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Ni(II)-Schiff base/SBA-15: a nanostructure and reusable catalyst for one-pot three-component green synthesis of 3,4-dihydropyrano[3,2-c]chromene derivatives

  • Nader Noroozi PesyanEmail author
  • Ghasem Rezanejade Bardajee
  • Elmira Kashani
  • Marzieh Mohammadi
  • Hana Batmani
Article
  • 12 Downloads

Abstract

An efficient, rapid, and environmentally benign Ni(II)-Schiff base/SBA-15-catalyzed one-pot three-component cyclocondensation process was described via the reaction between malononitrile, 4-hydroxycoumarin, and various aldehydes in aqueous media for the synthesis of 3,4-dihydropyrano[3,2-c]chromene derivatives. This nanocatalyst was characterized using FT-IR, SEM, TGA, TEM, BET, AFM, and XRD techniques. It is possible to reuse the heterogeneous catalyst without any marked change in its catalytic activity at least five times. Other remarkable features of this method include excellent yields in pure form, convenient operation, a much milder procedure, short reaction time, simple workup and avoidance of hazardous reagents/solvents.

Keywords

Heterogeneous catalysis Ni(II)-Schiff base SBA-15 Green chemistry 3,4-Dihydropyrano[3,2-c]chromene 

Notes

Acknowledgements

The financial support of this work was gratefully acknowledged by the Research Council of Urmia and Payame Noor Universities.

Supplementary material

11164_2019_3954_MOESM1_ESM.pdf (2 mb)
Supplementary material 1 (PDF 2048 kb)

