Skip to main content
SpringerLink
Log in

MnO2@Zeolite-Y Nanoporous: Preparation and Application as a High Efficient Catalyst for Multi-Component Synthesis of 4-Arylidene-Isoxazolidinones

  • Original Paper
  • Published:
Silicon Aims and scope Submit manuscript

Abstract

In this project, nano-MnO2@zeolite-Y (NMOZ) was successfully prepared via hydrothermal technique and its structure was confirmed using FT-IR, XRD, FE-SEM, EDX and BET analyses. MnO2 nanoparticles stabilized on zeolite-NaY were used as nanocatalyst for efficient solventless preparation of 3,4-disubstituted isoxazole-5(4H)-one scaffolds via one-pot three-component reaction of ethyl acetoacetate, hydroxylamine hydrochloride, and aromatic aldehydes at 100 °C. One of the advantages of this new method is the non-use of a metal oxidant such as KMnO4 (greener method) and the stabilization of MnO2 to the zeolite-Y surface via ion bonding. This causes the MnO2 not be leached from the zeolite during the processes of nanocatalyst recycling in organic reactions. This simple approach also has promising features as like as safe, inexpensive and recyclable nanocatalyst, solvent-free reaction, short reaction times, high to excellent yields, and easy isolation of the products.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Moshoeshoe M, Nadiye-Tabbiruka M. S. Obuseng V (2017) Am J Mater Sci 7:196–221

  2. Tontisirin S (2015). J Porous Mater 22:437–445

    Article  CAS  Google Scholar 

  3. Kalhor M, Banibairami S, Mirshokraie SA (2018). Green Chem Lett Rev 11:334–344

    Article  CAS  Google Scholar 

  4. Kalhor M, Khodaparast N (2015). Res Chem Intermed 41:3235–3242

    Article  CAS  Google Scholar 

  5. Liang J, Liang Z, Zou R, Zhao Y (2017) Adv mater 29:1701139

  6. Perot G, Guisnet M (1990). J Mol Catal 61:173–196

    Article  CAS  Google Scholar 

  7. Lima CGS, Moreira NM, Paixão MW, Corrêa AG (2019). Curr Opin Green Sustain Chem 15:7–12

    Article  Google Scholar 

  8. Safari J, Zarnegar Z, Borjian Borujeni M (2013). Chem Pap 67:688–695

    Article  CAS  Google Scholar 

  9. Zhu Y, Shen M, Xia Y, Lu M (2015). Catal Commun 64:37–43

    Article  CAS  Google Scholar 

  10. Saputra E, Muhammad S, Sun H, Ang HM, Tade MO, Wang S (2013). Environ Sci Technol 47:5882–5887

    Article  CAS  PubMed  Google Scholar 

  11. Zhang QX, Peng D, Huang XJ (2013). Electrochem Commun 34:270–273

    Article  CAS  Google Scholar 

  12. Suib SL (2008) Porous manganese oxide octahedral molecular sieves and octahedral layered materials. Acc Chem Res 41:479–487

    Article  CAS  PubMed  Google Scholar 

  13. Liu J, Meng L, Fei Z, Dyson PJ, Jing X, Liu X (2017) MnO2 nanosheets as an artificial enzyme to mimic oxidase for rapid and sensitive detection of glutathione. Biosens Bioelectron 90:69–74

    Article  CAS  PubMed  Google Scholar 

  14. Chabre Y, Pannetier J (1995). Prog Solid State Chem 23:1–130

    Article  CAS  Google Scholar 

  15. Zhang XY, Han LQ, Sun S, Wang CY, Chen MM (2015). J Alloys Compd 653:539–545

    Article  CAS  Google Scholar 

  16. Zhang R, Yu X, Nam K. W, Ling C, Arthur T. S, Song W, Knapp A. M, Ehrlich S. N, Yang X. Q, Matsui M (2012) Electrochem Commun 23:110–113

