Skip to main content
Log in

Poly N,N-dimethylaniline-formaldehyde supported on silica-coated magnetic nanoparticles: a novel and retrievable catalyst for green synthesis of 2-amino-3-cyanopyridines

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

Abstract

Preparation and application of novel and reusable magnetic nanoparticles with poly N,N-dimethylaniline-formaldehyde support as a heterogeneous basic catalyst have been described. The reported catalyst was characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, X-ray diffraction patterns, transmission electron microscopy, energy dispersive X-ray spectroscopy, thermogravimetric analysis and vibrating sample magnetometry. The catalytic performance of this organic-inorganic hybrid nanomaterial has been studied for the green synthesis of 2-amino-3-cyanopyridine derivatives through one-pot four-component reactions. An eco-friendly method, short reaction time, high yield and easy work-up procedure are the advantages of this new methodology over earlier ones.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 3
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. V. Polshettiwar, R.S. Varma, Pure Appl. Chem. 80, 777 (2008)

    CAS  Google Scholar 

  2. J. Tang, L. Wang, Y. Yao, L. Zhang, W. Wang, Tetrahedron Lett. 52, 509 (2011)

    CAS  Google Scholar 

  3. N.M. Evdokimov, A.S. Kireev, A.A. Yakovenko, M.Y. Antipin, I.V. Magedov, A. Kornienko, J. Org. Chem. 72, 3443 (2007)

    CAS  PubMed  Google Scholar 

  4. T. Šmejkal, B. Breit, Angew. Chem. 120, 317 (2008)

    Google Scholar 

  5. R. Makiura, S. Motoyama, Y. Umemura, H. Yamanaka, O. Sakata, H. Kitagawa, Nat. Mater. 9, 565 (2010)

    CAS  PubMed  Google Scholar 

  6. D. Bora, B. Deb, A.L. Fuller, A.M. Slawin, J.D. Woollins, D.K. Dutta, Inorg. Chim. Acta 363, 1539 (2010)

    CAS  Google Scholar 

  7. N. De Rycke, F. Couty, O.R. David, Chem. Eur. J. 17, 12852 (2011)

    PubMed  Google Scholar 

  8. L. Jayasinghe, C.P. Jayasooriya, N. Hara, Y. Fujimoto, Tetrahedron Lett. 44, 8769 (2003)

    CAS  Google Scholar 

  9. C. Temple Jr., G.A. Rener, W.R. Waud, P.E. Noker, J. Med. Chem. 35, 3686 (1992)

    CAS  PubMed  Google Scholar 

  10. S.G. Konda, V. Khedkar, B. Dawane, J. Chem. Pharm. Res. 2, 187 (2010)

    CAS  Google Scholar 

  11. A.E.G. Hammam, N.A.A. El-hafeza, W.H. Midurab, M. Mikołajczyk, Z. Naturforsch. Pt. B 55, 417 (2000)

    Google Scholar 

  12. D.C. Mungra, M.P. Patel, R.G. Patel, Arkivoc 14, 64 (2009)

    Google Scholar 

  13. A.R. Gholap, K.S. Toti, F. Shirazi, R. Kumari, M.K. Bhat, M.V. Deshpande, K.V. Srinivasan, Bioorg. Med. Chem. Lett. 15, 6705 (2007)

    CAS  Google Scholar 

  14. T. Murata, M. Shimada, S. Sakakibara, T. Yoshino, T. Masuda, T. Shintani, H. Sato, Y. Koriyama, K. Fukushima, N. Nunami, Bioorg. Med. Chem. Lett. 14, 4019 (2004)

    CAS  PubMed  Google Scholar 

  15. F. Zhang, Y. Zhao, L. Sun, L. Ding, Y. Gu, P. Gong, Eur. J. Med. Chem. 46, 3149 (2011)

    CAS  PubMed  Google Scholar 

  16. J. Deng, T. Sanchez, L.Q. Al-Mawsawi, R. Dayam, R.A. Yunes, A. Garofalo, M.B. Bolger, N. Neamati, Bioorg. Med. Chem. Lett. 15, 4985 (2007)

    CAS  Google Scholar 

  17. T. Murata, M. Shimada, S. Sakakibara, T. Yoshino, H. Kadono, T. Masuda, M. Shimazaki, T. Shintani, K. Fuchikami, K. Sakai, Bioorg. Med. Chem. Lett. 13, 913 (2003)

