Skip to main content

Advertisement

Log in

Expeditious green synthesis of 3,4-disubstituted isoxazole-5(4H)-ones catalyzed by nano-MgO

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this work, it was found that magnesium oxide nanoparticles (nano-MgO) catalyzed one-pot three-component reaction of hydroxylamine hydrochloride with aryl aldehydes (or heteroaryl aldehydes) and β-oxoesters to synthesize some biologically active isoxazole-5(4H)-one-based heterocycles. The reactions were completed using 3 mol% catalyst loading in aqueous medium at room temperature. Nano-MgO was synthesized by precipitation and hydrothermal treatment of aqueous salt solution. The structure of the nano-MgO was characterized by X-ray diffraction (XRD) and scanning electron microscopy (SEM) analyses. The presented environmentally friendly heterocyclization offers some interesting merits, including safety, high product yield, mild conditions, low cost, minimal waste, good atom efficiency, catalyst recoverable, energy efficiency, avoidance of hazardous organic solvents, and easy workup.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 1
Scheme 2
Fig. 6

Similar content being viewed by others

References

  1. W.T. Meng, Y. Zheng, J. Nie, H.Y. Xiong, J.A. Ma, J. Org. Chem. 78, 559 (2013)

    Article  CAS  Google Scholar 

  2. H. Zhang, B. Wang, L. Cui, X. Bao, J. Qu, Y. Song, Eur. J. Org. Chem. 2143 (2015)

  3. G.Q. Li, Y.B. Zhang, H.S. Guan, Fitoterapia 79, 238 (2008)

    Article  CAS  Google Scholar 

  4. T.F. Niu, M.F. Lv, L. Wang, W.B. Yi, C. Cai, Org. Biomol. Chem. 11, 1040 (2013)

    Article  CAS  Google Scholar 

  5. A.P. Kozikowski, S. Tapadar, D.N. Luchini, K.H. Kim, D.D. Billadeau, J. Med. Chem. 51, 4370 (2008)

    Article  CAS  Google Scholar 

  6. A.A. Vieira, F.R. Bryk, G. Conte, A.J. Bortoluzzi, H. Gallardo, Tetrahedron Lett. 50, 905 (2009)

    Article  CAS  Google Scholar 

  7. J. Yong, C. Lu, X. Wu, Med. Chem. Commun. 5, 968 (2014)

    Article  CAS  Google Scholar 

  8. S.K. Laughlin, M.P. Clark, J.F. Djung, A. Golebiowski, T.A. Brugel, M. Sabat, R.G. Bookland, M.J. Laufersweiler, J.C. VanRens, J.A. Townes, B. De, L.C. Hsieh, S.C. Xu, R.L. Walter, M.J. Mekel, M.J. Janusz, Bioorg. Med. Chem. Lett. 15, 2399 (2005)

    Article  CAS  Google Scholar 

  9. A.H. Reshak, S. Azam, Mater. Sci. Semicond. Process. 30, 197 (2015)

    Article  CAS  Google Scholar 

  10. S. Biju, M.L.P. Reddy, A.H. Cowley, K.V. Vasudevan, J. Mater. Chem. 19, 5179 (2009)

    Article  CAS  Google Scholar 

  11. E.S. Darwish, K.A. Atia, A.M. Farag, Heterocycles 89, 1393 (2014)

    Article  CAS  Google Scholar 

  12. A.M. Jawalekar, E. Reubsaet, F.P.J.T. Rutjes, F.L. van Delft, Chem. Commun. 47, 3198 (2011)

    Article  CAS  Google Scholar 

  13. H.L. Liu, Z.F. Geng, S.Y. Zhang, J. Han, Heterocycles 89, 1221 (2014)

    Article  CAS  Google Scholar 

  14. W.S. Hamama, M.E. Ibrahim, H.H. Zoorob, Synth. Commun. 43, 2393 (2013)

    Article  CAS  Google Scholar 

  15. W. Hallenbach, O. Guth, T. Seitz, H.J. Wroblowsky, P. Desbordes, U. Wachendorff-Neumann, P. Dahmen, A. Voerste, P. Lösel, O. Malsam, R. Rama, H. Hadano, 2012, US Patent, Pub. No.: US 2012/0065063A1

