Advertisement

Efficient synthesis of α-aminonitriles over homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles (MSNs-HPZ-SO3H), as a reusable acid catalyst

  • Zahra Nasresfahani
  • Mohamad Z. KassaeeEmail author
  • Esmaiel Eidi
Original Paper
  • 7 Downloads

Abstract

Good to excellent yields of α-aminonitriles are achieved through three-component Strecker reaction of aldehydes or ketones with amines and trimethylsilyl cyanides over homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles (MSNs-HPZ-SO3H). The advantages of this protocol include: simplicity, short reaction time, high yields, ease of product isolation and reusability of the catalyst.

Graphical abstract

MSNs-HPZ-SO3H is prepared as an acid catalyst and successfully used for three-component Strecker reaction of aldehydes or ketones with amines and trimethylsilyl cyanides (TMSCN) under solvent-free conditions, a straightforward strategy for the synthesis of α-aminonitriles.

Keywords

α-Aminonitriles Homopiperazine Mesoporous silica Nanocatalyst One-pot synthesis 

Notes

Compliance with ethical standards

Conflict of interest

The authors declare that there is no conflict of interest.

Supplementary material

13738_2019_1654_MOESM1_ESM.docx (1.7 mb)
Supplementary material 1 (DOCX 1730 kb)

