Journal of the Iranian Chemical Society

, Volume 11, Issue 3, pp 665–672 | Cite as

MgO nanoparticles as an efficient and reusable catalyst for aza-Michael reaction

  • Mahmood Tajbakhsh
  • Maryam Farhang
  • Ali Asghar Hosseini
Original Paper
First Online:
Received:
Accepted:

Abstract

MgO nanoparticles were prepared by an improved sol–gel technique which appeared to have narrow size distributions. The synthesized magnesium oxide nanoparticles were used as an efficient catalyst in aza-Michael reaction for addition of amines to a series of α,β-unsaturated carbonyl compounds and nitro olefins under solvent-free conditions at room temperature to afford high yields of the β-amino carbonyl and β-nitro amines. The catalyst can be recovered and reused at least five successive runs without loss of activity.

Graphical abstract

Keywords

MgO nanoparticles Conjugate addition Aza-Michael α,β-Unsaturated compounds Solvent free 
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Notes

Acknowledgments

We are thankful to Mazandaran University Research Council for partial support of this work.

References

  1. 1.
    R. Bloch, Chem. Rev. 98, 1407–1438 (1998)CrossRefGoogle Scholar
  2. 2.
    S. Kobayashi, H. Ishitani, Chem. Rev. 99, 1069–1094 (1999)CrossRefGoogle Scholar
  3. 3.
    A. Acc, Cordova. Chem. Res. 37, 102–112 (2004)CrossRefGoogle Scholar
  4. 4.
    E. M-López, P. Merino, T. Tejero, R.P. Herrera, Eur. J. Org. Chem. 2009 , 2401–2420 (2009)CrossRefGoogle Scholar
  5. 5.
    E. Foresti, G. Palmieri, M. Petrini, R. Profeta, Org. Biomol. Chem. 1, 4275–4281 (2003)CrossRefGoogle Scholar
  6. 6.
    M. Liu, M.P. Sibi, Tetrahedron 58, 7991–8035 (2002)CrossRefGoogle Scholar
  7. 7.
    G. Nagendra, C. Madhu, T.M. Vishwanatha, V.V. Sureshbabu, Tetrahedron Lett. 53, 5059–5063 (2012)CrossRefGoogle Scholar
  8. 8.
    S. Comesse, M. Sanselme, A. Daïch, J. Org. Chem. 73, 5566–5569 (2008)CrossRefGoogle Scholar
  9. 9.
    K. Damera, K.L. Reddy, G.V.M. Sharma, Lett. Org. Chem. 6, 151–155 (2009)CrossRefGoogle Scholar
  10. 10.
    B. Weiner, W. SzymaĚski, D.B. Janssen, A.J. Minnaarda, B.L. Feringa, Chem. Soc. Rev. 39, 1656–1691 (2010)CrossRefGoogle Scholar
  11. 11.
    L. Elkaim, L. Grimaud, N.K. Jana, F. Mettetal, C. Tirla, Tetrahedron Lett. 43, 8925–8927 (2002)CrossRefGoogle Scholar
  12. 12.
    C. Palomo, M. Oiarbide, A. Landa, M.C. G-Rego, J.M. García, A. González, J.M. Odriozola, M. M-Pastor, A. Linden, J. Am. Chem. Soc. 124, 8637–8643 (2002)CrossRefGoogle Scholar
  13. 13.
    J.J. Denton, R.J. Turner, W.B. Neier, V.A. Lawon, H.P. Scliedl, J. Am. Chem. Soc. 71, 2048–2050 (1949)CrossRefGoogle Scholar
