SpringerLink
Log in

An eco-friendly and magnetized biopolymer cellulose-based heterogeneous acid catalyst for facile synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A cellulose-based magnetic nano-composite supported SO3H group was synthesized and characterized using Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, X-ray diffraction, and scanning electron microscopy. Thereafter, its capability to promote the one-pot, three-component synthesis of pyrimido [4,5-b] quinolone and pyrido [2,3-d] pyrimidine derivatives was evaluated. The obtained results are indicative of excellent yields and short reaction times. The biopolymer based catalyst is readily recovered and reused several times without a decrease in yield.

Graphical Abstract

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

Access this article

Log in via an institution

Price includes VAT (United Kingdom)

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 3
Scheme 4
Scheme 5
Fig. 7

Similar content being viewed by others

References

  1. J. Safari, S. Gandomi-Ravandi, Z. Akbari, J. Adv. Res. 4, 6 (2013)

    Article  Google Scholar 

  2. I.R. Siddiqui, P. Rai, R. Rahila, H. Sagir, P. Singh, RSC Adv. 5, 35 (2015)

    Google Scholar 

  3. R.M. Singh, N. Sharma, R. Kumar, M. Asthana, S. Upadhyay, Tetrahedron Lett. 68, 50 (2012)

    Google Scholar 

  4. J.M. Khurana, A. Chaudhary, B. Nand, A. Lumb, Tetrahedron Lett. 53, 24 (2012)

    Article  Google Scholar 

  5. I. Devi, B.S.D. Kumar, P.J. Bhuyan, Tetrahedron Lett. 44, 45 (2003)

    Article  Google Scholar 

  6. N.A. Hassan, M.I. Hegab, F.M. Abdel-Motti, S.H.A. Hebah, F.M.E. Abdel-Megeid, A.I. Hashem, J. Heterocycl. Chem. 44, 4 (2007)