    CAS  PubMed  Google Scholar 

  18. A. Girgis, A. Kalmouch, H. Hosni, Amino Acids 26, 139 (2004)

    CAS  PubMed  Google Scholar 

  19. M.A. Bodaghifard, M. Solimannejad, S. Asadbegi, S. Dolatabadifarahani, Res. Chem. Intermed. 42, 1165 (2015)

    Google Scholar 

  20. R. Galeeva, E. Rudometova, M.Y. Gavrilov, V. Kolla, M. Kon’shin, F.Y. Nazmetdinov, Pharm. Chem. J. 31, 89 (1997)

    Google Scholar 

  21. A. Sakurai, H. Midorikawa, Bull. Chem. Soc. Jpn 41, 430 (1968)

    CAS  Google Scholar 

  22. S. Kambe, K. Saito, A. Sakurai, H. Midorikawa, Synthesis 1980, 366 (1980)

    Google Scholar 

  23. A. Mobinikhaledi, S. Asadbegi, M.A. Bodaghifard, Synth. Commun. 19, 1605 (2016)

    Google Scholar 

  24. S. Kankala, R. Pagadala, S. Maddila, C.S. Vasam, S.B. Jonnalagadda, RSC Adv. 5, 105446 (2015)

    CAS  Google Scholar 

  25. B. Maleki, S. Sheikh, Org. Prep. Proced. Int. 47, 368 (2015)

    CAS  Google Scholar 

  26. M.M. Heravi, S.Y.S. Beheshtiha, M. Dehghani, N. Hosseintash, J. Iran. Chem. Soc. 12, 2075 (2015)

    CAS  Google Scholar 

  27. D. Khalili, Tetrahedron Lett. 57, 1721 (2016)

    CAS  Google Scholar 

  28. M. Álvarez-Pérez, J. Marco-Contelles, Arkivoc 2, 283 (2011)

    Google Scholar 

  29. F. Shi, S. Tu, F. Fang, T. Li, Arkivoc 1, 137 (2005)

    Google Scholar 

  30. T.R. Reddy, G.R. Reddy, L.S. Reddy, S. Jammula, Y. Lingappa, R. Kapavarapu, C.L.T. Meda, K.V. Parsa, M. Pal, Eur. J. Med. Chem. 48, 265 (2012)

    Google Scholar 

  31. R. Swathi, K. Sebastian, Resonance 13, 548 (2008)

    CAS  Google Scholar 

  32. S. Roy, K.K. Senapati, P. Phukan, Res. Chem. Intermed. 41, 5753 (2015)

    CAS  Google Scholar 

  33. W. Zhou, J. Yi, J. Lin, S. Fang, X. Peng, Res. Chem. Intermed. 43, 3651 (2017)

    CAS  Google Scholar 

  34. V. Polshettiwar, T. Asefa, G. Hutchings, Nanocatalysis: Synthesis and Applications (Wiley, New York, 2013)

    Google Scholar 

  35. J. Dobson, Drug Dev. Res. 67, 55 (2006)

    CAS  Google Scholar 

  36. Q.A. Pankhurst, J. Connolly, S.K. Jones, J. Dobson, J. Phys. D Appl. Phys. 36, R167 (2003)

    CAS  Google Scholar 

  37. M.M. Khodaei, A. Alizadeh, M. Haghipour, Res. Chem. Intermed. (2017). https://doi.org/10.1007/s11164-017-3008-2

    Article  Google Scholar 

  38. S. Sun, H. Zeng, J. Am. Chem. Soc. 124, 8204 (2002)

    CAS  PubMed  Google Scholar 

  39. M.A. Zolfigol, R. Ayazi-Nasrabadi, RSC Adv. 6, 69595 (2016)

    CAS  Google Scholar 

  40. B. Zakerinasab, M. Nasseri, H. Hassani, M. Samieadel, Res. Chem. Intermed. 42, 3169 (2016)

    CAS  Google Scholar 

  41. Y. Lu, Y. Yin, B.T. Mayers, Y. Xia, Nano Lett. 2, 183 (2002)

    CAS  Google Scholar 

  42. W. Wu, Q. He, C. Jiang, Nanoscale Res. Lett. 3, 397 (2008)

    CAS  PubMed  PubMed Central  Google Scholar 

  43. M. Butterworth, L. Illum, S. Davis, Colloid Surf. A 179, 93 (2001)

    CAS  Google Scholar 

  44. S. Santra, R. Tapec, N. Theodoropoulou, J. Dobson, A. Hebard, W. