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An adenine-based palladium complex: a capable heterogeneous magnetic nano-catalyst for the green synthesis of the ureas in aqueous media

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Abstract

A novel adenine-based palladium nano-complex was synthesized via preparation of the Fe3O4 magnetic nano-particles (Fe3O4 MNPs), coating with tetraethyl orthosilicate, functionalization with both 3-chloropropyltrimethoxysilane (CPTMS) and adenine (AD) ligands and finally formation of the corresponding complex by PdCl2 (Fe3O4@SiO2@CPTMS@AD@ Pd). Then, it was characterized with different methods such as FT-IR, EDX, ICP, XRD, SEM, TEM, VSM and TGA-DTA techniques, and capability of the adenine-based Pd complex evaluated by its application as an efficient heterogeneous nano-catalyst for the synthesis of various N-mono-substituted ureas in water by hydrolysis of cyanamides in the presence of 98% HCOOH with good to high yields in relatively short reaction times at room temperature.

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References

  1. J.L. Ochoa, J. Porath, J. Kempf, J.M. Egly, J. Chromatog. A. 188, 257 (1980)

    Article  CAS  Google Scholar 

  2. E.J. Cho, B.J. Ryu, Y.J. Lee, K.C. Nam, Org. Lett. 7, 2607 (2005)

    Article  CAS  PubMed  Google Scholar 

  3. Y. Zhou, J.F. Zhang, J. Yoon, Chem. Rev. 114, 5511 (2014)

    Article  CAS  PubMed  Google Scholar 

  4. P.A. Gale, E.N. Howe, X. Wu, M.J. Spooner, Coord. Chem. Rev. 375, 333 (2018)

    Article  CAS  Google Scholar 

  5. T.T. Bui, H.K. Kim, Synlett 31, 997 (2020)

    Article  CAS  Google Scholar 

  6. M. Frezza, S. Castang, J. Estephane, L. Soulere, C. Deshayes, B. Chantegrel, Bioinorg. Med. Chem. 14, 4781 (2006)

    CAS  Google Scholar 

  7. A. Abad, J. Lloveras, A. Michelena, Field Crops Res. 87, 257 (2004)

    Article  Google Scholar 

  8. S. Goyal, A. Chattopadhyay, K. Kasavajhala, U.D. Priyakumar, J. Am. Chem. Soc. 139, 14931 (2017)

    Article  CAS  PubMed  Google Scholar 

  9. S.J. Choi, J.H. Lee, Y.H. Lee, D.Y. Hwang, H.D. Kim, J. Appl. Polym. Sci. 121, 3516 (2011)

    Article  CAS  Google Scholar 

  10. E.I. Pereira, F.B. Minussi, C.C. da Cruz, A.C. Bernardi, C. Ribeiro, J. Agric. Food Chem. 60, 5267 (2012)

    Article  CAS  PubMed  Google Scholar 

  11. V. Böhmer, M.O. Vysotsky, Aust. J. Chem. 54, 671 (2001)

    Google Scholar 

  12. L. Fischer, G. Guichard, Org. Biomol. Chem. 8, 3101 (2010)

    Article  CAS  PubMed  Google Scholar 

  13. C. Dou, C. Wang, H. Zhang, H. Gao, Y. Wang, Chem. Eur. J. 16, 10744 (2010)

    Article  CAS  PubMed  Google Scholar 

  14. M. Van Gool, J.M. Bartolomé, G.J. Macdonald, Tetrahedron Lett. 49, 7171 (2008)

    Article  Google Scholar 

  15. I. Gallou, Org. Prep. Proceed. Int. 39, 355 (2007)

    Article  CAS  Google Scholar 

  16. Q. Liu, N.W. Luedtke, Y. Tor, Tetrahedron Lett. 42, 1445 (2001)

    Article  CAS  Google Scholar 

  17. E. Artuso, I. Degani, R. Fochi, C. Magistris, Synthesis 2007, 3497 (2007)

    Article  Google Scholar 

  18. L. De Luca, A. Porcheddu, G. Giacomelli, I. Murgia, Synlett 2010, 2439 (2010)

    Article  Google Scholar 

  19. S. Breitler, N.J. Oldenhuis, B.P. Fors, S.L. Buchwald, Org. lett. 13, 3262 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. S.M. Sajadi, M. Maham, J. Chem. Res. 37, 623 (2013)

