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Research on Chemical Intermediates

, Volume 42, Issue 3, pp 2553–2566 | Cite as

Ag/SiO2 as a recyclable catalyst for the facile green synthesis of 3-methyl-4-(phenyl)methylene-isoxazole-5(4H)-ones

  • Surya Narayana Maddila
  • Suresh Maddila
  • Werner E. van Zyl
  • Sreekantha B. JonnalagaddaEmail author
Article

Abstract

An efficient and facile green method for synthesis of 3-methyl-4-(phenyl)methylene-isoxazole-5(4H)-one (4a-m) via room temperature reaction of hydroxylamine, ethylacetoacetate and substituted aromatic aldehydes is designed, using Ag/SiO2 as catalyst with water as solvent. This protocol offers several advantages, such as it being a benign, energy conserving and eco-friendly reaction with products obtained in excellent yields (88–93 %). The reaction requires relatively short reaction times (< 1 h), a simple workup procedure with good atom efficiency and easily recoverable catalyst. The heterogeneous catalyst, Ag/SiO2, was fully characterized and is reusable without loss of activity for up to seven cycles with marginal activity loss.

Graphical Abstract

Keywords

Green synthesis Heterogeneous catalyst Isoxazoles Ag/SiO2 One-pot reaction 

Notes

Acknowledgments

The authors are thankful to the National Research Foundation (NRF) of South Africa, and University of KwaZulu-Natal, Durban, for financial support and research facilities.

Supplementary material

11164_2015_2167_MOESM1_ESM.doc (2.9 mb)
Supplementary material 1 (DOC 3015 kb)

