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Fe3O4-supported N-pyridin-4-amine-grafted graphene oxide as efficient and magnetically separable novel nanocatalyst for green synthesis of 4H-chromenes and dihydropyrano[2,3-c]pyrazole derivatives in water

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Abstract

Fe3O4-magnetized N-pyridin-4-amine-functionalized graphene oxide [Fe3O4@GO-N-(pyridin-4-amine)] was readily prepared via a three-step procedure. The synthesized nanofilms were characterized by scanning electron microscopy, powder X-ray diffraction analysis, Fourier-transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, vibrating-sample magnetometry, and elemental analysis. The prepared magnetic amine-functionalized graphene oxide exhibited high catalytic activity for one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and tetrahydrobenzo[b]pyran (4H-chromene) derivatives. Excellent product yield, short reaction time, use of water as green solvent, and easy workup procedure are the main advantages of the present protocol. In addition, the catalyst could be easily separated by magnetic decantation and reused for six cycles without significant loss of catalytic activity.

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References

  1. K. Tanaka, F. Toda, Chem. Rev. 100, 1025 (2000)

    Article  CAS  PubMed  Google Scholar 

  2. P.T. Anastas, J.C. Warner, Green Chemistry, Theory and Practice (Oxford University Press, Oxford, 1998)

    Google Scholar 

  3. P.T. Anastas, T. Williamson, Green Chemistry, Frontiers in Benign Chemical Synthesis and Process (Oxford University Press, Oxford, 1998)