    Google Scholar 

  7. A. Shaabani, Z. Hezarkhani, M.T. Faroghi, Monatsh. Chem. (2016). doi:10.1007/s00706-016-1717-7

    Google Scholar 

  8. M. Shamsi-Sani, F. Shirini, M. Abedini, M. Seddighi, Res. Chem. Intermed. 42, 2 (2016)

    Article  Google Scholar 

  9. E. Kolvari, N. Koukabi, M.M. Hosseini, J. Mol. Catal. A: Chem. 397, 68 (2015)

    Article  CAS  Google Scholar 

  10. A.R. Kiasat, L. Hemat-Alian, Res. Chem. Intermed. 41, 2 (2015)

    Google Scholar 

  11. M. Wu, Y. Wang, D. Wang, M. Tan, P. Li, W. Wu, N. Tsubaki, J. Porous Mater. 23, 1 (2016)

    Article  Google Scholar 

  12. B. Sadeghi, M.H. Sowlat Tafti, J. Iran. Chem. Soc. 13, 8 (2016)

    Google Scholar 

  13. M.A. Zolfigol, Tetrahedron 57, 46 (2001)

    Google Scholar 

  14. F. Nemati, M.M. Heravi, R. Saeedi Rad, Chin. J. Catal. 33, 11–12 (2012)

    Article  Google Scholar 

  15. E. Mehrasbi, Y. Sarrafi, A. Vahid, H. Alinezhad, Res. Chem. Intermed. 41, 7 (2015)

    Google Scholar 

  16. S. Mahdudi, D. Saberi, A. Heydari, J. Iran. Chem. Soc. 12, 5 (2015)

    Article  Google Scholar 

  17. A. Amoozadeh, S. Golian, S. Rahmani, RSC Adv. 5, 57 (2015)

    Article  Google Scholar 

  18. A. Amoozadeh, S. Rahmani, J. Mol. Catal. A: Chem. 396, 96–107 (2015)

    Article  CAS  Google Scholar 

  19. E. Kolvari, N. Koukabi, M.M. Hosseini, M. Vahidian, E. Ghobadi, RSC Adv. 6, 9 (2016)

    Google Scholar 

  20. F. Nemati, A. Elhampour, M.B. Natanzi, S. Sabaqian, J. Iran. Chem. Soc. 13, 6 (2016)

    Article  Google Scholar 

  21. R.H. Vekariya, H.D. Patel, RSC Adv. 5, 61 (2015)

    Google Scholar 

  22. A.M. Salgueiro, A.L. Daniel-da-Silva, A.V. Girão, P.C. Pinheiro, T. Trindade, Chem. Eng. J. 229, 276–284 (2013)

    Article  CAS  Google Scholar 

  23. C. Esmaeili, M. Ghasemi, L.Y. Heng, S.H.A. Hassan, M.M. Abdi, W.R.W. Daud, H. Ilbeygi, A.F. Ismail, Carbohydr. Polym. 114, 253–259 (2014)

    Article  CAS  Google Scholar 

  24. S. Rostamnia, B. Zeynizadeh, E. Doustkhah, A. Baghban, K.O. Aghbash, Catal. Commun. 68, 77–83 (2015)

    Article  CAS  Google Scholar 

  25. Y. Habibi, L.A. Lucia, O.J. Rojas, Chem. Rev. 110, 6 (2010)

    Article  Google Scholar 

  26. C. Johansson, J. Bras, I. Mondragon, P. Nechita, D. Plackett, P. Simon, D.G. Svetec, S. Virtanen, M.G. Baschetti, C. Breen, Bioresources. 7, 2 (2012)