References

  1. 1.
    K. Kaneda, T. Mizugaki, Energy Environ. Sci. 2, 655 (2009)CrossRefGoogle Scholar
  2. 2.
    W. Zhang, Green Chem. 11, 911 (2009)CrossRefGoogle Scholar
  3. 3.
    N.R. Candeias, L.S.C. Branco, P.M.P. Gois, C.A.M. Afonso, A.F. Trindade, Chem. Rev. 109, 2703 (2009)CrossRefPubMedGoogle Scholar
  4. 4.
    B.M. Trost, Acc. Chem. Res. 35, 695 (2002)CrossRefPubMedGoogle Scholar
  5. 5.
    M. Sankar, N. Dimitratos, P.J. Miedziak, P.P. Wells, C.J. Kiely, G.J. Hutchings, Chem. Soc. Rev. 41, 8099 (2012)CrossRefPubMedGoogle Scholar
  6. 6.
    B.B. Toure, D.G. Hall, Chem. Rev. 109, 4439 (2009)CrossRefPubMedGoogle Scholar
  7. 7.
    J.D. Sunderhaus, S.F. Martin, Chem. Eur. J. 15, 1300 (2009)CrossRefPubMedGoogle Scholar
  8. 8.
    B. Ganem, Acc. Chem. Res. 42, 463 (2009)CrossRefPubMedPubMedCentralGoogle Scholar
  9. 9.
    N. Ismabery, R. Lavila, Chem. Eur. J. 14, 8444 (2008)CrossRefGoogle Scholar
  10. 10.
    B. Jiang, T. Rajale, W. Wever, S.J. Tu, G. Li, Chem. Asian J. 5, 2318 (2010)CrossRefPubMedGoogle Scholar
  11. 11.
    B. Jang, F. Shi, S.T. Tu, Curr. Org. Chem. 14, 357 (2010)CrossRefGoogle Scholar
  12. 12.
    S. Nasri, M. Bayat, J. Mol. Struct. 1164, 77 (2018)CrossRefGoogle Scholar
  13. 13.
    M.B. Gawande, V.D.B. Bonifacio, R. Luque, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42, 5522 (2013)CrossRefPubMedGoogle Scholar
  14. 14.
    H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 41, 4031 (2015)CrossRefGoogle Scholar
  15. 15.
    M.R. Bhosle, D.B. Wahul, G.M. Bondle, A. Sarkate, S.V. Tiwari, Synth. Commun. 48, 2046 (2018)CrossRefGoogle Scholar
  16. 16.
    T. Okuhara, Chem. Rev. 102, 3641 (2002)CrossRefPubMedGoogle Scholar
  17. 17.
    G.R. Green, J.M. Evans, A.K. Vong, In Comprehensive Heterocyclic Chemistry II, in A.R. Katritsky, C. Rees, E.F.V. Scriven, (Eds.), (Pergamon Press, Oxford, 1995), pp. 469Google Scholar
  18. 18.
    C. Wiener, C.H. Schroeder, B.D. West, K.P. Link, J. Org. Chem. 27, 3086 (1962)CrossRefGoogle Scholar
  19. 19.
    S.K. Kulkarni, P.N. Kaul, Indian J. Exp. Biol. 18, 270 (1980)PubMedGoogle Scholar
  20. 20.
    H. Tomoda, Y.K. Kim, H. Nishida, R. Masuma, S. Omura, J. Antibiot. 47, 148 (1994)CrossRefPubMedGoogle Scholar
  21. 21.
    M. Handa, T. Sunazuka, K. Nagai, R. Kimura, T. Shirahata, Z.M. Tian, K. Otoguro, Y. Harigaya, S. Omura, J. Antibiot. 54, 382 (2001)CrossRefPubMedGoogle Scholar
  22. 22.
    J.J. Chen, P.H. Liao, C.H. Huang, S.Y. Chen, J. Nat. Prod. 70, 1444 (2007)CrossRefPubMedGoogle Scholar
  23. 23.
    F. Koizumi, N. Fukumitsu, J. Zhao, R. Chanklan, T. Miyakawa, S. Kawahara, S. Iwamoto, M. Suzuki, S. Kakita, E.S. Rahayu, S. Hosokawa, K. Tatsuta, M. Ichimura, J. Antibiot. 60, 455 (2007)CrossRefPubMedGoogle Scholar
  24. 24.
    I.S. Chen, I.W. Tsai, C.M. Teng, J.J. Chen, Y.L. Chang, F.N. Ko, M.C. Lu, Phytochemistry 46, 525 (1997)CrossRefGoogle Scholar
  25. 25.
    C. Ito, M. Itoigawa, A. Furukawa, T. Hirano, T. Murata, N. Kaneda, Y. Hisada, K. Okuda, H. Furukawa, J. Nat. Prod. 67, 1800 (2004)CrossRefPubMedGoogle Scholar
  26. 26.
    I.S. Chen, S.J. Wu, I.L. Tsai, T.S. Wu, J.M. Pezzuto, M.C. Lu, H. Chai, N. Suh, C.M. Teng, J. Nat. Prod. 57, 1206 (1994)CrossRefPubMedGoogle Scholar
