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Igneous rock powder as a heterogeneous multi-oxide nano-catalyst for the synthesis of 5-substituted-1H-tetrazoles in polyethylene glycol

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Abstract

The use of igneous rock nano-powder as a heterogeneous and recyclable multi-oxide nano-catalyst synthesizing of 5-substituted-1H-tetrazoles is reported. The igneous rock nano-powder was initially prepared by using the ball-milling method. Then, the structure, morphology, and magnetic properties of the prepared igneous rock nano-powder were characterized with some different spectroscopic, microscopic, and thermogravimetric techniques, such as FTIR, FESEM, XRF, XRD, Histogram, and EDS. The instrumental analyses showed that the prepared igneous rock powder is a mixture of metal oxides, such as Si, Al, Ca, Mg, Fe, Na, Mn, and Sr. It showed an excellent catalytic performance in synthesizing of 5-substituted-1H-tetrazoles through [3 + 2] cycloaddition reaction between sodium azide and nitrile compounds. Various aliphatic and aromatic nitriles and sodium azide were reacted in the presence of a catalytic amount of igneous rock nano-powder at 80 o C temperature in PEG-400. The protocol was simple and rapid, with suitable yields of the obtained tetrazoles. The igneous rock nano-powder is readily accessible, reusable, and holds potential for further application in acid-catalyzed organic syntheses and industrial requirements.

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References

  1. R. Gill, Igneous Rocks and Processes: A Practical Guide (Wiley, Chichester, West Sussex, 2011)

    Google Scholar 

  2. W. Jinghong, Z. Caineng, J. Jiuqiang, Z. Rukai, Pet. Explor. Dev. 38, 708–715 (2011)

    Article  Google Scholar 

  3. R.W. Le Maitre (ed.), Igneous rocks: A Classification and glossary of terms (Cambridge University Press, Cambridge, 2002)