References

  1. 1.
    M.M. Gawande, V.D.B. Bonifacio, R. Luque, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42(12), 5522 (2013)CrossRefGoogle Scholar
  2. 2.
    A.P. Abbott, D. Boothby, G. Capper, D.L. Davies, R.K. Rasheed, J. Am. Chem. Soc. 126, 9142 (2004)CrossRefGoogle Scholar
  3. 3.
    A. Domling, Chem. Rev. 106, 17 (2006)CrossRefGoogle Scholar
  4. 4.
    A. Domling, W. Wang, K. Wang, Chem. Rev. 112(6), 3038 (2012)CrossRefGoogle Scholar
  5. 5.
    S. Maddila, S. Rana, R. Pagadala, S. Kankala, S.N. Maddila, S.B. Jonnalagadda, Catal. Commun. 61, 26 (2015)CrossRefGoogle Scholar
  6. 6.
    Y. Gu, Green Chem. 14, 2091 (2012)CrossRefGoogle Scholar
  7. 7.
    K. Alfonsi, J. Colberg, P.J. Dunn, T. Fevig, S. Jennings, T.A. Johnson, H.P. Kleine, C. Knight, M.A. Nagy, D.A. Perry, M. Stefaniak, Green Chem. 10, 31 (2008)CrossRefGoogle Scholar
  8. 8.
    J.P. Wan, S.F. Gan, G.L. Sun, Y.J.J. Pan, Org. Chem. 74, 2862 (2009)CrossRefGoogle Scholar
  9. 9.
    A. Das, A. Kulkarni, B. Torok, Green Chem. 14, 17 (2012)CrossRefGoogle Scholar
  10. 10.
    J. Virkutyte, R.S. Varma, Green synthesis of nanomaterials: environmental aspects, sustainable nanotechnology and the environment: advances and achievements, Chapter 2, ACS Symposium Series. vol. 1142, p. 11 (2013)Google Scholar
  11. 11.
    M. Choi, F. Kleitz, D. Liu, E.Y. Lee, A. Wha-Seung, R. Ryoo, J. Am. Chem. Soc. 127, 1924 (2005)CrossRefGoogle Scholar
  12. 12.
    P. Bhaumik, T. Kane, P.L. Dhepe, Catal. Sci. Technol. 4, 2904 (2014)CrossRefGoogle Scholar
  13. 13.
    A. Walcarius, Chem. Mater. 13, 3351 (2001)CrossRefGoogle Scholar
  14. 14.
    J. Han, P. Fang, W. Jiang, L. Li, R. Guo, Langmuir 28, 4768 (2012)CrossRefGoogle Scholar
  15. 15.
    W. Zhou, I.E. Wachs, C.J. Kiely, Curr. Opin. Solid State Mater. Sci. 16, 10 (2012)CrossRefGoogle Scholar
  16. 16.
    S. Minakata, M. Komatsu, Chem. Rev. 109, 711 (2009)CrossRefGoogle Scholar
  17. 17.
    J.H. Clark, Acc. Chem. Res. 35, 791 (2002)CrossRefGoogle Scholar
  18. 18.
    G. Neri, G. Rizzo, A.S. Arico, C. Crisafulli, L. De Luca, A. Donato, M.G. Musolino, R. Pietropaolo, Appl. Catal. A Gene. 325, 15 (2007)CrossRefGoogle Scholar
  19. 19.
    A. Khalafi-Nezhad, E.S. Shahidzadeh, S. Sarikhani, F. Panahi, J. Mol. Catal. A: Chem. 379, 1 (2013)CrossRefGoogle Scholar
  20. 20.
    A.P. Kozikowski, S. Tapadar, D.N. Luchini, K.H. Kim, D.D. Billadeau, J. Med. Chem. 51, 4370 (2008)CrossRefGoogle Scholar
  21. 21.
    B.H. Norman, P.A. Lander, J.M. Gruber, J.S. Kroin, J.D. Cohen, L.N. Jungheim, J.S. Starling, K.L. Law, T.D. Self, L.B. Tabas, D.C. Williams, D.C. Paul, A.H. Dantzig, Bioorg. Med. Chem. Lett. 15, 1526 (2005)CrossRefGoogle Scholar
  22. 22.
    S. Batra, S.K. Rastogi, B. Kundu, A. Patra, A.P. Bhaduri, Tetrahed Lett. 41(31), 5971 (2000)CrossRefGoogle Scholar
  23. 23.
    A. Barria, V. Derkach, T. Soderling, J. Biol. Chem. 272, 32727 (1997)CrossRefGoogle Scholar
  24. 24.
    Y.K. Kang, K.J. Shin, K.H. Yoo, K.J. Seo, C.Y. Hong, C.S. Lee, S.Y. Park, D.J. Kim, S.W. Park, Bioorg. Med. Chem. Lett. 10, 95 (2000)CrossRefGoogle Scholar
  25. 25.
    C.V. Vicentini, C. Romagnoli, S. Manfredini, D. Rossi, D. Mares, Pharm. Biol. 49(5), 545 (2011)CrossRefGoogle Scholar
  26. 26.
    R.K. Reddy, S.P. Rao, J.G. Dev, Y. Poornachandra, G.C. Kumar, S.P. Rao, B.B. Narsaiah, Bioorg. Med. Chem. Lett. 24(7), 1661 (2014)CrossRefGoogle Scholar
