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Synthesis of Ferrocenyl Based Betti Bases by a Mannich-Type Three-Component Reaction and Investigation of Their Electrochemical Behavior

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Abstract

Ferrocenyl based Betti base derivatives, 1-[aryl(4-(4-ferrocenylbutyl)piperazin-1-yl)methyl]naphthalen-2-ol, were synthesized through one-pot three-component reaction by treatment of 1-(4-ferrocenylbutyl)piperazine, naphthalene-2-ol and benzaldehyde derivatives in ethanol as solvent in the presence of triethanolamine as catalyst under reflux condition. 1-(4-ferrocenylbutyl)piperazine was prepared by treatment of 4-chlorobutylferrocene and piperazine. Various benzaldehydes were applied to the synthesis of some new ferrocenyl Betti bases and the new ferrocenyl compounds were obtained in rather good yields (59–75%). The electrochemical performance of these new ferrocenyl based Betti bases were investigated by cyclic voltammetry in dry acetonitrile in the presence of 0.1 M LiClO4 as the electrolyte. The electrochemical studies revealed that the synthesized compounds contain a single electron quasi-reversible redox couple assigned to the ferrocenyl moiety.

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References

  1. 1.

    R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, T.A. Keating, Acc. Chem. Res. 29, 123 (1996)

  2. 2.

    A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)

  3. 3.

    A. Strecker, Ann. Chem. Pharm. 75, 27 (1850)

  4. 4.

    A.K. Bose, S. Pednekar, S.N. Ganguly, G. Chakraborty, M.S. Manhas, Tetrahedron Lett. 45, 8351 (2004)

  5. 5.

    T.A. Keating, R.W. Armstrong, J. Am. Chem. Soc. 117, 7842 (1995)

  6. 6.

    K. Kobayashi, T. Matoba, S. Irisawa, T. Matsumoto, O. Morikawa, H. Konishi, Chem. Lett. 27, 551 (1998)

  7. 7.

    G. Zhao, T. Jiang, H. Gao, B. Han, J. Huang, D. Sun, Green Chem. 6, 75 (2004)

  8. 8.

    S. Knapp, Chem. Rev. 95, 1859 (1995)

  9. 9.

    C. Cardellicchio, M.A.M. Capozzi, F. Naso, Tetrahedron Asymmetry 21, 507 (2010)

  10. 10.

    A.Y. Shen, C.T. Tsai, C.L. Chen, Eur. J. Med. Chem. 34, 877 (1999)

  11. 11.

    I. Szatmari, A. Hetenyi, L. Lazar, F. Fulop, J. Heterocycl. Chem. 41, 367 (2004)

  12. 12.

    M. Heydenreich, A. Koch, S. Klod, I. Szatmari, F. Fulop, E. Kleinpeter, Tetrahedron 62, 11081 (2006)

  13. 13.

    C. Cardellicchio, G. Ciccarella, F. Naso, F. Perna, P. Tortorella, Tetrahedron 55, 4685 (1999)

  14. 14.

    H.E. Smith, N.E. Cooper, J. Org. Chem. 35, 2212 (1970)

  15. 15.

    J. Faist, W. Seebacher, R. Saf, R. Brun, M. Kaiser, R. Weis, Eur. J. Med. Chem. 47, 510 (2012)

  16. 16.

    K. Kulig, J. Sapa, D. Maciag, B. Filipek, B. Malawska, Arch. Pharm. 340, 466 (2007)

  17. 17.

    A. Pietrzycka, M. Stepniewski, A.M. Waszkielewicz, H. Marona, Acta Pol. Pharm. 63, 19 (2006)

  18. 18.

    T.J. Kealy, P.L. Pauson, Nature 168, 1039 (1951)

  19. 19.

    J.C. Torres, R.A. Pilli, M.D. Vargas, F.A. Violante, S.J. Garden, A.C. Pinto, Tetrahedron 58, 4487 (2002)

  20. 20.

    N. Argyropoulos, E.C. Argyropoulou, J. Organomet. Chem. 654, 117 (2002)

  21. 21.

