Inorganic Chemistry Research

Nano-Ferrite ZnFe2O4: as Efficient and Re-Usable Catalyst for the synthesis of 4H-Chromenes and 4H-Pyrano[2,3-c]pyrazoles

Document Type : Research Paper

Author

Faculty of Sciences, Department of Chemistry, Kosar University of Bojnord, Iran

10.22036/icr.2021.304989.1118

Abstract

Nano-magnetic ferrite ZnFe2O4 among other magnetic nanoparticles include Fe2O3, Fe3O4, Ni(0.7)Zn(0.3)Fe2O4 and Mn(0.7)Zn(0.3)Fe2O4 was explored as an efficient catalyst for the synthesis of various 4H-Chromenes and 4H-Pyrano[2,3-c]pyrazoles in EtOH/H2O (2:1) via an easy and green procedure. The desired products were obtained in high yields via a three-component reaction between aromatic aldehydes with malononitrile and 5,5-dimethyl-cyclohexane-1,3-dione or 3-methyl-1-phenyl-2-pyrazolin-5-one at room temperature. The structure of this catalyst was fully characterized via Fourier transform infrared spectroscopy, XRD, SEM, TEM, EDAX, and VSM. The employed nanocatalyst was easily recovered using a magnetic field and reused ten times (in subsequent runs) without observation a significant decrease in activity. 

Graphical Abstract

Nano-Ferrite ZnFe2O4: as Efficient and Re-Usable Catalyst for the synthesis of 4H-Chromenes and 4H-Pyrano[2,3-c]pyrazoles