    Google Scholar 

  4. S. Nockolds, Geol. Soc. Am. Bull. 65, 1007–1032 (1954)

    Article  CAS  Google Scholar 

  5. C.P. Thornton, O.F. Tuttle, Am. J. Sci. 258, 664–684 (1960)

    Article  CAS  Google Scholar 

  6. L.S. Walter, J.W. Salisbury, J. Geophys. Res.: Solid Earth. 94, 9203–9213 (1989)

    Article  CAS  Google Scholar 

  7. M.G. Siani, D.R. Lentz, M. Nazarian, Ore Geol. Rev. 126, 103753 (2020)

    Article  Google Scholar 

  8. J. Tarney, C. Jones, J. Geol. Soc. 151, 855–868 (1994)

    Article  CAS  Google Scholar 

  9. V.M. Chubarov, A.L. Finkelshtein, Spectrochim Acta, Part B 107, 110–114 (2015)

    Article  CAS  Google Scholar 

  10. A. Sarvary, A. Maleki, Mol. Divers. 19, 189–212 (2015)

    Article  CAS  PubMed  Google Scholar 

  11. V.V. Dhayabaran, I.S. Lydia, J.P. Merlin, P. Srirenganayaki, Ionics 10, 123–125 (2004)

    Article  CAS  Google Scholar 

  12. A. Mariyam, M. Shahid, I. Mantasha, M.S. Khan, M.S. Ahmad, J. Inorg. Organomet. Polym. Mater. 30, 1935–1943 (2020)

    Article  CAS  Google Scholar 

  13. G. Aridoss, K.K. Laali, Eur. J. Org. Chem. 2011, 6343–6355 (2011)

    Article  CAS  Google Scholar 

  14. E.N. Lushin, R.A. Castro, Key Eng. Mater. 723, 459–463 (2017)

    Article  Google Scholar 

  15. Y. Qiang, H. Li, X. Lan, J. Mater. Sci. Technol. 52, 63–71 (2020)

    Article  Google Scholar 

  16. P. Politzer, J.S. Murray (eds.), Energetic materials: Part 2. Detonation, Combustion (Elsevier, Amsterdam, 2003)

    Google Scholar 

  17. W.-H. Ding, W. Cao, X.-J. Zheng, W.-J. Ding, J.-P. Qiao, L.-P. Jin, Dalton Trans. 43, 6429–6435 (2014)

    Article  CAS  PubMed  Google Scholar 

  18. C.G. Neochoritis, T. Zhao, A. Dömling, Chem. Rev. 119, 1970–2042 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. N. Fischer, K. Karaghiosoff, T.M. Klapötke, J. Stierstorfer, New energetic materials featuring tetrazoles and nitramines–synthesis, characterization and properties, Wiley Online Library, (2010)