  14. 14.
    F. Felluga, G. Pitacco, E. Valentin, C.D. Venneri, Tetrahedron:Asymmetry 19, 945–955 (2008)CrossRefGoogle Scholar
  15. 15.
    J.G. Baker, S.J. Hill, R.J. Summers, Trends Pharmacol. Sci. 32, 227–234 (2011)CrossRefGoogle Scholar
  16. 16.
    W.L. Nobles, B.B. Thompson, J. Pharm. Sci. 68, 1554–1555 (1964)CrossRefGoogle Scholar
  17. 17.
    C. Palomo, M. Oiarbide, A. Laso, R. Lo’pez, J. Am. Chem. Soc. 127, 17622–17623 (2005)CrossRefGoogle Scholar
  18. 18.
    X.C. Wang, L.J. Zhang, Z. Zhang, Z.J. Quan, Chinese Chem. Lett. 23, 423–426 (2012)CrossRefGoogle Scholar
  19. 19.
    J.C. Anderson, P. Gareth, G.P. Howell, M. Ron, R.M. Lawrence, C.S. Wilson, J. Org. Chem. 70, 5665–5670 (2005)CrossRefGoogle Scholar
  20. 20.
    A.Y. Rulev, Russ. Chem. Rev. 80, 197–218 (2011)CrossRefGoogle Scholar
  21. 21.
    A.V. Narsaiah, Lett. Org. Chem. 4, 462–464 (2007)CrossRefGoogle Scholar
  22. 22.
    R. Varala, M.M. Alam, S.R. Adapa, Synlett 5, 720–722 (2003)Google Scholar
  23. 23.
    I. Reboule, R. Gil, J. Collin, Tetrahedron Lett. 46, 7761–7764 (2005)CrossRefGoogle Scholar
  24. 24.
    M.J. Bhanushali, N.S. Nandurkar, S.R. Jagtap, B.M. Bhanage, Catal. Commun. 9, 1189–1195 (2008)CrossRefGoogle Scholar
  25. 25.
    S.A. Fernandes, R. Natalino, P.A.R. Gazolla, M.J.D. Silva, G.N. Jham, Tetrahedron Lett. 53, 1630–1633 (2012)CrossRefGoogle Scholar
  26. 26.
    S. Azad, T. Kobayashi, K. Nakano, Y. Ichikawa, H. Kotsuki, Tetrahedron Lett. 50, 48–50 (2009)CrossRefGoogle Scholar
  27. 27.
    X.J. Tang, Z.L. Yan, W.L. Chen, Y.R. Gao, S. Mao, Y.L. Zhang, Y.Q. Wang, Tetrahedron Lett. 54, 2669–2673 (2013)CrossRefGoogle Scholar
  28. 28.
    N. Morimoto, Y. Takeuchi, Y. Nishina, J. Mol. Catal. A: Chem 368, 31–37 (2013)CrossRefGoogle Scholar
  29. 29.
    A.K. Verma, P. Attri, V. Chopra, R.K. Tiwari, R. Chandra, Monatsh. Chem. 139, 1041–1047 (2008)CrossRefGoogle Scholar
  30. 30.
    A.G. Ying, L. Liu, G.F. Wu, G. Chen, X.Z. Chen, W.D. Ye, Tetrahedron Lett. 50, 1653–1657 (2009)CrossRefGoogle Scholar
  31. 31.
    S.R. Roy, A.K. Chakraborti, Org. Lett. 12, 3866–3869 (2010)CrossRefGoogle Scholar
  32. 32.
    X. Chen, X. Li, H. Song, Y. Qian, F. Wang, Tetrahedron Lett. 52, 3588–3591 (2011)CrossRefGoogle Scholar
  33. 33.
    K. Surendra, N.S. Krishnaveni, R. Sridhar, K.R. Rao, Tetrahedron Lett. 47, 2125–2127 (2006)CrossRefGoogle Scholar
  34. 34.
    H. Firouzabadi, N. Iranpoor, A.A. Jafari, Adv. Synth. Catal. 347, 655–661 (2005)CrossRefGoogle Scholar
  35. 35.
    D. Perdicchia, K.A. Jørgensen, J. Org. Chem. 72, 3565–3568 (2007)CrossRefGoogle Scholar