    Google Scholar 

  4. G.A. Olah, A. Molnar, Hydrocarbon Chemistry (Wiley, New York, 1995)

    Google Scholar 

  5. A. Schatz, O. Reiser, W.J. Stark, Chem. Eur. J. 16, 8950 (2010)

    Article  CAS  PubMed  Google Scholar 

  6. N. Yan, C.X. Xiao, Y.K. Coord, Chem. Rev. 254, 1179 (2010)

    CAS  Google Scholar 

  7. C.O. Dalaigh, S.A. Corr, Y.G. Ko, S.J. Connon, Angew. Chem. Int. Ed. 46, 4329 (2007)

    Article  CAS  Google Scholar 

  8. F. Shi, M.K. Tse, M.M. Pohl, A. Bruckner, S. Zhang, M. Beller, Angew. Chem. Int. Ed. 46, 8866 (2007)

    Article  CAS  Google Scholar 

  9. D.H. Zhang, G.D. Li, J.X. Li, J.S. Chen, Chem. Commun. 29, 3414 (2008)

    Article  CAS  Google Scholar 

  10. M.R. Hoffman, S.T. Martin, W.D. Choi, W. Bahnemann, Chem. Rev. 95, 69 (1995)

    Article  Google Scholar 

  11. A. Saxena, A. Kumar, S. Mozumdar, J. Mol. Catal. A: Chem. 269, 35 (2007)

    Article  CAS  Google Scholar 

  12. A.T. Bell, Science 299, 1688 (2003)

    Article  CAS  Google Scholar 

  13. S. Shylesh, J. Schweizer, S. Demeshko, V. Schunemann, S. Ernst, W.R. Thiela, Adv. Synth. Catal. 351, 1789 (2009)

    Article  CAS  Google Scholar 

  14. V. Polshettiwar, R.S. Varma, Green Chem. 12, 743 (2010)

    Article  CAS  Google Scholar 

  15. D. Guin, B. Baruwati, S.V. Manorama, Org. Lett. 9, 1419 (2007)

    Article  CAS  PubMed  Google Scholar 

  16. C.W. Lim, I.S. Lee, Nano Today. 5, 412 (2010)

    Article  CAS  Google Scholar 

  17. S. Shylesh, V. Schunemann, W.R. Thiel, Angew. Chem. 49, 3428 (2010)

    Article  CAS  Google Scholar 

  18. Y.H. Zhu, L.P. Stubbs, F. Ho, R.Z. Liu, C.P. Ship, J.A. Maguire, N.S. Hosmane, ChemCatChem 2, 365 (2010)

    Article  CAS  Google Scholar 

  19. V. Polshettiwar, R. Luque, A. Fihri, H.B. Zhu, M. Bouhrara, J.M. Bassett, Chem. Rev. 111, 3036 (2011)

    Article  CAS  Google Scholar 

  20. T.Q. Zeng, W.W. Chen, C.M. Cirtiu, A. Moores, G.H. Song, C.J. Li, Green Chem. 12, 570 (2010)

    Article  CAS  Google Scholar 

  21. L.M. Rossi, N.J.S. Costa, F.P. Silva, R.V. Goncalves, Nanotech. Rev. 2, 597 (2013)

    Article  CAS  Google Scholar 

  22. Y. Zhang, C.G. Xia, Appl. Catal. A 366, 141 (2009)

    Article  CAS  Google Scholar 

  23. S. Laurent, D. Forge, M. Port, A. Roch, C. Robic, L.V. Elst, R.N. Muller, Chem. Rev. 108, 2064 (2008)

    Article  CAS  Google Scholar 

  24. L. Ma’mani, M. Sheykhan, A. Heydari, M. Faraji, Y. Yamini, Appl. Catal. A 377, 64 (2010)

    Article  CAS  Google Scholar 

  25. B. Karimi, E. Farhangi, Chem. Eur. J. 17, 6056 (2011)

    Article  CAS  PubMed  Google Scholar 

  26. G.B. Dharma, M.P. Kaushik, A.K. Halve, Tetrahedron Lett. 53, 2741 (2012)

    Article  CAS  Google Scholar 

  27. J.M. Khurana, K. Vij, Tetrahedron Lett. 52, 3666 (2011)

    Article  CAS  Google Scholar 

  28. B. Karami, K. Eskandari, S. Khodabakhshi, Arkivoc ix, 76 (2012)

    Google Scholar 

  29. A. Rashidi, Z. Tavakoli, Y. Tarak, S. Khodabakhshi, M.K. Abbasabadi, J. Chin. Chem. Soc. 63, 399 (2016)

    Article  CAS  Google Scholar 

  30. D.R. Dreyer, S. Park, C.W. Bielawski, R.S. Ruoff, Chem. Soc. Rev. 39, 228 (2010)

    Article  CAS  Google Scholar 

  31. D.R. Dreyer, H.P. Jia, C.W. Bielawski, Angew. Chem. Int. Ed. 49, 6813 (2010)

    CAS  Google Scholar 

  32. A. Rashidi, M.K. Abbasabadi, S. Khodabakhshi, J. Nat. Gas Sci. Eng. 36, 13 (2016)

    Article  CAS  Google Scholar 

  33. K.S. Novoselov, A.K. Geim, S.V. Morozov, D. Jiang, M.I. Katsnelson, I.V. Grigorieva, S.V. Dubonos, A.A. Firsov, Nature 438, 197 (2005)

    Article  CAS  Google Scholar 

  34. K.S. Novoselov, Z. Jiang, Y. Zhang, S.V. Morozov, H.L. Stormer, U. Zeitler, J.C. Maan, G.S. Boebinger, P. Kim, A.K. Geim, Science 315, 1379 (2007)

    Article  CAS  PubMed  Google Scholar 

  35. S. Stankovich, D.A. Dikin, G.H.B. Dommett, K.M. Kohlhaas, E.J. Zimney, E.A. Stach, R.D. Piner, S.T. Nguyen, R.S. Ruoff, Nature 442, 282 (2006)

    Article  CAS  Google Scholar 

  36. M.K. Abbasabadi, A. Rashidi, J. Safaei-Ghomi, S. Khodabakhshi, R. Rahighi, J. Sulfur Chem. 36, 660 (2015)

    Article  CAS  Google Scholar 

  37. D.W. Wang, F. Li, J.P. Zhao, W.C. Ren, Z.G. Chen, J. Tan, Z.S. Wu, I. Gentle, G.Q. Lu, H.M. Cheng, ACS Nano 3, 1745 (2009)

    Article  CAS  PubMed  Google Scholar 

  38. I.V. Lightcap, T.H. Kosel, P.V. Kamat, Nano Lett. 10, 577 (2010)

    Article  CAS  Google Scholar 

  39. F. Hu, M. Patel, F. Luo, C. Flach, R. Mendelsohn, E. Garfunkel, H. He, M. Szostak, J. Am. Chem. Soc. 137, 14473 (2015)

    Article  CAS  PubMed  Google Scholar 

  40. S. Khodabakhshi, F. Marahel, A. Rashidi, M.K. Abbasabadi, J. Chin. Chem. Soc. 62, 389 (2015)

    Article  CAS  Google Scholar 

  41. B. Majumdar, D. Sarma, T. Bhattacharya, T.K. Sarma, A.C.S. Sustain. Chem. Eng. 5, 9286 (2017)

    Article  CAS  Google Scholar 

  42. H. Hea, J. Klinowskia, M. Forsterb, A. Lerfb, Chem. Phys. Lett. 287, 53 (1998)

    Article  Google Scholar 

  43. L. Alvey, S. Prado, B. Saint-Joanis, S. Michel, M. Koch, S.T. Cole, F. Tillequin, Y.L. Janin, Eur. J. Med. Chem. 44, 2497 (2009)