  17. Julien C, Massot M (2002). Phys Chem Chem Phys 4:4226–4235

    Article  CAS  Google Scholar 

  18. Zsadon Jr B, Papp J, Czárán E, Papp Jr J (1990). J Mol Catal 62:321–330

    Article  CAS  Google Scholar 

  19. Bentrup U, Brückner A, Richter M, Fricke R (2001). Appl Catal B 32:229–241

    Article  CAS  Google Scholar 

  20. Richter M, Berndt H, Eckelt R, Schneider M, Fricke R (1999). Catal Today 54:531–545

    Article  CAS  Google Scholar 

  21. Endang PS, Rahadian AR, Ulva TIM, Alvin RW, Rendy MI, Nurul W (2019). Mater. Sci. Forum 964:199–208

    Article  Google Scholar 

  22. Han J, Guo H, Wang XG, Pang ML, Meng JB (2007). Chin J Chem 25:129–131

    Article  CAS  Google Scholar 

  23. Aret E, Meekes H, Vlieg E, Deroover G (2007). Dyes Pigments 72:339–344

    Article  CAS  Google Scholar 

  24. Biju S, Reddy MLP, Freire RO (2007). Inorg Chem Commun 10:393–396

    Article  CAS  Google Scholar 

  25. Zhang XH, Zhan YH, Chen D, Wang F, Wang LY (2012). Dyes Pigments 93:1408–1415

    Article  CAS  Google Scholar 

  26. Clemens Lamberth J (2018). J Heterocycl Chem 55:2035–2045

    Article  CAS  Google Scholar 

  27. Santos MM, Faria N, Iley J (2010) Reaction of naphthoquinones with substituted nitromethanes. Facile synthesis and antifungal activity of naphtho[2,3-d]isoxazole-4,9-diones. Bioorg Med Chem Lett 20:193–195

    Article  PubMed  CAS  Google Scholar 

  28. Karabasanagouda T, Adhikari AV, Girisha M (2009). Indian J Chem 48B:430–437

    CAS  Google Scholar 

  29. Kamal A, Bharathi EV, Reddy JS (2011) Synthesis and biological evaluation of 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydroquinazolinone hybrids as anticancer agents. Eur J Med Chem 46:691–703

    Article  CAS  PubMed  Google Scholar 

  30. Kan H, Adachi I, Kido R, Hirose K (1967). J Med Chem 10:411–418

    Article  Google Scholar 

  31. Diana P, Carbone A, Barraja P, Kelter G, Fiebig HH, Cirrincione G (2010) Synthesis and antitumor activity of 2,5-bis(3'-indolyl)-furans and 3,5-bis(3'-indolyl)-isoxazoles, nortopsentin analogues. Bioorg Med Chem 18:4524–4529

    Article  CAS  PubMed  Google Scholar 

  32. Ishioka T, Tanatani A, Nagasawa K, Hashimoto Y (2003). bioorg med Chem Lett 13:2655–2658

    Article  CAS  PubMed  Google Scholar 

  33. Ishioka T, Kubo A, Koiso Y, Nagasawa K, Itai A, Hashimoto Y (2002). Bioorg Med Chem 10:1555–1566

    Article  CAS  PubMed  Google Scholar 

  34. Kafle B, Aher NG, Khadka D, Park H, Cho H (2011) Isoxazol-5(4H)one derivatives as PTP1B inhibitors showing an anti-obesity effect. Chem Asian J 6:2073–2079

    Article  CAS  PubMed  Google Scholar 

  35. Panathur N, Gokhale N, Dalimba U, Koushik PV, Yogeeswari P, Sriram D (2015) New indole-isoxazolone derivatives: Synthesis, characterisation and in vitro SIRT1 inhibition studies. Bioorg Med Chem Lett 25:2768–2772

    Article  CAS  PubMed  Google Scholar 

  36. Villemin D, Martin B, Garrigues B (1993). Synth Commun 23:2251–2257

    Article  CAS  Google Scholar 

  37. Nakamura I, Okamoto M, Terada M (2010). Org Lett 12:2453–2245

    Article  CAS  PubMed  Google Scholar 

  38. Donleavy JJ, Gilbert EE (1937). J Am Chem Soc 59:1072–1076

    Article  CAS  Google Scholar 

  39. Lowe DB, Magnuson S, Qi N (2004) In vitro SAR of (5-(2H)-isoxazolonyl) ureas, potent inhibitors of hormone-sensitive lipase. Bioorg Med Chem Lett 14:3155–3159

