B. Li, W. Liu, L. Jiang, Z. Xu, G. Yin, Chem. Commun. 46, 448 (2010).
  38. Coca, E. Turek, Tetrahedron Lett. 55, 2718 (2014).
  39. Mani, A. K. Singh, S. K. Awasthi, Tetrahedron Lett. 55, 1879 (2014).
  40. M. Nanjundaswamy, H. Abrahamse, Heterocycles 89, 2137 (2014).
  41. Kumar, S. Dubey, N. Saxena, S. K. Awasthi, Tetrahedron Lett. 55, 6034 (2014).
  42. S. E. Ghodsinia, B. Akhlaghinia, RSC Adv. 5, 49849 (2015).
  43. Taheri Kal-Koshvandi, A. Maleki, A. Tarlani, M. Rahim Soroush, ChemistrySelect 5, 3164 (2020).
  44. Habibi, M. Nasrollahzadeha, T. A. Kamali, Green Chem. 13, 3499 (2011).
  45. Jahanshahi, B. Akhlaghinia, RSC Adv. 5, 104087 (2015).
  46. Esirden, E. Erken, M. Kaya, F. Sen, Catal. Sci. Technol. 5, 4452 (2015).
  47. Kumar, R. Narayanan, H. Shechter, J. Org. Chem. 61, 4462 (1996).
  48. Venkateshwarlu, A. Premalatha, K. C. Rajanna, P. K. Saiprakash, Synth. Commun. 39, 4479 (2009).
  49. Bonnamour, C. Bolm, Chem. Eur. J. 15, 4543 (2009).
  50. Y. Wani, A. R.Bhat, A. Azam, I. Choi, F. Athar, Eur. J. Med. Chem. 48, 313 (2012).
  51. Rama, K. Kanagaraj, K. Pitchumani, J. Org. Chem. 76, 9090 (2011).
  52. R. Patil, M. B. Deshmukh, D. S. Dalal, J. Iran. Chem. Soc. 9, 799 (2012).
  53. Nammalwar, N. Prasad Muddala, R. Pitchimani, R. A. Bunce, Molecules 20, 22757 (2015).
  54. L. Heilmann, E. J. W. Verwey, J. Chem. Phys. 15, 174 (1947).
  55. M. Lu, W. T. Zheng, Q. Jiang, J. Phys. D: Appl. Phys. 40, 320 (2007).
  56. Teimouri, A. Najafi Chermahini, Polyhedron 30, 2606 (2011).
  57. Abrishami, M. Ebrahimikia, F. Rafiee, Appl. Organomet. Chem. 29 730 (2015).
  58. Wagner, J. Org. Chem. 38, 2976 (1973).
  59. Shie, J. Fang, J. Org. Chem. 72, 31241 (2007).
  60. R. Katritzky, C. Cai, N. K. Meher, Synthesis 8, 1204 (2007).
  61. Kong, Y. Liu, J. Zhang, H. Li, X Wang, G. Liu, B. Li, Z. Xu, New J. Chem. 38, 3078 (2014).
  62. Dimitriev, Y. Ivanova, R. IordanovaJ. Univ. Chem. Technol. Metallurgy 43, 181 (2008).
  63. Li, S.Y. Chen, J. J. Li, H. Wang, A. S. Hernandez, S. Tao, J. Med. Chem. 50, 5890 (2007).

 

 

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History

  • Receive Date: 16 April 2022
  • Revise Date: 24 July 2022
  • Accept Date: 16 September 2022

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