    Article  CAS  Google Scholar 

  44. T. Narender, S.Gupta Shweta, Bioorg. Med. Chem. Lett. 14, 3913 (2004)

    Article  CAS  Google Scholar 

  45. H. Gourdeau, L. Leblond, B. Hamelin, C. Desputeau, K. Dong, I. Kianicka, D. Custeau, C. Boudreau, L. Geerts, S.X. Cai, J. Drewe, D. Labrecque, S. Kasibhatla, B. Tseng, Mol. Cancer Ther. 3, 1375 (2004)

    CAS  PubMed  Google Scholar 

  46. V.K. Tandon, M. Vaish, S. Jain, D.S. Bhakuni, R.C. Srimal, Indian J. Pharm. Sci. 53, 22 (1991)

    CAS  Google Scholar 

  47. M. Rueping, E. Sugiono, E. Merino, Chem. Eur. J. 14, 6329 (2008)

    Article  CAS  PubMed  Google Scholar 

  48. M.T. Flavin, J.D. Rizzo, A. Khilevich, A. Kucherenko, A.K. Sheinkman, V. Vilaychack, L. Lin, W. Chen, E.M. Greenwood, T. Pengsuparp, J.M. Pezzuto, S.H. Hughes, T.M. Flavin, M. Cibulski, W.A. Boulanger, R.L. Shone, Z.Q. Xu, J. Med. Chem. 39, 1303 (1996)

    Article  CAS  PubMed  Google Scholar 

  49. M. Longobardi, A. Bargagna, E. Mariani, P. Schenone, S. Vitagliano, L. Stella, A. Di Sarno, E. Marmo, Farmaco 45, 399 (1990)

    CAS  PubMed  Google Scholar 

  50. J.M. Doshi, D. Tian, C. Xing, J. Med. Chem. 49, 7731 (2006)

    Article  CAS  PubMed  Google Scholar 

  51. M.N. Erichsen, T.H.V. Huynh, B. Abrahamsen, J.F. Bastlund, C. Bundgaard, O. Monrad, A. Bekker-Jensen, C.W. Nielsen, K. Frydenvang, A.A. Jensen, L. Bunch, J. Med. Chem. 53, 7180 (2010)

    Article  CAS  PubMed  Google Scholar 

  52. S.J. Mohr, M.A. Chirigos, F.S. Fuhrman, J.W. Pryor, Cancer Res. 35, 3750 (1975)

    CAS  PubMed  Google Scholar 

  53. L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517 (1993)

    Article  CAS  Google Scholar 

  54. D.O. Moon, K.C. Kim, C.Y. Jin, M.H. Han, C. Park, K.J. Lee, Y.M. Park, Y.H. Choi, G.Y. Kim, Int. Immunopharmacol. 7, 222 (2007)

    Article  CAS  PubMed  Google Scholar 

  55. L.L. Andreani, E. Lapi, Bull. Chim. Farm. 99, 583 (1960)

    Google Scholar 

  56. Y. Peng, G. Song, Catal. Commun. 8, 111 (2007)

    Article  CAS  Google Scholar 

  57. B.N. Seshu, N. Pasha, R.K.T. Venkateswara, P.P.S.N. Lingaiah, Tetrahedron Lett. 49, 2730 (2008)

    Article  CAS  Google Scholar 

  58. T.S. Jin, L.B. Liu, Y. Zhao, T.S. Li, Synth. Commun. 35, 1859 (2005)

    Article  CAS  Google Scholar 

  59. S. Banerjee, A. Horn, H.G. Khatri, Tetrahedron Lett. 52, 1878 (2011)

    Article  CAS  Google Scholar 

  60. L.M. Fotouhi, M. Heravi, A. Fatehi, K. Bakhtiari, Tetrahedron Lett. 48, 5379 (2007)

    Article  CAS  Google Scholar 

  61. F. Khorami, H.R. Shaterian, Chin. J. Catal. 35, 242 (2014)

    Article  CAS  Google Scholar 

  62. N.M.A. bdEi-Rahman, A.A. Ei-Kateb, M.F. Mady, Synth. Commun. 37, 3961 (2007)

    Article  CAS  Google Scholar 

  63. M. Khoobi, L. Ma’mani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. Mol. Catal. A: Chem. 359, 74 (2012)

    Article  CAS  Google Scholar 

  64. J.L. Wang, D. Liu, Z.J. Zhang, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri, Z. Huang, Proc. Natl. Acad. Sci. U. S. A. 97, 7124 (2000)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  65. M.E.A. Zaki, H.A. Soliman, O.A. Hiekal, Z.A.E. Rashad, Naturforsch. C 61, 1 (2006)