  16. W. Hallenbach, O. Guth, T. Seitz,, H.J. Wroblowsy, P. Desbords, U. Wachendorff, P. Dahmen, A. Voerste, P. Losel, O. Malsam, R. Rama, H. Hadano, 2011, WIPO Patent Application WO/2011/161035A1

  17. J.P. Demers, W.E. Hageman, S.G. Johnson, D.H. Klaubert, R.A. Look, J.B. Moore, Bioorg. Med. Chem. Lett. 4, 2451 (1994)

    Article  CAS  Google Scholar 

  18. T. Ishioka, A. Tanatani, K. Nagasawa, Y. Hashimoto, Bioorg. Med. Chem. Lett. 13, 2655 (2003)

    Article  CAS  Google Scholar 

  19. T. Ishioka, A. Kubo, Y. Koiso, K. Nagasawa, A. Itai, Y. Hashimoto, Bioorg. Med. Chem. 10, 1555 (2002)

    Article  CAS  Google Scholar 

  20. B. Kafle, N.G. Aher, D. Khadka, H. Park, H. Cho, Chem. Asian J. 6, 2073 (2011)

    Article  CAS  Google Scholar 

  21. N. Panathur, N. Gokhale, U. Dalimba, P.V. Koushik, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett. 25, 2768 (2015)

    Article  CAS  Google Scholar 

  22. X.H. Zhang, L.Y. Wang, Y.H. Zhan, Y.L. Fu, G.H. Zhai, Z.Y. Wen, J. Mol. Struct. 994, 371 (2011)

    Article  CAS  Google Scholar 

  23. X.H. Zhang, Y.H. Zhan, D. Chen, D. Chen, F. Wang, L.Y. Wang, Dyes Pigments 93, 1408 (2012)

    Article  CAS  Google Scholar 

  24. F. Wang, A.W. Harper, M.S. Lee, L.R. Dalton, Chem. Mater. 11, 2285 (1999)

    Article  CAS  Google Scholar 

  25. S. Alıas, R. Andreu, M.J. Blesa, M.A. Cerdan, S. Franco, J. Garın, C. Lopez, J. Orduna, J. Sanz, R. Alicante, B. Villacampa, M. Allain, J. Org. Chem. 73, 5890 (2008)