    Article  CAS  Google Scholar 

  21. H. Mahajan, M. Bhardwaj, S. Paul, Org. Prep. Proceed. Int. 46, 463 (2014)

    Article  CAS  Google Scholar 

  22. A.R. Sardarian, I.D. Inaloo, RSC Adv. 5, 76626 (2015)

    Article  CAS  Google Scholar 

  23. L. Wang, H. Wang, G. Li, S. Min, F. **ang, S. Liu, W. Zheng, Adv. Synth. Catal. 360, 4585 (2018)

    Article  CAS  Google Scholar 

  24. I.D. Inaloo, S. Majnooni, M. Esmaeilpour, Eur. J. Org. Chem. 26, 3481 (2018)

    Article  Google Scholar 

  25. D. Habibi, S. Heydari, A. Faraji, H. Keypour, M. Mahmoudabadi, Polyhedron 151, 520 (2018)

    Article  CAS  Google Scholar 

  26. J.A. Grzyb, M. Shen, C. Yoshina-Ishii, W. Chi, R.S. Brown, R.A. Batey, Tetrahedron 61, 7153 (2005)

    Article  CAS  Google Scholar 

  27. G. Meng, M. Wang, M.S. Dong, A.Q. Zheng, J. Shi, E. De Clercq, C. Pannecouque, J. Balzarini, Int. J. AIDS Res. 2, 19 (2015)

    Google Scholar 

  28. K. Somakala, M. Amir, Acta Pharmaceut. Sinica B 7, 230 (2017)

    Article  Google Scholar 

  29. A.R. Kulkarni, S. Garai, G.A. Thakur, J. Org. Chem. 82, 992 (2017)

    Article  CAS  PubMed  Google Scholar 

  30. M. Xu, A.R. Jupp, M.S. Ong, K.I. Burton, S.S. Chitnis, D.W. Stephan, Angew. Chem. Int. Ed. 58, 5707 (2019)

    Article  CAS  Google Scholar 

  31. V. Khorramabadi, D. Habibi, S. Heydari, Green Chem. Lett. Rev. 13, 50 (2020)

    Article  CAS  Google Scholar 

  32. N. Amirmahani, N.O. Mahmoodi, M. Malakootian, A. Pardakhty, N. Seyedi, Mater. Chem. Phys. 267, 124698 (2021)

    Article  CAS  Google Scholar 

  33. M. Mozaffari, N. Nowrouzi, Eur. J. Org. Chem. 46, 7541 (2019)

    Article  Google Scholar 

  34. D.K. Yadav, A.K. Yadav, V.P. Srivastava, G. Watal, L.D.S. Yadav, Tetrahedron Lett. 53, 2890 (2012)

    Article  CAS  Google Scholar 

  35. H.K.A. Kim, Org. Biomol. Chem. 14, 7345 (2016)

    Article  CAS  PubMed  Google Scholar 

  36. M. Patil, A.N. Poyil, S.D. Joshi, S.A. Patil, S.A. Patil, A. Bugarin, Bioorg. Chem. 87, 302 (2019)

    Article  CAS  PubMed  Google Scholar 

  37. E.V. Vinogradova, B.P. Fors, S.L. Buchwald, J. Am. Chem. Soc. 134, 11132 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Acknowledgements

We thank Bu-Ali Sina University, Hamedan Iran, for the fiscal support of this work.

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Correspondence to Davood Habibi.

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Khorram Abadi, V., Habibi, D., Heydari, S. et al. An adenine-based palladium complex: a capable heterogeneous magnetic nano-catalyst for the green synthesis of the ureas in aqueous media. J IRAN CHEM SOC 20, 1985–1996 (2023). https://doi.org/10.1007/s13738-023-02813-x

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