    R.D.A. Hudson, J. Organomet. Chem. 637–639, 47 (2001)

  22. 22.

    P. Naguyen, P.G. Elipe, I. Manners, Chem. Rev. 99, 1515 (1999)

  23. 23.

    I.R. Whittall, A.M. McDonagh, M.G. Humphrey, Adv. Organomet. Chem. 42, 291 (1998)

  24. 24.

    M. Uno, P.H. Dixneuf, Angew. Chem. Int. Ed. 37, 1714 (1998)

  25. 25.

    A. Togni, T. Hayashi (eds.), Ferrocenes: Homogeneous Catalysis, Organic Synthesis and Materials Science (VCH, New York, 1995)

  26. 26.

    M.F.R. Fouda, M.M. Abd-Elzaher, R.A. Abdelsamaia, A.A. Labib, Appl. Organomet. Chem. 21, 613 (2007)

  27. 27.

    S. Top, A. Vessieres, C. Cabestaing, L. Laios, G. Leclerq, C. Prorot, G. Jaouen, J. Organomet. Chem. 637–639, 500 (2001)

  28. 28.

    C. López, S. Pérez, X. Solans, M. Font-Bardía, A. Roig, E. Molins, P.W.N.M. Van Leeuwen, G.P.F. Van Strijdonck, Organometallics 26, 571 (2007)

  29. 29.

    S. Pérez, C. López, A. Caubet, X. Solans, M. Font-Bardía, A. Roig, E. Molins, Organometallics 25, 596 (2006)

  30. 30.

    A. Moyano, M. Rosol, R.M. Moreno, C. López, M.A. Maestro, Angew. Chem. Int. Ed. 44, 1865 (2005)

  31. 31.

    R.G. Arrayas, J. Adrio, J.C. Carretero, Angew. Chem. Int. Ed. 45, 7674 (2006)

  32. 32.

    C.E. Anderson, Y. Donde, D. Yariv, J. Christopher, L.E. Overman, J. Org. Chem. 70, 648 (2005)

  33. 33.

    P.N. Kelly, A. Prêtre, S. Devoy, I. O’Rielly, R. Devery, A. Goel, J.F. Gallagher, A.J. Lough, P.T.M. Kenny, J. Organomet. Chem. 692, 1327 (2007)

  34. 34.

    J.M. Lehn, Angew. Chem. Int. Ed. 29, 1304 (1990)

  35. 35.

    J.S. Miller, A.J. Epstein, Angew. Chem. Int. Ed. 33, 385 (1994)

  36. 36.

    R.P. Hanzlik, P. Soine, W.H. Soine, J. Med. Chem. 22, 424 (1979)

  37. 37.

    D. Osella, C. Nervi, F. Galeotti, G. Cavigiolio, A. Vessieres, G. Jaouen, Helv. Chim. Acta 84, 3289 (2001)

  38. 38.

    M. Inouye, M. Takase, Angew. Chem. Int. Ed. 40, 1746 (2001)

  39. 39.

    C.J. Yu, Y.J. Wan, H. Yowonto, J. Li, C.L. Tao, M.D. James, C.L. Tan, G.F. Blackburn, T.J. Maede, J. Am. Chem. Soc. 123, 1111 (2001)

  40. 40.

    T. Ihara, M. Nakayama, M. Murata, K. Nakano, M. Maeda, Chem. Commun. 17, 1609 (1997)

  41. 41.

    C. Biot, L. Delhaes, L.A. Maciejewaski, M. Mortuaire, D. Camus, D. Dive, J.S. Brocard, Eur. J. Med. Chem. 35, 707 (2000)

  42. 42.

    C. Biot, G. Glorian, L.A. Maciejewaski, J.S. Brocard, J. Med. Chem. 40, 3715 (1997)

  43. 43.

    C. Biot, L. Delhaes, M. N’Diaye, L.A. Maciejewaski, D. Camus, D. Dive, J.S. Brocard, Bioorg. Med. Chem. 7, 2843 (1999)

  44. 44.