    Article  Google Scholar 

  26. D. Jiang, Z. Xue, Y. Li, H. Liu, W. Yang, J. Mater. Chem. 1, 5694 (2013)

    Article  CAS  Google Scholar 

  27. P.V. Bedworth, Y. Cai, A. Jen, S.R. Marder, J. Org. Chem. 61, 2242 (1996)

    Article  CAS  Google Scholar 

  28. S. Biju, M.L.P. Reddy, R.O. Freire, Inorg. Chem. Commun. 10, 393 (2007)

    Article  CAS  Google Scholar 

  29. E. Aret, H. Meekes, E. Vlieg, G. Deroover, Dyes Pigments 72, 339 (2007)

    Article  CAS  Google Scholar 

  30. M.R.N. Capreti, I.D. Jurberg, Org. Lett. 17, 2490 (2015)

    Article  CAS  Google Scholar 

  31. J.S. Wzorek, T.F. Knopfel, I. Sapountzis, D.A. Evans, Org. Lett. 14, 5840 (2012)

    Article  CAS  Google Scholar 

  32. C.O. Kappe, D. Kvaskoff, D.W.J. Moloney, R. Flammang, C. Wentrup, J. Org. Chem. 66, 1827 (2001)

    Article  CAS  Google Scholar 

  33. T.M. Kaiser, J.H. Huang, J. Yang, J. Org. Chem. 78, 6297 (2013)

    Article  CAS  Google Scholar 

  34. I. Dias-Jurberg, F. Gagosz, S.Z. Zard, Org. Lett. 12, 416 (2010)

    Article  CAS  Google Scholar 

  35. G. Sabitha, M.M. Reddy, B. Archana, J.S. Yadav, Synth. Commun. 28, 573 (1998)

    Article  CAS  Google Scholar 

  36. B.D. Cui, S.W. Li, J. Zuo, Z.J. Wu, X.M. Zhang, W.C. Yuan, Tetrahedron 70, 1895 (2014)

    Article  CAS  Google Scholar 

  37. C. Wentrup, M. Wiedenstritt, H.W. Winter, Aust. J. Chem. 68, 1233 (2015)

    CAS  Google Scholar 

  38. C. Wentrup, H.W. Winter, Angew. Chem. Int. Ed. Engl. 17, 609 (1978)

    Article  Google Scholar 

  39. C. Wentrup, J. Becker, H.W. Winter, Angew. Chem. Int. Ed. 54, 5702 (2015)

    Article  CAS  Google Scholar 

  40. G.I. Yranzo, J. Elguero, R. Flammang, C. Wentrup, Eur. J. Org. Chem. 2001, 2209 (2001)

    Article  Google Scholar 

  41. I. Nakamura, M. Okamoto, M. Terada, Org. Lett. 12, 2453 (2010)

    Article  CAS  Google Scholar 

  42. M. Cocivera, A. Emo, H.E. Chen, S. Vaish, J. Am. Chem. Soc. 98, 7362 (1976)

    Article  CAS  Google Scholar 

  43. D. Villemin, B. Martin, B. Garrigues, Synth. Commun. 23, 2251 (1993)

    Article  CAS  Google Scholar 

  44. G. Brancatelli, G. Bruno, F. Nicolo, M. Cordaro, G. Grassi, F. Risitano, A. Scala, J. Mol. Struct. 998, 157 (2011)

    Article  CAS  Google Scholar 

  45. J.J. Donleawy, E.E. Gilbert, J. Am. Chem. Soc. 59, 1072 (1937)

    Article  Google Scholar 

  46. D.B. Lowe, S. Magnuson, N. Qi, A.M. Campbell, J. Cook, Z. Hong, M. Wang, M. Rodriguez, F. Achebe, H. Kluender, W.C. Wong, W.H. Bullock, A.I. Salhanick, T. Witman-Jones, M.E. Bowling, C. Keiper, K.B. Clairmont, Bioorg. Med. Chem. Lett. 14, 3155 (2004)