    Article  CAS  Google Scholar 

  66. C.B. Sangani, D.C. Mungra, M.P. Patel, R.G. Patel, Chin. Chem. Lett. 23, 57 (2012)

    Article  CAS  Google Scholar 

  67. A.K. Elziaty, O.E.A. Mostafa, E.A. El-Bordany, M. Nabil, H.M.F. Madkour, Int. J. Sci. Eng. Res. 5, 727 (2014)

    Google Scholar 

  68. S.C. Kuo, L.J. Huang, H. Nakamura, J. Med. Chem. 27, 539 (1984)

    Article  CAS  PubMed  Google Scholar 

  69. D. Azarifar, Y. Abbasi, Synth. Commun. 46, 745 (2016)

    Article  CAS  Google Scholar 

  70. M.S. Shingare, D.V. Mane, Chin. Chem. Lett. 21, 1175 (2010)

    Article  CAS  Google Scholar 

  71. G. Vasuki, K. Kumaravel, Tetrahedron Lett. 49, 5636 (2008)

    Article  CAS  Google Scholar 

  72. S. Gogoi, C.G. Zhao, Tetrahedron Lett. 50, 2252 (2009)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  73. H. Sheibani, M. Babaie, Synth. Commun. 40, 257 (2010)

    Article  CAS  Google Scholar 

  74. T.S. Jin, R.Q. Zhao, T.S. Li, Arkivoc xi, 176 (2006)

    Google Scholar 

  75. D. Azarifar, M. Tadayoni, M. Ghaemi, Appl. Organomet. Chem. 32, e4293 (2018)

    Article  CAS  Google Scholar 

  76. D. Azarifar, R. Nejat-Yami, M. AlKobaisi, J. Iran. Chem. Soc. 10, 439 (2013)

    Article  CAS  Google Scholar 

  77. D. Azarifar, S.M. Khatami, R. Nejat-Yami, J. Chem. Sci. 126, 95 (2014)

    Article  CAS  Google Scholar 

  78. D. Azarifar, R. Nejat-Yami, F. Sameri, Z. Akrami, Lett. Org. Chem. 9, 435 (2012)

    Article  CAS  Google Scholar 

  79. D. Azarifar, M. Ghaemi, M. Golbaghi, R. Karamian, M. Asadbegy, RSC Adv. 6, 92028 (2016)

    Article  CAS  Google Scholar 

  80. S. Khodabakhshi, M. Khaleghi Abbasabadi, S. Heydarianc, S. Gharehzadeh Shirazi, F. Marahel, Lett. Org. Chem. 12, 465 (2015)

    Article  CAS  Google Scholar 

  81. W.S.J. Hummers, R.E. Offeman, J. Am. Chem. Soc. 80, 1339 (1958)

    Article  CAS  Google Scholar 

  82. M.K. Abbasabadi, A. Rashidi, S. Khodabakhshi, J. Nat. Gas Sci. Eng. 28, 87 (2016)

    Article  CAS  Google Scholar 

  83. E. Rodrigo, B.G. Alcubilla, R. Sainz, J.L.G. Fierro, R. Ferritto, M. BeleńCid, Chem. Commun. 50, 6270 (2014)

    Article  CAS  Google Scholar 

  84. M.Z. Kassaee, E. Motamedi, M. Majdi, Chem. Eng. J. 172, 540 (2011)

    Article  CAS  Google Scholar 

  85. G. Chen, S. Zhai, Y. Zhai, K. Zhang, Q. Yue, L. Wang, J. Zhao, H. Wang, J. Liu, J. Jia, Biosens. Bioelectron. 26, 3136 (2011)