References

  1. 1.
    L. Banfi, G. Guanti, R. Riva, Chem. Commun. 11, 985 (2000)CrossRefGoogle Scholar
  2. 2.
    W.L. Matier, D.A. Owens, W.T. Comer, D. Deitchman, H.C. Ferguson, R.J. Seidehamel, J.R. Young, J. Med. Chem. 16, 901 (1973)CrossRefGoogle Scholar
  3. 3.
    J. Marco, S.T. Ingate, P. Manzano, Tetrahedron Lett. 39, 4123 (1998)CrossRefGoogle Scholar
  4. 4.
    S. Velázquez, C. Chamorro, M.-J. Pérez-Pérez, R. Alvarez, M.-L. Jimeno, A. Martín-Domenech, C. Pérez, F. Gago, E. De Clercq, J. Balzarini, J. Med. Chem. 41, 4636 (1998)CrossRefGoogle Scholar
  5. 5.
    D. Enders, J.P. Shilvock, Chem. Soc. Rev. 29, 359 (2000)CrossRefGoogle Scholar
  6. 6.
    R.O. Duthaler, Tetrahedron 50, 1539 (1994)CrossRefGoogle Scholar
  7. 7.
    S.J. Zuend, M.P. Coughlin, M.P. Lalonde, E.N. Jacobsen, Nature 461, 968 (2009)CrossRefGoogle Scholar
  8. 8.
    L.M. Weinstock, P. Davis, B. Handelsman, R.J. Tull, J. Org. Chem. 32, 2823 (1967)CrossRefGoogle Scholar
  9. 9.
    A. Strecker, Liebigs Ann. Chem. 75, 27 (1850)CrossRefGoogle Scholar
  10. 10.
    B.A.B. Prasad, A. Bisai, V.K. Singh, Tetrahedron Lett. 45, 9565 (2004)CrossRefGoogle Scholar
  11. 11.
    S.K. De, R.A. Gibbs, J. Mol. Catal. A: Chem. 232, 123 (2005)CrossRefGoogle Scholar
  12. 12.
    S. Kobayashi, T. Busujima, Chem. Commun. 9, 981 (1998)CrossRefGoogle Scholar
  13. 13.
    S.K. De, J. Mol. Catal. A: Chem. 225, 169 (2005)CrossRefGoogle Scholar
  14. 14.
    Z.-L. Shen, S.-J. Ji, T.-P. Loh, Tetrahedron 64, 8159 (2008)CrossRefGoogle Scholar
  15. 15.
    A. Majhi, S.S. Kim, S.T. Kadam, Tetrahedron 64, 5509 (2008)CrossRefGoogle Scholar
  16. 16.
    M. Narasimhulu, T.S. Reddy, K.C. Mahesh, S.M. Reddy, A.V. Reddy, Y. Venkateswarlu, J. Mol. Catal. A: Chem. 264, 288 (2007)CrossRefGoogle Scholar
  17. 17.
    B. Karimi, A.A. Safari, J. Organomet. Chem. 693, 2967 (2008)CrossRefGoogle Scholar
  18. 18.
    B.M. Reddy, B. Thirupathi, M.K. Patil, J. Mol. Catal. A: Chem. 307, 154 (2009)CrossRefGoogle Scholar
  19. 19.
    J.S. Yadav, B.V.S. Reddy, B. Eshwaraiah, M. Srinivas, P. Vishnumurthy, New J. Chem. 27, 462 (2003)CrossRefGoogle Scholar
  20. 20.
    M.Z. Kassaee, H. Masrouri, F. Movahedi, Appl. Catal. A Gen. 395, 28 (2011)CrossRefGoogle Scholar
  21. 21.
    S. Baghery, M.A. Zolfigol, R. Schirhagl, M. Hasani, M.C.A. Stuart, A. Nagl, Appl. Organomet. Chem. 31, e3883 (2017)CrossRefGoogle Scholar
  22. 22.
    B. Karimi, D. Zareyee, J. Mater. Chem. 19, 8665 (2009)CrossRefGoogle Scholar
  23. 23.
    J. Jarusiewicz, Y. Choe, K.S. Yoo, C.P. Park, K.W. Jung, J. Org. Chem. 74, 2873 (2009)CrossRefGoogle Scholar
  24. 24.
    K. Iwanami, H. Seo, J.-C. Choi, T. Sakakura, H. Yasuda, Tetrahedron 66, 1898 (2010)CrossRefGoogle Scholar
  25. 25.
    A. Heydari, A. Arefi, S. Khaksar, R.K. Shiroodi, J. Mol. Catal. A: Chem. 271, 142 (2007)CrossRefGoogle Scholar
  26. 26.
    B. Karmakar, J. Banerji, Tetrahedron Lett. 51, 2748 (2010)CrossRefGoogle Scholar
  27. 27.
    M.G. Dekamin, M. Azimoshan, L. Ramezani, Green Chem. 15, 811 (2013)CrossRefGoogle Scholar
  28. 28.
    K. Surendra, N.S. Krishnaveni, A. Mahesh, K.R. Rao, J. Org. Chem. 71, 2532 (2006)CrossRefGoogle Scholar
  29. 29.
    J. Wang, Y. Masui, M. Onaka, Eur. J. Org. Chem. 2010, 1763 (2010)CrossRefGoogle Scholar
  30. 30.
    F. Rajabi, S. Nourian, S. Ghiassian, A.M. Balu, M.R. Saidi, J.C. Serrano-Ruiz, R. Luque, Green Chem. 13, 3282 (2011)CrossRefGoogle Scholar
  31. 31.
    M. Shekouhy, Catal. Sci. Technol. 2, 1010 (2012)CrossRefGoogle Scholar
  32. 32.
    S. Baghery, M.A. Zolfigol, M. Safaiee, D.A. Alonso, A. Khoshnood, Appl. Organomet. Chem. 31, e3775 (2017)CrossRefGoogle Scholar
  33. 33.
    J.S. Yadav, B.V.S. Reddy, B. Eeshwaraiah, M. Srinivas, Tetrahedron 60, 1767 (2004)CrossRefGoogle Scholar
  34. 34.
    A. Dutta, J. Mondal, A.K. Patra, A. Bhaumik, Chem. Eur. J. 18, 13372 (2012)CrossRefGoogle Scholar
  35. 35.
    K. Ghosh, R.A. Molla, M.A. Iqubal, S.M. Islam, Green Chem. 17, 3540 (2015)CrossRefGoogle Scholar
  36. 36.
    M. Hajjami, F. Ghorbani, F. Bakhti, Appl. Catal. A Gen. 470, 303 (2014)CrossRefGoogle Scholar
  37. 37.
    Z. Nasresfahani, M.Z. Kassaee, E. Eidi, New J. Chem. 40, 4720 (2016)CrossRefGoogle Scholar
  38. 38.
    I.I. Slowing, B.G. Trewyn, V.S.-Y. Lin, J. Am. Chem. Soc. 129, 8845 (2007)CrossRefGoogle Scholar
  39. 39.
    H. Ghafuri, A. Rashidizadeh, B. Ghorbani, M. Talebi, New J. Chem. 39, 4821 (2015)CrossRefGoogle Scholar
  40. 40.
    H. Singh, J.K. Rajput, P. Arora, RSC Adv. 6, 84658 (2016)CrossRefGoogle Scholar
  41. 41.
    B.C. Ranu, S.S. Dey, A. Hajra, Tetrahedron 58, 2529 (2002)CrossRefGoogle Scholar
  42. 42.
    G.K.S. Prakash, E. Thomas, I. Bychinskaya, A.G. Prakash, C. Panja, G.A. Olah, Green Chem. 10, 1105 (2008)CrossRefGoogle Scholar
  43. 43.
    J.G. Hernández, M. Turberg, I. Schiffers, C. Bolm, Chem. Eur. J. 22, 14513 (2016)CrossRefGoogle Scholar
  44. 44.
    A. Mobaraki, B. Movassagh, B. Karimi, ACS Comb. Sci. 16, 352 (2014)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  • Zahra Nasresfahani
    • 1
  • Mohamad Z. Kassaee
    • 1
    • 2
    Email author
  • Esmaiel Eidi
    • 1
  1. 1.Department of ChemistryTarbiat Modares UniversityTehranIran
  2. 2.Chemical and Biomolecular EngineeringVanderbilt UniversityNashvilleUSA

Personalised recommendations