  27. 27.
    M. Seifi, H. Sheibani, Catal. Lett. 126, 275 (2008)CrossRefGoogle Scholar
  28. 28.
    M. Kidwai, S. Saxena, Synth. Commun. 36, 2737 (2006)CrossRefGoogle Scholar
  29. 29.
    J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)CrossRefGoogle Scholar
  30. 30.
    G. Brahmachari, B. Banerjee, ACS Sustain. Chem. Eng. 2, 411 (2014)CrossRefGoogle Scholar
  31. 31.
    H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 41, 7847 (2015)CrossRefGoogle Scholar
  32. 32.
    M.M. Heravi, B. Alimadadi Jani, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Catal. Commun. 10, 272 (2008)CrossRefGoogle Scholar
  33. 33.
    M. Rohaniyan, A. Davoodnia, A. Nakhaei, Appl. Organometal. Chem. 30, 626 (2016)CrossRefGoogle Scholar
  34. 34.
    J.M. Khurana, B. Nand, P. Saluja, Tetrahedron 66, 5637 (2010)CrossRefGoogle Scholar
  35. 35.
    D.Q. Shi, N. Wu, Q.Y. Zhuang, J. Chem. Res. 9, 542 (2008)CrossRefGoogle Scholar
  36. 36.
    M.M. Heravi, B.A. Jani, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Catal. Commun. 10, 272 (2008)CrossRefGoogle Scholar
  37. 37.
    M.M. Heravi, S. Sadjadi, N.M. Haj, H.A. Oskooie, F.F. Bamoharram, Catal. Commun. 10, 1643 (2009)CrossRefGoogle Scholar
  38. 38.
    A. Shaabani, S. Samadi, Z. Badri, A. Rahmati, Catal. Lett. 104, 39 (2005)CrossRefGoogle Scholar
  39. 39.
    J. Safaei-Ghomi, F. Eshteghal, H. Shahbazi-Alavi, Polycycl. Aromat. Compd. (2017).  https://doi.org/10.1080/10406638.2017.1348368 CrossRefGoogle Scholar
  40. 40.
    M.B.K. Billing, P.K. Agnihotri, N. Kaur, N. Singh, D.O. Jang, ACS Sustain. Chem. Eng. 6, 3714 (2018)CrossRefGoogle Scholar
  41. 41.
    M.A. Zolfigol, N. Bahraminejad, F. Afsharnadery, S. Baghery, J. Mol. Liq. 221, 851 (2016)CrossRefGoogle Scholar
  42. 42.
    R. Nongrum, G.S. Nongthombam, M. Kharkongor, J.W.S. Rani, N. Rahman, C. Kathing, B. Myrboh, R. Nongkhlaw, RSC Adv. 6, 108384 (2016)CrossRefGoogle Scholar
  43. 43.
    A. Mohammadinezhad, B. Akhlaghinia, Aust. J. Chem. 71, 32 (2018)CrossRefGoogle Scholar
  44. 44.
    M. Khoobi, L. Ma’mani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. Mol. Catal. A Chem. 359, 74 (2012)CrossRefGoogle Scholar
  45. 45.
    M. Esmaeilpour, J. Javidi, F. Dehghani, F. Nowroozi Dodeji, RSC Adv. 5, 26625 (2015)CrossRefGoogle Scholar
  46. 46.
    T. Baran, N. Yılmaz Baran, A. Menteş, Appl. Organomet. Chem. 32(2), e4075 (2018)CrossRefGoogle Scholar
  47. 47.
    H. Azizi, A. Khorshidi, Kh Tabatabaeian, J. Iran. Chem. Soc. 15, 1023 (2018)CrossRefGoogle Scholar
  48. 48.
    T. Baran, N.Y. Baran, A. Menteş, Int. J. Biol. Macromol. 115, 249 (2018)CrossRefPubMedGoogle Scholar
  49. 49.
    N.Y. Baran, T. Baran, A. Menteş, Carbohydr. Polym. 181, 596 (2018)CrossRefPubMedGoogle Scholar
  50. 50.
    T. Baran, Carbohydr. Polym. 195, 45 (2018)CrossRefPubMedGoogle Scholar
  51. 51.
    T. Baran, Ultrason. Sonochem. 45, 231 (2018)CrossRefPubMedGoogle Scholar
  52. 52.
    N. Zhang, Y.H. Fan, Z. Zhang, J. Zuo, P.F. Zhang, Q. Wang, S.B. Liu, C.F. Bi, Inorg. Chem. Commun. 22, 68 (2012)CrossRefGoogle Scholar
  53. 53.