    Article  Google Scholar 

  27. Z. Ghasemi, S. Shojaei, A. Shahrisa, RSC Adv. 6, 61 (2016)

    Article  Google Scholar 

  28. A. Shaabani, H. Nosrati, M. Seyyedhamzeh, Res. Chem. Intermed. 41, 6 (2015)

    Google Scholar 

  29. L. Edjlali, R.H. Khanamiri, J. Abolhasani Monatsh. Chem. 146, 8 (2015)

    Google Scholar 

  30. B. Liu, Z. Zhang, K. Huang, Cellulose 20, 4 (2013)

    Google Scholar 

  31. H.R. Shaterian, F. Rigi, Res. Chem. Intermed. 40, 5 (2014)

    Google Scholar 

  32. A. Shaabani, A. Rahmati, Z. Badri, Catal. Commun. 9, 1 (2008)

    Article  Google Scholar 

  33. R.H. Vekariya, H.D. Patel, ARKIVOC 1, 136–159 (2015)

    Google Scholar 

  34. R.K. Sharma, S. Dutta, S. Sharma, R. Zboril, R.S. Varma, M.B. Gawande, Green Chem. 18, 11 (2016)

    Article  Google Scholar 

  35. B. Liu, Z. Zhang, ACS Catal. 6, 326 (2016)

    Article  CAS  Google Scholar 

  36. B. Liu, Y. Ren, Z. Zhang, Green Chem. 17, 1610 (2015)

    Article  CAS  Google Scholar 

  37. Z. Zhang, J. Zhen, B. Liu, K. Lv, K. Deng, Green Chem. 17, 1308 (2015)

    Article  CAS  Google Scholar 

  38. Sh Yin, J. Sun, B. Liu, Z. Zhang, J. Mater. Chem. A 3, 4992 (2015)

    Article  CAS  Google Scholar 

  39. Z. Zhang, Z. Yuan, D. Tang, Y. Ren, K. Lv, B. Liu, Chem. Sus. Chem. 7, 3496 (2014)

    Article  CAS  Google Scholar 

  40. N. Mei, B. Liu, J. Zheng, K. Lv, D. Tang, Z. Zhang, Catal. Sci. Technol. 5, 3194 (2015)

    CAS  Google Scholar 

  41. F. Nemati, A. Elhampour, H. Farrokhi, M. Bagheri, Natanzi. Catal. Commun. 66, 15 (2015)

    Article  CAS  Google Scholar 

  42. F. Nemati, M.M. Heravi, A. Elhampour, RSC Adv. 5, 57 (2015)

    Article  Google Scholar 

  43. F. Nemati, S.H. Nikkhah, A. Elhampour, Chin. Chem. Lett. 26, 11 (2015)

    Article  Google Scholar 

  44. F. Nemati, A.G.G. Ghiyaei, B. Notash, M.H. Shayegan, V. Amani, Tetrahedron Lett. 55, 25 (2014)

    Article  Google Scholar 

  45. F. Nemati, A. Elhampour, S. Zulfaghari, Phosphorus, Sulfur Silicon Relat. Elem. 190, 10 (2015)

    Article  Google Scholar 

  46. F. Nemati, A. Elhampour, Res. Chem. Intermed. 42, 7611 (2016)

    Article  CAS  Google Scholar 

  47. A. Elhampour, F. Nemati, M. Kaveh, Chem. Lett. 45, 223 (2016)

    Article  CAS  Google Scholar 

  48. A. Elhampour, F. Nemati, J. Chin. Chem. Soc. 63, 653 (2016)

    Article  CAS  Google Scholar 

  49. L.C. Fidale, M. Nikolajski, T. Rudolph, S. Dutz, F.H. Schacher, T. Heinze, J. Colloid Interface Sci. 390, 1 (2013)

    Article  Google Scholar 

  50. M.H. Beyki, M. Bayat, S. Miri, F. Shemirani, H. Alijani, Ind. Eng. Chem. Res. 53, 39 (2014)

    Article  Google Scholar 

  51. X. Sun, L. Yang, Q. Li, J. Zhao, X. Li, X. Wang, H. Liu, Chem. Eng. J. 241, 174–183 (2014)

    Google Scholar 

  52. P.V. Chavan, K.S. Pandit, U.V. Desai, M.A. Kulkarni, P.P. Wadgaonkar, RSC Adv. 4, 79 (2014)

    Google Scholar 

  53. H.R. Shaterian, M. Ghashang, M. Feyzi, Appl. Catal. A 345, 2 (2008)

    Article  Google Scholar 

  54. S. Peng, H. Meng, Y. Ouyang, J. Chang, Ind. Eng. Chem. Res. 53, 6 (2014)

    Google Scholar 

  55. H.M. Savanur, R.G. Kalkhambkar, G. Aridoss, K.K. Laali, Tetrahedron Lett. 57, 3029 (2016)

    Article  CAS  Google Scholar 

  56. J.H. Clark, D.J. Macquarrie, J. Sherwood, Chem. Eur. J. 19, 5174 (2013)

    Article  CAS  Google Scholar 

  57. F. Nemati, R. Saeedirad, Chin. Chem. Lett. 24, 5 (2013)

    Article  Google Scholar 

  58. K. Tabatabaeian, A.F. Shojaei, F. Shirini, S.Z. Hejazi, M. Rassa, Chin. Chem. Lett. 25, 2 (2014)

    Article  Google Scholar 

  59. S.-J. Ji, S.-N. Ni, F. Yang, J.-W. Shi, G.-L. Dou, X.-Y. Li, X.-S. Wang, D.-Q. Shi, J. Heterocycl. Chem. 45, 3 (2008)

    Article  Google Scholar 

  60. G.K. Verma, K. Raghuvanshi, R. Kumar, M.S. Singh, Tetrahedron Lett. 53, 4 (2012)

    Google Scholar 

  61. K. Mohammadi, F. Shirini, A. Yahyazadeh, RSC Adv. 5, 23586 (2015)

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors gratefully acknowledge Semnan University Research Council for financial support of this work.

Author information

Authors and Affiliations

  1. Department of Chemistry, Semnan University, Semnan, Iran

    Fatemeh Osanlou, Firouzeh Nemati & Samaneh Sabaqian

Authors
  1. Fatemeh Osanlou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Firouzeh Nemati
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Samaneh Sabaqian
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Firouzeh Nemati.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Osanlou, F., Nemati, F. & Sabaqian, S. An eco-friendly and magnetized biopolymer cellulose-based heterogeneous acid catalyst for facile synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water. Res Chem Intermed 43, 2159–2174 (2017). https://doi.org/10.1007/s11164-016-2752-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2752-z

Keywords

Search

Navigation