  20. J. Bladin, Ber. Dtsch. Chem. Ges. 18, 1544–1551 (1885)

    Article  Google Scholar 

  21. Z.P. Demko, K.B. Sharpless, J. Org. Chem. 66, 7945–7950 (2001)

    Article  CAS  PubMed  Google Scholar 

  22. P. Movaheditabar, M. Javaherian, Org. Chem. Res. 5, 174–189 (2019)

    Google Scholar 

  23. P. Movaheditabar, M. Javaherian, V. Nobakht, React. Kinet., Mech. Catal. 122, 217–228 (2017)

    Article  CAS  Google Scholar 

  24. P. Moradi, A. Ghorbani-Choghamarani, Appl. Organomet. Chem. 31, e3602 (2017)

    Article  CAS  Google Scholar 

  25. S.S. Ghodsinia, B. Akhlaghinia, RSC Adv. 5, 49849–49860 (2015)

    Article  CAS  Google Scholar 

  26. N. Razavi, B. Akhlaghinia, RSC Adv. 5, 12372–12381 (2015)

    Article  CAS  Google Scholar 

  27. T. Tamoradi, A. Ghorbani-Choghamarani, M. Ghadermazi, Solid State Sci. 88, 81–94 (2019)

    Article  CAS  Google Scholar 

  28. B. Das, C.R. Reddy, D.N. Kumar, M. Krishnaiah, R. Narender, Synlett 2010, 391–394 (2010)

    Article  CAS  Google Scholar 

  29. P. Akbarzadeh, N. Koukabi, E. Kolvari, Mol. Divers. 24, 319–333 (2020)

    Article  CAS  PubMed  Google Scholar 

  30. M. Zarghani, B. Akhlaghinia, RSC Adv. 6, 31850–31860 (2016)

    Article  CAS  Google Scholar 

  31. M. Nasrollahzadeh, Y. Bayat, D. Habibi, S. Moshaee, Tetrahedron Lett. 50, 4435–4438 (2009)

    Article  CAS  Google Scholar 

  32. M. Hosseini-Sarvari, S. Najafvand-Derikvandi, C. R. Chim. 17, 1007–1012 (2014)

    Article  CAS  Google Scholar 

  33. A.N. Chermahini, A. Teimouri, A. Moaddeli, Heteroat. Chem. 22, 168–173 (2011)

    Article  CAS  Google Scholar 

  34. M.L. Kantam, K.S. Kumar, K.P. Raja, J. Mol. Catal. A: Chem. 247, 186–188 (2006)

    Article  CAS  Google Scholar 

  35. S.M. Sajadi, M. Naderi, S. Babadoust, Nat Sci Res. 1, 10–17 (2011)

    Google Scholar 

  36. M. Ai, L. Lang, B. Li, Z. Xu, Chem. Lett. 41, 814–816 (2012)

    Article  CAS  Google Scholar 

  37. J. He, B. Li, F. Chen, Z. Xu, G. Yin, J. Mol. Catal. A: Chem. 304, 135–138 (2009)

    Article  CAS  Google Scholar 

  38. B. Sreedhar, A.S. Kumar, D. Yada, Tetrahedron Lett. 52, 3565–3569 (2011)

    Article  CAS  Google Scholar 

  39. F. Abrishami, M. Ebrahimikia, F. Rafiee, Appl. Organomet. Chem. 29, 730–735 (2015)

    Article  CAS  Google Scholar 

  40. G.A. Meshram, S.S. Deshpande, P.A. Wagh, V.A. Vala, Tetrahedron Lett. 55, 3557–3560 (2014)

    Article  CAS  Google Scholar 

  41. N. Moeini, T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Appl. Organomet. Chem. 32, e4445 (2018)

    Article  CAS  Google Scholar 

  42. G. Sandhya Rani, A. Jyotsna, B.L. Prabhavathi Devi, Asian J. Green Chem. 3, 125–136 (2019)

    Google Scholar 

  43. R. Jahanshahi, B. Akhlaghinia, Rsc Adv. 5, 104087–104094 (2015)

    Article  CAS  Google Scholar 

  44. J.-J. Shie, J.-M. Fang, J. Org. Chem. 68, 1158–1160 (2003)

    Article  CAS  PubMed  Google Scholar 

  45. J.V. Duncia, M.E. Pierce, J.B. Santella III., J. Org. Chem. 56, 2395–2400 (1991)

    Article  CAS  Google Scholar 

  46. J.-J. Shie, J.-M. Fang, J. Org. Chem. 72, 3141–3144 (2007)

    Article  CAS  PubMed  Google Scholar 

  47. A. Vignesh, N.S. Bhuvanesh, N. Dharmaraj, J. Org. Chem. 82, 887–892 (2017)

    Article  CAS  PubMed  Google Scholar 

  48. M. Javaherian, F. Kazemi, M. Ghaemi, Chin. Chem. Lett. 25, 1643–1647 (2014)

    Article  CAS  Google Scholar 

  49. M. Yazdanian, Heterocycl. Lett. 8, 277–285 (2018)

    CAS  Google Scholar 

  50. U. Aroke, A. Abdulkarim, R. Ogubunka, ATBU. J. Environ. Technol. 6, 42–53 (2013)

    Google Scholar 

  51. J. Chen, S.K. Spear, J.G. Huddleston, R.D. Rogers, Green Chem. 7, 64–82 (2005)

    Article  CAS  Google Scholar 

  52. B. Salahshournia, H. Hamadi, V. Nobakht, Appl. Organomet. Chem. 32, e4416 (2018)

    Article  CAS  Google Scholar 

  53. Z. Du, C. Si, Y. Li, Y. Wang, J. Lu, Int. J. Mol. Sci. 13, 4696–4703 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  54. L.E. Cárdenas-Galindo, A. Islas-Jácome, C.J. Cortes-García, L. El Kaim, R. Gámez-Montaño, J. Mex. Chem. Soc. 57, 283–289 (2013)

    Google Scholar 

  55. A.R. Modarresi-Alam, M. Nasrollahzadeh, Turk. J. Chem. 33, 267–280 (2009)

    CAS  Google Scholar 

  56. H.M. Nanjundaswamy, H. Abrahamse, Heterocycles 89, 2137–2150 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This study was supported by the committee grant of the Shahid Chamran University of Ahvaz No. SCU.SC99.440. The authors gratefully thank this support.

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Correspondence to Mohammad Javaherian.

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All of authors have been received research grants from Department of Chemistry, Faculty of Science, Shahid Chamran University of Ahvaz, Ahvaz, Iran. On behalf of all authors, the corresponding author states that there is no conflict of interest.

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Movaheditabar, P., Javaherian, M. & Nobakht, V. Igneous rock powder as a heterogeneous multi-oxide nano-catalyst for the synthesis of 5-substituted-1H-tetrazoles in polyethylene glycol. J IRAN CHEM SOC 19, 1805–1816 (2022). https://doi.org/10.1007/s13738-021-02421-7

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  • DOI: https://doi.org/10.1007/s13738-021-02421-7

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