Keywords

  1. Astruc, F. Lu, J. R. Aranzaes, Angew. Chem. Int. Ed. 2005, 44, 7852-7872.
  2. T. Reetz, M. Maase, Adv. Mater. 1999, 11, 773-777.
  3. M. Choudary, M. L. Kantam, K. V. S. Ranganath, K. Mahender, B. Sreedhar, J. Am. Chem. Soc. 2004, 126, 3396-3397.
  4. M. Choudary, R. S. Mulukutla, K. J. Klabunde, J. Am. Chem. Soc. 2003, 125, 2020-2021.
  5. A. Melero, R. V. Grieken, G. Morales, Chem. Rev. 2006, 106, 3790-3812.
  6. Morent, S. Vasseur, F. Grasset, E. Duguet, J. Mater. Chem. 2004, 14, 2161-2175.
  7. Polshettiwar, B. Baruwati, R. S. Varma, Green Chem. 2009, 11, 127-131.
  8. J. Amali, R. K. Rana, Green Chem. 2009, 11, 1781-1795.
  9. Baruwati, V. Polshettiwar, R. S. Varma, Tetrahedron Lett. 2009, 50, 1215-1218.
  10. Polshettiwar, R. S. Varma, Org. Biomol. Chem. 2009, 7, 37-40.
  11. Shylesh, J. Schweizer, S. Demeshko, V. Schunemann, S. Ernst, W. R. Thiela, Adv. Synth. Catal. 2009, 351, 1789-1795.
  12. G. Hu, G. T. Yee, W. B. Lin, J. Am. Chem. Soc. 2005, 127, 12486-12487.
  13. Chahkandi, A. Amiri, Inorg. Chem. Res. 2019, 2, 50-64.
  14. Mohammadnezhada, F. Ariaeinezhada, F. Steiniger, Inorg. Chem. Res. 2019, 2, 129-136.15.
  15. Ahmadi, M. Bahadori, V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpoor-Baltork, Inorg. Chem. Res. 2020, 4, 51-65.
  16. Rafiee, S. Kazemi, S. Eavani, Inorg. Chem. Res. 2020, 4, 1-9.
  17. Keshavarzipour, H. Tavakol, Appl. Organometal Chem. 2016, 31, 1-8.
  18. Tavakol, F. Keshavarzipour, Appl. Organometal Chem. 2017, 31, 1-9.
  19. B. N. Baig, R. S. Varma, Chem. Commun. 2012, 48, 2582-2584.
  20. Maleki, Z. Varzi, F. Hassanzadeh-Afruzi, Polyhedron, 2019, 171, 193-202.
  21. Taqi Jafari-Chermahini, H. Tavakol, Chem. Select. 2019, 4, 1895-1902.
  22. Cullity, Elements of X-Ray Diffraction, Addison Wesley Inc, 1977.
  23. Sreekumar, T. Raja, B. Kiran, S. Sugunan, B. Rao, Appl. Catal. A. 1999, 182, 327-336.
  24. B. Bersuker, Electronic Structure and Properties of Transition Metal Compounds: Introduction to the Theory, New York, Wiley, 1996.
  25. Burns, Mineralogical Applications of Crystal Field Theory, Cambridge: Cambridge University Press, 1993.
  26. J. Borg, G. J. Dienes, Physical Chemistry of Solids (Academic: San Diego, CA), 1992.
  27. Goldman, Modem Ferrite Technology, 2nd ed., P. A. Pittsburgh, USA, 1987.
  28. Zhu, K. J. Tseng, IEEE Trans. Magn. 2004, 40, 3339-3345.
  29. Dömling, I. Ugi, Angew. Chem. Int. Ed. 2000, 39, 3168-3210.
  30. Ganem, Acc. Chem. Res. 2009, 42, 463-472.
  31. Brase, C. Gil, K. Knepper, Bioorg. Med. Chem. 2002, 10, 2415-2437.
  32. L. Andreani, E. Lapi, Bull. Chim. Farm. 1960, 99, 583-586.
  33. Gao, C. H. Tsai, C. Tseng, C. F. Yao, Tetrahedron, 2008, 64, 9143-9149.
  34. Kumar, V. B. Reddy, S. Sharad, U. Dube, S. Kapur, Eur. J. Med. Chem. 2009, 44, 3805.
  35. Shi, J. Mou, Q. Zhuang, L. Niu, N. Wu, X. Wang, Synth. Commun. 2004, 34, 4557-4263.
  36. S. Jin, A. Q. Wang, Z. L. Cheng, J. S. Zhang, T. Li, Synth. Commun. 2005, 35, 137-143.
  37. B. Guo, S. X. Wang, J. T. Li, Synth.Commun. 2007, 37, 2111-2120.
  38. Azarifar, R. Nejat-Yami, D. Azarifar, J. Iran. Chem. Soc. 2013, 10, 439-446.
  39. S. Jin, R. Q. Zhao, T. S. Li, Arkivoc, 2006, 11, 176-182.
  40. Sheibani, M. Babaie, Synth. Commun. 2010, 40, 257-265.
  41. Azarifar, R. Nejat-Yami, M. A. Zolfigol, J. Heterocycl. Chem. 2013, 50, 1386-1390.
  42. A. Zolfigol, T. Azadbakht, V. Khakyzadeh, R. Nejat Yami, D. M. Perrin, RSC Adv. 2014, 4, 40036-40042.
  43. Azarifar, R. Nejat-Yami, Z. Akrami, F. Sameri, S. Samadi, Lett. Org. Chem. 2012, 9, 128-132.
  44. Balali, M. Bagherzadeh, R. Nejat, H. Keypour, Inorg. Chem. Res. 2021, 5, 82-93.
  45. Khaksar, A. Rouhollahpour, S. M. Talesh, J. Fluorine Chem. 2012, 141, 11-15.
  46. Azarifar, Y. Abbasi, O. Badalkhani, J. Adv. Chem. 2014, 10, 3197-3202.
  47. Fang, H. B. Zhang, Z. L. Liu, J. Heterocycl. Chem. 2010, 47, 63-67.
  48. Azarifar, S. M. Khatami, R. Nejat-Yami, J. Chem. Sci. 2014, 126, 95-101.
  49. C. Xu, W. M. Li, Z. Zheng, Y. F. Lai, P. F. Zhang, Tetrahedron. 2011, 67, 9582-9587.
  50. Q. Yu, F. Liu, Q. D. You, Org. Prep. Proced. Int. 2009, 41, 77-82.
  51. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, P. Salehi, Synth. Commun. 2007, 37, 1097-1108.
  52. Sarrafi, E. Mehrasbi, A. Vahid, M. Tajbakhsh, Chin. J. Catal. 2012, 33, 1486-1494.
  53. S. Jin, A. Q. Wang, Z. L. Cheng, J. S. Zhang, T. S. Li, Synth. Commun. 2005, 35, 137-143.
  54. B. Guo, S. X. Wang, J. T. Li, Synth. Commun. 2007, 37, 2111-2120.
  55. G. Sharanina, V. K. Promonenkov, V. P. Marshtupa, A. V. Pashchenko, V. V. Puzanova, Yu. A. Sharanin, N. A. Klyuev, L. F. Gusev, A. P. Gnatusina, Chem. Het. Comp. 1982, 18, 1-7.
  56. Saha, S. Payra, S. Banerjee, Green Chem. 2015, 17, 2859-2866.
  57. Farahi, B. Karami, I. Sedighimehr, H. Mohamadi Tanuraghaj, Chin. Chem. Lett. 2014, 25, 1580-1582.
  58. Saha, S. Payra, S. Banerjee, Green Chem. 2015, 17, 2859-2866.
  59. M. Silverstein, F. X. Webster, D. J. Kiemle, D. L. Bryce, Spectrometric Identification of Organic Compounds, Wiley, New York, 2014.
  60. A. Hosseini, V. Majidi, A. R. Abbasian, J. Sulfur. Chem. 2018, 39, 119-129.
  61. Kurian, M. J. Mathew, J. Magn. Magn. Mater. 2018, 451, 121-130.
  62. Araghi, M. Ghahari, M. S. Afarani, J. Environ. Chem. Eng. 2017, 5, 1780-1790.
  63. M. Naiini, M. Ghahari, M. S. Afarani, Part Sci. Technol. 2015, 33, 456-462.
  64. R. Amiri, M. H. Yousefi, M. R. Abolhassani, S. Manouchehri, M. H. Keshavarz, S. Fatahian, J. Magn. Magn. Mater. 2011, 323, 730-734.
  65. Li, H. Wang, L. Wang, J. Wang, J. Magn. Magn. Mater. 2007, 309, 295-299.
  66. Massart, IEEE Trans. Magn. 1981, 17, 1247-1248.
  67. Predescu, Bulletin of the Polytechnic Institute of Jassy, LVI (LX), 2010, 2, 95-102.
  68. A. Legodi, D. de Waal, Dyes Pigments. 2007, 74, 161-168.
  69. L. A. Faria, S. V. Silva, M. T. Oliveira, J. Raman. Spectrosc. 1997, 28, 873-878.
Inorganic Chemistry Research
Volume 6, Issue 1
Spring and Summer; Special Issue: In Memory of Prof. Mehdi Rashidi
2022
Pages 10-16
  • Receive Date: 15 September 2021
  • Revise Date: 24 December 2021
  • Accept Date: 24 December 2021
  • First Publish Date: 05 January 2022