    Article  CAS  PubMed  Google Scholar 

  86. L.Z. Bai, D.L. Zhao, Y. Xu, J.M. Zhang, Y.L. Gao, L.Y. Zhao, J.T. Tang, Mater. Lett. 68, 399 (2012)

    Article  CAS  Google Scholar 

  87. S. Khodabakhshi, B. Karami, New J. Chem. 38, 3586 (2014)

    Article  CAS  Google Scholar 

  88. C. Hou, Q. Zhang, M. Zhu, Y. Li, H. Wang, Carbon 49, 47 (2011)

    Article  CAS  Google Scholar 

  89. D. Azarifar, Y. Abbasi, O. Badalkhani, J. Adv. Chem. 10, 3197 (2014)

    Article  Google Scholar 

  90. D. Fang, H.B. Zhang, Z.L. Liu, J. Hetrocycl. Chem. 47, 63 (2010)

    CAS  Google Scholar 

  91. S. Khaksar, A. Rouhollahpour, S.M. Talesh, J. Fluor. Chem. 141, 11 (2012)

    Article  CAS  Google Scholar 

  92. S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, P. Salehi, Synth. Commun. 37, 1097 (2007)

    Article  CAS  Google Scholar 

  93. S. Sarrafi, E. Mehrasbi, A. Vahid, M. Tajbakhsh, Chin. J. Catal. 33, 1486 (2012)

    Article  CAS  Google Scholar 

  94. T.S. Jin, A.Q. Wang, Z.L. Cheng, J.S. Zhang, T.S. Li, Synth. Commun. 35, 137 (2005)

    Article  CAS  Google Scholar 

  95. S.B. Guo, S.X. Wang, J.T. Li, Synth. Commun. 37, 2111 (2007)

    Article  CAS  Google Scholar 

  96. L.G. Sharanina, V.K. Promonenkov, V.P. Marshtupa, A.V. Pashchenko, V.V. Puzanova, A.Y. Sharanin, N.A. Klyuev, L.F. Gusev, A.P. Gnatusina, Chem. Heterocycl. Compd. 18, 607 (1982)

    Article  Google Scholar 

  97. A. Saha, S. Payra, S. Banerjee, Green Chem. 17, 2859 (2015)

    Article  CAS  Google Scholar 

  98. M. Farahi, B. Karami, I. Sedighimehr, H. Mohamadi Tanuraghaj, Chin. Chem. Lett. 25, 1580 (2014)

    Article  CAS  Google Scholar 

  99. M. Kangani, N. Hazeri, M. Taher Maghsoodlou, J. Chin. Chem. Soc. 63, 896 (2016)

    Article  CAS  Google Scholar 

  100. S.S. Pourpanah, S.M. Habibi-Khorassani, M. Shahraki, Chin. J. Catal. 36, 757 (2015)

    Article  CAS  Google Scholar 

  101. A.A. Mohammadi, M.R. Asghariganjeh, A. Hadadzahmatkesh, Arab. J. Chem. 10, S2213 (2017)

    Article  CAS  Google Scholar 

  102. J. Yang, S. Liu, H. Hu, S. Ren, A. Ying, Chin. J. Chem. Eng. 23, 1416 (2015)

    Article  CAS  Google Scholar 

  103. A. Abdel Hamid, M. Abd-Elmonem, A.M. Hayallah, F.A. Abo Elsoud, K.U. Sadek, Chem. Sel. 2, 10689 (2017)

    CAS  Google Scholar 

  104. P.S. Sinija, K. Sreekumar, RSC Adv. 5, 101776 (2015)

    Article  CAS  Google Scholar 

  105. M. Abdollahi-Alibeik, A. Moaddeli, K. Masoomi, RSC Adv. 5, 74932 (2015)

    Article  CAS  Google Scholar 

  106. K. Niknam, N. Borazjani, R. Rashidian, A. Jamali, Chin. J. Catal. 34, 2245 (2013)

    Article  CAS  Google Scholar 

  107. K.V. Aken, L. Strekowski, L. Patiny, Beilstein J. Org. Chem. 2, 3 (2006)

    PubMed  PubMed Central  Google Scholar 

  108. J. Huang, S. Ding, W. Xiao, Y. Peng, S. Deng, N. Zhang, Catal. Lett. 145, 1000 (2015)

    Article  CAS  Google Scholar 

  109. B. Xue, J. Zhu, N. Liu, Y. Li, Catal. Commun. 64, 105 (2015)

    Article  CAS  Google Scholar 

  110. H.M.A. Hassan, R.F.M. Elshaarawy, S. Kumar Dey, I. Simon, C. Janiak, Catal. Lett. 147, 1998 (2017)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors wish to thank the Research Council of Bu-Ali Sina University for financial support to carry out this research. Also, Islamic Azad University, North Tehran Branch, is sincerely appreciated for technical support.

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  1. Department of Chemistry, Bu-Ali Sina University, Hamedan, 65178, Iran

    Davood Azarifar & Masoud Khaleghi-Abbasabadi

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  1. Davood Azarifar
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Correspondence to Davood Azarifar.

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Azarifar, D., Khaleghi-Abbasabadi, M. Fe3O4-supported N-pyridin-4-amine-grafted graphene oxide as efficient and magnetically separable novel nanocatalyst for green synthesis of 4H-chromenes and dihydropyrano[2,3-c]pyrazole derivatives in water. Res Chem Intermed 45, 199–222 (2019). https://doi.org/10.1007/s11164-018-3597-4

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