  27. 27.
    A. Padmaja, C. Rajasekhar, A. Muralikrishna, V. Padmavathi, Eur. J. Med. Chem. 46, 5034 (2011)CrossRefGoogle Scholar
  28. 28.
    D.A. Patrick, S.A. Bakunov, S.M. Bakunova, E.V. Kumar, R.J. Lombardy, S.K. Jones, A.S. Bridges, O. Zhirnov, J.E. Hall, T. Wenzler, R. Brun, R.R. Tidwell, J. Med. Chem. 50(10), 2468 (2007)CrossRefGoogle Scholar
  29. 29.
    B. Loh, L. Vozzolo, B.J. Mok, C.C. Lee, R.J. Fitzmaurice, S. Caddick, A. Fassati, Chem. Biol. Drug Des. 75(5), 461 (2010)CrossRefGoogle Scholar
  30. 30.
    J. Mao, H. Yuan, Y. Wang, B. Wan, M. Pieroni, Q. Huang, R.B. van Breemen, A.P. Kozikowski, S.G. Franzblau, J. Med. Chem. 52(22), 6966 (2009)CrossRefGoogle Scholar
  31. 31.
    Y. Karabasanagouda, A.V. Adhikari, M. Girisha, Indian J. Chem. 48B, 430 (2009)Google Scholar
  32. 32.
    B.L. Deng, M.D. Cullen, Z. Zhou, T.L. Hartman, R.W. Buckheit Jr, C. Pannecouque, E. Declescq, P.E. Fanwick, M. Cushman, Bioorg. Med. Chem. 14, 2366 (2006)CrossRefGoogle Scholar
  33. 33.
    H. Kiyani, F. Ghorbani, Heterocyc. Lett. 3(3), 359 (2013)Google Scholar
  34. 34.
    K. Ablajan, H. Xiamuxi, Synth. Commun. 42, 1128 (2012)CrossRefGoogle Scholar
  35. 35.
    Q. Liu, R-T. Wu, J. Chem. Res. 598 (2011)Google Scholar
  36. 36.
    Q. Liu, Y.-N. Zhang, Bull. Korean Chem. Soc. 32(10), 3559 (2011)CrossRefGoogle Scholar
  37. 37.
    Z. Ying-Qun, M.A. Jing-Jun, W.L.I. Chun, Z. Jing-Ci, Z. Dong-Nuan, L. Xiao-Huan, L. Jie, Chin. J. Org. Chem. 28, 141 (2008)Google Scholar
  38. 38.
    K. Ablajan, H. Xiamuxi, Chin. Chem. Lett. 22, 151 (2011)CrossRefGoogle Scholar
  39. 39.
    M. Mirzazadeh, G.H. Mahdavinia, Eur. J. Chem. 9(1), 425 (2012)Google Scholar
  40. 40.
    F. Saikh, J. Das, S. Ghosh, Tetrahedr. Lett. 54, 4679 (2013)CrossRefGoogle Scholar
  41. 41.
    H. Kiyani, F. Ghorbani, Org. Chem. Indian J. 9(9), 97 (2013)Google Scholar
  42. 42.
    H. Kiyani, F. Ghorbani, Open. J. Org. Chem. 1(1), 5 (2013)Google Scholar
  43. 43.
    Q. Liu, X. Hou, Phosph. Sulf. Silicon. 187, 448 (2012)CrossRefGoogle Scholar
  44. 44.
    C. Qingfang, X. Xingyou, W. Qifa, L. Lisha, L. Wangjun, L. Qiao, Y. Xujie, Chin. J. Org. Chem. 8, 1267 (2009)Google Scholar
  45. 45.
    H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 8, 45 (2013)Google Scholar
  46. 46.
    S. Maddila, R. Pagadala, S.B. Jonnalagadda, Lett. Org. Chem. 10(10), 693 (2013)CrossRefGoogle Scholar
  47. 47.
    S. Maddila, S. Rana, R. Pagadala, S.B. Jonnalagadda, Res. Chem. Intermed. (2014). doi: 10.1007/s11164-014-1890-4 Google Scholar
  48. 48.
    R. Pagadala, S. Maddila, S.B. Jonnalagadda, Catal. Commun. 45, 148 (2014)CrossRefGoogle Scholar
  49. 49.
    R. Pagadala, S. Maddila, V. Moodley, W.E. van Zyl, S.B. Jonnalagadda, Tetrahed. Lett. 55, 4006 (2014)CrossRefGoogle Scholar
  50. 50.
    S. Maddila, V.D.B.C. Dasireddy, S.B. Jonnalagadda, Appl. Catal. B Environ. 138–139, 149 (2013)CrossRefGoogle Scholar
  51. 51.
    E.C. Chetty, S. Maddila, C. Southway, S.B. Jonnalagadda, Ind. Eng. Chem. Res. 51, 2864 (2012)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  • Surya Narayana Maddila
    • 1
  • Suresh Maddila
    • 1
  • Werner E. van Zyl
    • 1
  • Sreekantha B. Jonnalagadda
    • 1
    Email author
  1. 1.School of Chemistry and PhysicsUniversity of KwaZulu-NatalDurbanSouth Africa

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