    Article  CAS  PubMed  Google Scholar 

  40. Safari J, Ahmadzadeh M, Zarnegar Z (2016). Catal Commun 86:91–95

    Article  CAS  Google Scholar 

  41. Saikh F, Das J, Ghosh S (2013). Tetrahedron Lett 54:4679–4682

    Article  CAS  Google Scholar 

  42. Fozooni S, Gholam Hosseinzadeh N, Hamidianc H, Akhgarb MR (2013). J Braz Chem Soc 24:1649–1655

    CAS  Google Scholar 

  43. Kiyani H, Ghorbani F (2013). Heteroletters 3:145–153

    CAS  Google Scholar 

  44. Amol Khandebharad U, Sarda Swapnil R, Gill Charansingh H, Agrawal Brijmohan R (2015). Res J Chem Sci 5:27–32

    Google Scholar 

  45. Irannegad-Gheshlaghchaei N, Zare A, Sajadikhah SS, Banaei A (2018). Res Chem Intermed 44:6253–6266

    Article  CAS  Google Scholar 

  46. Ferouani G, Nacer A, Ameur N, Bachir R, Ziani-Cherif C (2017). J Chin Chem Soc 65:459–464

    Article  CAS  Google Scholar 

  47. laroum R, debache A (2018) Syn Commun 48:1876–1882

  48. Kiyani H, Ghorbani F (2016). Res Chem Intermed 42:6831–6844

    Article  CAS  Google Scholar 

  49. Vekariya RH, Patel KD, Patel HD (2016). Res Chem Intermed 42:7559–7579

    Article  CAS  Google Scholar 

  50. Liu Q, Zhang YN (2011). Bull Kor Chem Soc 32:3559–3560

    Article  CAS  Google Scholar 

  51. Rikani A, Setamdideh D (2016). Orient J Chem 32:1433–1437

    Article  CAS  Google Scholar 

  52. Patil MS, Mudaliar C, Chaturbhu GU (2017). Tetrahedron Lett 58:3256–3261

    Article  CAS  Google Scholar 

  53. Kiyani H, Kanaani A, Ajloo D, Ghorbani F, Vakili M (2015). Res Chem Intermed 41:7739–7773

    Article  CAS  Google Scholar 

  54. Khandebharad AU, Sarda SR, Gill CH, Agrawal BR (2015). Res J Chem Sci 5:27–32

    CAS  Google Scholar 

  55. Chavan AP, Pinjari AB, Mhaske PC (2015). J Heterocycl Chem 52:1911–1915

    Article  CAS  Google Scholar 

  56. Cheng QF, Liu XY, Wang QF, Liu LS, Liu WJ, Lin Q, Yang XJ (2009). Chin J Org Chem 29:1267–1271

    CAS  Google Scholar 

  57. Liu Q, Hou X (2012). Phosphorus Sulfur Silicon Relat Elem 187:448–453

    Article  CAS  Google Scholar 

  58. Kiyani H, Ghorbani F (2013). Org Chem 58:14948–14950

    Google Scholar 

  59. Ablajan K, Xiamuxi H (2011). Chin Chem Lett 22:151–154

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The gratitude of authors goes to the research commute of Chemistry Department of Payame Noor University who provided financial and technical supports for this project.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Payame Noor, P.O. BOX 19395-4697, Tehran, Iran

    Mehdi Kalhor, Sima Samiei & Seyed Ahmad Mirshokraie

Authors
  1. Mehdi Kalhor
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sima Samiei
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Seyed Ahmad Mirshokraie
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mehdi Kalhor.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kalhor, M., Samiei, S. & Mirshokraie, S.A. MnO2@Zeolite-Y Nanoporous: Preparation and Application as a High Efficient Catalyst for Multi-Component Synthesis of 4-Arylidene-Isoxazolidinones. Silicon 13, 201–210 (2021). https://doi.org/10.1007/s12633-020-00413-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12633-020-00413-5

Keywords

Search

Navigation