    M. Salavati-Niasari, A. Amiri, Appl. Catal. A Gen. 290(46), 46 (2005)CrossRefGoogle Scholar
  54. 54.
    Z.Y. Li, R.R. Tang, G.Y. Liu, Catal. Lett. 143, 592 (2013)CrossRefGoogle Scholar
  55. 55.
    K.C. Gupta, H.K. Abdul Kadir, S. Chand, Macromol. Sci. A Pure Appl. Chem. 39, 1451 (2002)CrossRefGoogle Scholar
  56. 56.
    C. Jin, W. Fan, Y. Jia, B. Fan, J. Ma, R. Li, J. Mol. Catal. A Chem. 249, 23 (2006)CrossRefGoogle Scholar
  57. 57.
    R. Liu, Y. Zhang, P.Y. Feng, J. Am. Chem. Soc. 131, 15128 (2009)CrossRefPubMedGoogle Scholar
  58. 58.
    V. Meynen, P. Cool, E.F. Vansant, Microporous Mesoporous Mater. 125, 170 (2009)CrossRefGoogle Scholar
  59. 59.
    H. Batmani, N.N. Pesyan, F. Havasi, Microporous Mesoporous Mater. 257, 27 (2018)CrossRefGoogle Scholar
  60. 60.
    M. Mirza-Aghayan, S. Nazmdeh, R. Boukherroub, M. Rahimifard, A.A. Tarlani, M. Abolghasemi-Malakshah, Synth. Commun. 43, 1499 (2013)CrossRefGoogle Scholar
  61. 61.
    S.M. Bruno, J.A. Fernandes, L.S. Martins, I.S. Gonçalves, M. Pillinger, P. Ribeiro-Claro, J. Rocha, A.A. Valente, Catal. Today 114, 263 (2006)CrossRefGoogle Scholar
  62. 62.
    J. Zhang, P. Jiang, Y. Shen, W. Zhang, X. Li, Microporous Mesoporous Mater. 206, 161 (2015)CrossRefGoogle Scholar
  63. 63.
    G.R. Bardajee, R. Malakooti, I. Abtin, H. Atashin, Microporous Mesoporous Mater. 169, 67 (2013)CrossRefGoogle Scholar
  64. 64.
    R. Malakooti, G.R. Bardajee, S. Hadizadeh, H. Atashin, H. Khanjari, Transit. Metal Chem. 39, 47 (2014)CrossRefGoogle Scholar
  65. 65.
    I.C. Chisem, J. Rafelt, M.T. Shieh, J. Chisem (née Bovey), J.H. Clark, R. Jachuck, D. Macquarrie, C. Ramshaw, K. Scott, Chem. Commun. 18, 1949 (1998)CrossRefGoogle Scholar
  66. 66.
    D. Zhao, J. Feng, Q. Huo, N. Melosh, G.H. Fredrickson, B.F. Chmel ka, G.D. Stucky, Science 273, 548 (1998)CrossRefGoogle Scholar
  67. 67.
    S. Jana, B. Dutta, R. Bera, S. Koner, Langmuir 23, 2492 (2007)CrossRefPubMedGoogle Scholar
  68. 68.
    X. Wang, G. Wu, W. Wei, Y. Sun, Catal. Lett. 136, 96 (2010)CrossRefGoogle Scholar
  69. 69.
    D. Zhao, Q. Huo, J. Feng, B.F. Chmelka, G.D. Stucky, J. Am. Chem. Soc. 120, 6024 (1998)CrossRefGoogle Scholar
  70. 70.
    L. Saikia, D. Srinivas, P. Ratnasamy, Appl. Catal. A Gen. 309, 144 (2006)CrossRefGoogle Scholar
  71. 71.
    Y. Li, B. Yan, H. Yang, J. Phys. Chem. C 112, 3959 (2008)CrossRefGoogle Scholar
  72. 72.
    E.A. Gilandeh, M.A. Hashjin, A. Yahyazadeh, H. Salemid, RSC Adv. 6, 55444 (2016)CrossRefGoogle Scholar
  73. 73.
    K. Niknam, A. Jamali, Chin. J. Catal. 33, 1840 (2012)CrossRefGoogle Scholar
  74. 74.
    Z.K. Jaberi, M.S. Moaddeli, M. Setoodehkhah, M.R. Nazarifar, Res. Chem. Intermed. 42, 4641 (2016)CrossRefGoogle Scholar
  75. 75.
    A. Khazaei, M.A. Zolfigol, F. Karimitabar, I. Nikokar, A.R. Moosavi-Zare, RSC Adv. 5, 71402 (2015)CrossRefGoogle Scholar
  76. 76.
    M.N. Khan, S. Pal, S. Karamthulla, L.H. Choudhury, RSC Adv. 4, 3732 (2014)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of ChemistryUrmia UniversityUrmiaIran
  2. 2.Department ChemistryPayame Noor University (PNU)TehranIran

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