    Article  CAS  Google Scholar 

  47. A.P. Chavan, A.B. Pinjari, P.C. Mhaske, J. Heterocycl. Chem. 52, 1911 (2015)

    Article  CAS  Google Scholar 

  48. Q. Liu, R.T. Wu, J. Chem. Res. 35, 598 (2011)

    Article  CAS  Google Scholar 

  49. Q. Liu, Y.N. Zhang, Bull. Korean Chem. Soc. 32, 3559 (2011)

    Article  CAS  Google Scholar 

  50. Y.Q. Zhang, J.J. Ma, C. Wang, J.C. Li, D.N. Zhang, X.H. Zang, J. Li, Chin. J. Org. Chem. 28, 141 (2008)

    Google Scholar 

  51. K. Ablajan, H. Xiamuxi, Chin. Chem. Lett. 22, 151 (2011)

    Article  CAS  Google Scholar 

  52. M. Mirzazadeh, G.H. Mahdavinia, Eur. J. Chem. 9, 425 (2012)

    CAS  Google Scholar 

  53. S.N. Maddila, S. Maddila, W.E. Zyl, S.B. Jonnalagadda, Res. Chem. Intermed. (2015). doi:10.1007/s11164-015-2167-2

    Google Scholar 

  54. H. Kiyani, F. Ghorbani, Heterocycl. Lett. 3, 359 (2013)

    CAS  Google Scholar 

  55. H. Kiyani, F. Ghorbani, Elixir Org. Chem. 58, 14948 (2013)

    Google Scholar 

  56. H. Kiyani, F. Ghorbani, Org. Chem. Indian J. 13, 97 (2013)

    Google Scholar 

  57. H. Kiyani, F. Ghorbani, Open J. Org. Chem. 1, 5 (2013)

    Google Scholar 

  58. Q. Liu, X. Hou, Phosphorus Sulfur Silicon Relat. Elem. 187, 448 (2012)

    Article  CAS  Google Scholar 

  59. M.G. Dekamin, S.Z. Peyman, Monatsh. Chem. (2015). doi:10.1007/s00706-015-1565-x

    Google Scholar 

  60. H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 41, 2653 (2015)

    Article  CAS  Google Scholar 

  61. H. Kiyani, F. Ghorbani, Heterocycl. Lett. 3, 145 (2013)

    CAS  Google Scholar 

  62. H. Kiyani, F. Ghorbani, J. Saudi Chem. Soc. (2013). doi:10.1016/j.jscs.2013.11.002

    Google Scholar 

  63. H. Kiyani, M. Jabbari, A. Mosallanezhad, Jordan J. Chem. 9, 279 (2014)

    Article  Google Scholar 

  64. H. Kiyani, A. Kanaani, D. Ajloo, F. Ghorbani, M. Vakili, Res. Chem. Intermed. 41, 7739 (2015)

    Article  CAS  Google Scholar 

  65. H. Kiyani, H. Darbandi, A. Mosallanezhad, F. Ghorbani, Res. Chem. Intermed. 41, 7561 (2015)

    Article  CAS  Google Scholar 

  66. H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 41, 7847 (2015)

    Article  CAS  Google Scholar 

  67. D. Setamdideh, J. Mex. Chem. Soc. 59, 191 (2015)

    Google Scholar 

  68. A.U. Khandebharad, S.R. Sarda, C.H. Gill, B.R. Agrawal, Res. J. Chem. Sci. 5, 27 (2015)

    CAS  Google Scholar 

  69. F. Saikh, J. Das, S. Ghosh, Tetrahedron Lett. 54, 4679 (2013)

    Article  CAS  Google Scholar 

  70. Y.Q. Zhang, C. Wang, M.Y. Zhang, P.L. Cui, Y.M. Li, X. Zhou, J.C. Li, Chin. J. Org. Chem. 28, 914 (2008)

    CAS  Google Scholar 

  71. K. Ablajan, H. Xiamuxi, Synth. Commun. 42, 1128 (2012)

    Article  CAS  Google Scholar 

  72. Q.F. Cheng, X.Y. Liu, Q.F. Wang, L.S. Liu, W.J. Liu, Q. Lin, X.J. Yang, Chin. J. Org. Chem. 29, 1267 (2009)

    CAS  Google Scholar 

  73. S. Tu, J. Zhang, R. Jia, B. Jiang, Y. Zhang, H. Jiang, Org. Biomol. Chem. 5, 1450 (2007)

    Article  CAS  Google Scholar 

  74. B.M. Choudary, K.V.S. Ranganath, U. Pal, M.L. Kantam, B.J. Sreedhar, J. Am. Chem. Soc. 127, 13167 (2005)

    Article  CAS  Google Scholar 