  36. 36.
    K. De, J. Legros, B. Crousse, D. ele Bonnet-Delpon, J. Org. Chem. 74, 6260–6265 (2009)CrossRefGoogle Scholar
  37. 37.
    C. Mukherjee, A.K. Misra, Lett. Org. Chem. 4, 54–59 (2007)CrossRefGoogle Scholar
  38. 38.
    X. Ai, X. Wang, J.M. Liu, Z.M. Ge, T.M. Cheng, R.T. Li, Tetrahedron 66, 5373–5377 (2010)CrossRefGoogle Scholar
  39. 39.
    A.P. Esteves, M.E. Silva, L.M. Rodrigues, A.M.F. Oliveira-Campos, R. Hrdina, Tetrahedron Lett. 48, 9040–9043 (2007)CrossRefGoogle Scholar
  40. 40.
    L. You, S. Feng, R. An, X. Wang, D. Bai, Tetrahedron Lett. 49, 5147–5150 (2008)CrossRefGoogle Scholar
  41. 41.
    J. Lv, H. Wu, Y. Wang, Eur. J. Org. Chem. 11, 2073–2083 (2010)CrossRefGoogle Scholar
  42. 42.
    K.P. Dhake, P.J. Tambade, R.S. Singhal, B.M. Bhanage, Tetrahedron Lett. 51, 4455–4458 (2010)CrossRefGoogle Scholar
  43. 43.
    L.N. Monsalve, F. Gillanders, A. Baldessari, Eur. J. Org. Chem. 6, 1164–1170 (2012)CrossRefGoogle Scholar
  44. 44.
    G. Imanzadeh, F. Ahmadi, M. Zamanloo, Y. Mansoori, Molecules 15, 7353–7362 (2010)CrossRefGoogle Scholar
  45. 45.
    F. Tamaddon, M. Tayefi, E. Hosseini, E. Zare, J. Mol. Catal. A: Chem. 366, 36–42 (2013)CrossRefGoogle Scholar
  46. 46.
    M.L. Kantam, S. Laha, J. Yadav, S. Jha, Tetrahedron Lett. 50, 4467–4469 (2009)CrossRefGoogle Scholar
  47. 47.
    V.R. Choudhary, D.K. Dumbre, S.K. Patil, RSC Adv. 2, 7061–7065 (2012)CrossRefGoogle Scholar
  48. 48.
    S.L. Xie, Y.H. Hui, X.J. Long, C.C. Wang, Z.F. Xie, Chinese Chem. Lett. 24, 28–30 (2013)CrossRefGoogle Scholar
  49. 49.
    L. Dai, Y. Zhang, Q. Dou, X. Wang, Y. Chen, Tetrahedron 69, 1712–1716 (2013)CrossRefGoogle Scholar
  50. 50.
    L. Li, Z. Liu, Q. Ling, X. Xing, J. Mol. Catal. A: Chem. 353, 178–184 (2012)CrossRefGoogle Scholar
  51. 51.
    L.T.L. Nguyen, T.T. Nguyen, K.D. Nguyen, N.T.S. Phan, Appl. Catal. A 425, 44–52 (2012)CrossRefGoogle Scholar
  52. 52.
    M. Filice, M. Marciello, M.D.P. Morales, J.M. Palomo, Chem. Commun. 49, 6876–6878 (2013)CrossRefGoogle Scholar
  53. 53.
    A. Fihri, M. Bouhrara, B. Nekoueishahraki, J.-M. Basset, V. Polshettiwar, Chem. Soc. Rev. 40, 5181–5203 (2011)CrossRefGoogle Scholar
  54. 54.
    L. Yip, T.M. Kubczyk, T.E. Davies, S.H. Taylor, D.C. Apperley, A.E. Graham, Catal. Sci. Technol. 2, 2258–2263 (2012)CrossRefGoogle Scholar
  55. 55.
    Q. Zhang, H. Su, J. Luo, Y. Wei, Catal. Sci. Technol. 3, 235–243 (2013)CrossRefGoogle Scholar
  56. 56.
    F. Tamaddon, F. Aboee, A. Nasiri, Catal. Commun. 16, 194–197 (2011)CrossRefGoogle Scholar
  57. 57.
    J. Mu, L. Zhang, M. Zhao, Y. Wang, J. Mol. Catal. A: Chem. 378, 30–37 (2013)CrossRefGoogle Scholar