    B. Cottineau, P. Toto, C. Marot, A. Pipaud, J. Chenault, Bioorg. Med. Chem. Lett. 12, 2105 (2002)

  45. 45.

    H. Yu, L. Shao, J. Fang, J. Organomet. Chem. 692, 991 (2007)

  46. 46.

    M. Zora, M. Görmen, J. Organomet. Chem. 692, 5026 (2007)

  47. 47.

    K.D. Safa, H. Abbasi, R. Teimuri-Mofrad, F.A. Charandabi, Aust. J. Chem. 67, 784 (2014)

  48. 48.

    R. Teimuri-Mofrad, F. Mirzaei, H. Abbasi, K.D. Safa, Comptes Rendus Chim. 20, 197 (2017)

  49. 49.

    R. Teimuri-Mofrad, K.D. Safa, K. Rahimpour, J. Organometal. Chem. 758, 36 (2014)

  50. 50.

    R. Teimuri-Mofrad, H. Abbasi, K.D. Safa, B. Tahmasebi, Arkivoc 4, 371 (2016)

  51. 51.

    R. Teimuri-Mofrad, K. Rahimpour, R. Ghadari, J. Organomet. Chem. 811, 14 (2016)

  52. 52.

    R. Teimuri-Mofrad, K. Rahimpour, R. Ghadari, J. Organomet. Chem. 846, 397 (2017)

  53. 53.

    R. Teimuri-Mofrad, K. Rahimpour, R. Ghadari, S. Ahmadi-Kandjani, J. Mol. Liq. 244, 322 (2017)

  54. 54.

    R. Teimuri-Mofrad, K. Rahimpour, A.R. Vaez, Appl. Organomet. Chem. 32, e4031 (2018)

  55. 55.

    R. Teimuri-Mofrad, K. Rahimpour, A. Poursadegh, Mater. Chem. Phys. 200, 384 (2017)

  56. 56.

    R. Teimuri-Mofrad, A. Shahrisa, M. Gholamhosseini-Nazari, N. Arsalani, Res. Chem. Intermed. 42, 3425 (2016)

  57. 57.

    A. Shahrisa, R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, Mol. Divers. 19, 87 (2015)

  58. 58.

    A. Shahrisa, R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, Synlett 26, 1031 (2015)

  59. 59.

    R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, S. Esmati, A. Shahrisa, Res. Chem. Intermed. 43, 6845 (2017)

  60. 60.

    R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, E. Payami, S. Esmati, Appl. Organomet. Chem. 32, e3955 (2018)

  61. 61.

    R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, S. Esmati, A. Shahrisa, J. Chem. Sci. 129, 1449 (2017)

  62. 62.

    F. Janati, M.M. Heravi, A.M. Shokraie, Synth. React. Inorg. Metal Org. Chem. 45, 1 (2015)

  63. 63.

    Z.P. Zhang, J.M. Wen, J.H. Li, W.X. Hu, J. Chem. Res. 33, 162 (2009)

  64. 64.

    I. Szatmari, F. Fulop, Curr. Org. Chem. 1, 155 (2004)

  65. 65.

    J. Mou, G. Gao, C. Chen, J. Liu, J. Gao, Y. Liu, D. Pei, RSC Adv. 7, 13868 (2017)

  66. 66.

    M. Kidwai, R. Chauhan, Asian. J. Org. Chem. 2, 395 (2013)

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Acknowledgement

We gratefully acknowledge the financial support provided by the Research Council of University of Tabriz.

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Correspondence to Reza Teimuri-Mofrad.

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Teimuri-Mofrad, R., Abbasi, H., Vahedinia, T. et al. Synthesis of Ferrocenyl Based Betti Bases by a Mannich-Type Three-Component Reaction and Investigation of Their Electrochemical Behavior. J Inorg Organomet Polym 30, 955–964 (2020). https://doi.org/10.1007/s10904-019-01258-1

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Keywords

  • Multicomponent reaction
  • Betti bases
  • Ferrocene
  • Piperazine
  • Electrochemical behaviour