  75. V.R. Chintareddy, M.L. Kantam, Catal. Surv. Asia 15, 89 (2011)

    Article  CAS  Google Scholar 

  76. B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 5004 (2012)

    Article  CAS  Google Scholar 

  77. G. Brahmachari, S. Laskar, Phosphorus Sulfur Silicon Relat. Elem. 189, 873 (2014)

    Article  CAS  Google Scholar 

  78. C. Xu, J.K. Bartley, D.I. Enache, D.W. Knight, G.J. Hutchings, Synthesis 3468 (2005)

  79. M. Abaszadeh, M. Seifi, A. Asadipour, Synth. React. Inorg. Met. Org. Chem. 46, 512 (2016)

    Article  CAS  Google Scholar 

  80. H. Sheibani, M. Seifi, A. Bazgir, Synth. Commun. 39, 1055 (2009)

    Article  CAS  Google Scholar 

  81. L. Chakrapani, M.L. Kantam, Synth. Commun. 41, 3442 (2011)

    Article  CAS  Google Scholar 

  82. V.K. Das, A.J. Thakur, Tetraderon Lett. 54, 4164 (2013)

    Article  CAS  Google Scholar 

  83. J. Safaei-Ghomi, F. Eshteghal, M.A. Ghasemzadeh, Acta Chim. Slov. 61, 703 (2014)

    CAS  Google Scholar 

  84. M. Tajbakhsh, M. Farhang, A.S. Hosseini, J. Iran. Chem. Soc. 11, 665 (2014)

    Article  CAS  Google Scholar 

  85. N. Shariati, R.J. Baharfar, Chin. Chem. Soc. 61, 337 (2014)

    Article  CAS  Google Scholar 

  86. H. Naeimi, K. Rabiei, M. Rezaei, F. Meshkani, J. Iran. Chem. Soc. 10, 161 (2013)

    Article  CAS  Google Scholar 

  87. H. Naeimi, N. Alishahi, J. Exp. Nanosci. 10, 222 (2015)

    Article  CAS  Google Scholar 

  88. H. Mirzaie, A. Davoodnia, Chin. J. Catal. 33, 1502 (2012)

    Article  Google Scholar 

  89. Z. Zarnegar, J. Safari, J. Exp. Nanosci. 10, 651 (2015)

    Article  CAS  Google Scholar 

  90. V.K. Das, R.R. Devi, A. Thakur, J. Appl. Catal. A Gen. 456, 118 (2013)

    Article  CAS  Google Scholar 

  91. J. Safari, Z. Zarnegar, M. Heydarian, J. Taibah Univ. Sci. 7, 17 (2013)

    Article  Google Scholar 

  92. H. Naeimi, Z. Rashid, A.H. Zarnani, R. Ghahremanzadeh, J. Nanopart. Res. 16, 2416 (2014)

    Article  Google Scholar 

  93. F. Shirini, M. Abedini, J. Nanosci. Nanotechnol. 13, 4838 (2013)

    Article  CAS  Google Scholar 

  94. D. Kumar, V.B. Reddy, B.G. Mishra, R.K. Rana, M.N. Nadagouda, R.S. Varma, Tetrahedron 63, 3093 (2007)

    Article  CAS  Google Scholar 

  95. S.H.S. Azzam, G.T. Chandrappa, M.A. Pasha, Lett. Org. Chem. 10, 283 (2013)

    Article  CAS  Google Scholar 

  96. A. Mossafaii Rad, M. Mokhtary, Int. Nano Lett. 5, 109 (2015)

    Article  Google Scholar 

  97. M. Hosseini-Sarvari, G. Parhizgar, Green Chem. Lett. Rev. 5, 439 (2012)

    Article  CAS  Google Scholar 

  98. R. Baharfar, N. Shariati, C. R. Chimie 17, 413 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Damghan University is acknowledged for provision of facilities and materials.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hamzeh Kiyani.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kiyani, H., Ghorbani, F. Expeditious green synthesis of 3,4-disubstituted isoxazole-5(4H)-ones catalyzed by nano-MgO. Res Chem Intermed 42, 6831–6844 (2016). https://doi.org/10.1007/s11164-016-2498-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2498-7

Keywords

Navigation