  58. 58.
    M. L. Kantam, S. V. Manorama, P. Basak, V. R. Chintareddy, S. K. Bhargava, in Nanoscale oxides in catalysis: “Manipulation of Nanoscale Materials: An Introduction to Nanoarchitectonics” ed. By K. Ariga (RSC, 2012), p. 129-164Google Scholar
  59. 59.
    V.R. Chintareddy, M.L. Kantam, Catal. Surv. Asia 15, 89–110 (2011)CrossRefGoogle Scholar
  60. 60.
    C.H. Xu, J.K. Bartley, D.I. Enache, D.W. Knight, G.J. Hutchings, Synthesis 19, 3468–3476 (2005)Google Scholar
  61. 61.
    A. Zare, A. Hasaninejad, A. Khalafi-Nezhad, A.R. Moosavi Zare, A. Parhami, Arkivoc 2007, 105–108 (2007)CrossRefGoogle Scholar
  62. 62.
    N. Na, S. Zhang, S. Wang, X. Zhang, J. Am. Chem. Soc. 128, 14420–14421 (2006)CrossRefGoogle Scholar
  63. 63.
    M. Bag, S. Adak, R. Sarkar, Ceram. Int. 38, 2339–2346 (2012)CrossRefGoogle Scholar
  64. 64.
    X.S. Ye, J. Sha, Z.K. Jiao, L.D. Zhang, Nanostruct. Mater. 8, 945–951 (1997)CrossRefGoogle Scholar
  65. 65.
    M. Sterrer, O. Diwald, E. Knozinger, J. Phys. Chem. B 104, 3601–3607 (2000)CrossRefGoogle Scholar
  66. 66.
    M. Babaie, H. Sheibani, Arab. J. Chem. 4, 159–162 (2011)CrossRefGoogle Scholar
  67. 67.
    H. Sheibani, M. Seifi, A. Bazgir, Synth. Commun. 39, 1055–1064 (2009)CrossRefGoogle Scholar
  68. 68.
    M.L. Kantam, K. Mahendar, B. Sreedhar, B.M. Choudary, S.K. Bhargava, S.H. Priver, Tetrahedron 66, 5042–5052 (2010)CrossRefGoogle Scholar
  69. 69.
    B. Karmakar, J. Banerji, Tetrahedron Lett. 52, 4957–4960 (2011)CrossRefGoogle Scholar
  70. 70.
    B. Karmakar, J. Banerji, Tetrahedron Lett. 52, 6584–6586 (2011)CrossRefGoogle Scholar
  71. 71.
    B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 5004–5007 (2012)CrossRefGoogle Scholar
  72. 72.
    M.L. Kantam, K. Mahendar, S. Bhargava, J. Chem. Sci. 122, 63–69 (2010)CrossRefGoogle Scholar
  73. 73.
    M.L. Kantam, K. Mahendar, B. Sreedhar, B.M. Choudary, S.K. Bhargava, S.H. Priver, Tetrahedron 66, 5042–5052 (2010)CrossRefGoogle Scholar
  74. 74.
    B.M. Choudary, M.L. Kantam, K.V.S. Ranganath, K. Mahendar, B. Sreedhar, J. Am. Chem. Soc. 126, 3396–3397 (2004)CrossRefGoogle Scholar
  75. 75.
    B.M. Choudary, K.V.S. Ranganath, U. Pal, M.L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 127, 13167–13171 (2005)CrossRefGoogle Scholar
  76. 76.
    Y. Xi, R.J. Davis, J. Mol. Catal. A: Chem. 341, 22–27 (2011)CrossRefGoogle Scholar
  77. 77.
    L. Chakrapani, M. L-Kantam, Synth. Commun. 41, 3442–3447 (2011)CrossRefGoogle Scholar
  78. 78.
    V.K. Das, A.J. Thakur, Tetrahedron Lett. 54, 4164–4166 (2013)CrossRefGoogle Scholar
  79. 79.
    M.L. Kantam, K. Mahendar, B. Sreedhar, K. Kumar, B.M. Choudary, Synth. Commun. 38, 3919–3936 (2008)CrossRefGoogle Scholar
  80. 80.
    M.B.M. Reddy, S. Ashoka, G.T. Chandrappa, M.A. Pasha, Catal. Lett. 138, 82–87 (2010)CrossRefGoogle Scholar
  81. 81.
    V.K. Das, R.R. Devi, A.J. Thakur, Appl. Catal. A: Gen. 456, 118–125 (2013)CrossRefGoogle Scholar
  82. 82.
    S. Ardizzone, C.L. Bianchi, B. Vercelli, Appl. Surf. Sci. 126, 169–175 (1998)CrossRefGoogle Scholar
  83. 83.
    D. Beruto, R. Botter, A.W. Searcy, J. Am. Ceram. Soc. 70, 155–160 (1987)CrossRefGoogle Scholar
  84. 84.
    Y. Ding, G. Zhang, H. Wu, B. Hai, L. Wang, Y. Qian, Chem. Mater. 13, 435–440 (2001)CrossRefGoogle Scholar
  85. 85.
    O.B. Koper, I. Lagadic, A. Volodin, K. Klabunde, J. Chem. Mater. 9, 2468–2480 (1997)CrossRefGoogle Scholar
  86. 86.
    D. Kumar, V.B. Reddy, B.G. Mishra, R.K. Rana, M.N. Nadagouda, R.S. Varma, Tetrahedron 63, 3093–3097 (2007)CrossRefGoogle Scholar
  87. 87.
    H. Zhang, Y. Zhang, L. Liu, H. Xu, Y. Yang, Synthesis 13, 2129–2136 (2005)CrossRefGoogle Scholar
  88. 88.
    M. Zahouily, B. Mounir, H. Charki, A. Mezdar, B. Bahlaouan, M. Ouammou, Arkivoc 2006, 178–186 (2006)CrossRefGoogle Scholar
  89. 89.
    C.R. Brindaban, S. Sampak, K.G. Sakar, Tetrahedron 58, 983–988 (2002)CrossRefGoogle Scholar
  90. 90.
    C. Mukherjee, A.K. Misra, Lett. Org. Chem. 4, 54–59 (2007)CrossRefGoogle Scholar
  91. 91.
    J.S. Yadav, A.R. Reddy, Y.G. Rao, A.V. Narsaiah, B.V.S. Reddy, Synthesis 22, 3447–3450 (2007)CrossRefGoogle Scholar
  92. 92.
    G. Choudhary, R.K. Peddinti, Green Chem. 13, 276–282 (2011)CrossRefGoogle Scholar
  93. 93.
    R. Qiu, X. Xu, L. Peng, Y. Zhao, N. Li, S. Yin, Chem. Eur. J. 18, 6172–6182 (2012)CrossRefGoogle Scholar
  94. 94.
    L. Yang, L.W. Xu, W. Zhou, L. Li, C. Gu-Xia, Tetrahedron Lett. 47, 7723–7726 (2006)CrossRefGoogle Scholar
  95. 95.
    A. Ying, M. Zheng, H. Xu, F. Qiu, C. Ge, Res. Chem. Intermed. 37, 883–890 (2011)CrossRefGoogle Scholar
  96. 96.
    A. Ying, Q. Zhang, H. Li, W. Gong, M. He, Res. Chem. Intermed. 39, 517–525 (2013)CrossRefGoogle Scholar
  97. 97.
    Z. Shobeiri, M. Pourayoubi, A. Heydari, T.M. Percino, M.A.L. Ramırez, C. R. Chimie 14, 597–603 (2011)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2013

Authors and Affiliations

  • Mahmood Tajbakhsh
    • 1
  • Maryam Farhang
    • 1
  • Ali Asghar Hosseini
    • 2
  1. 1.Faculty of ChemistryUniversity of MazandaranBabolsarIran
  2. 2.Nanotecnology Laboratory, Department of PhysicsUniversity of MazandaranBabolsarIran

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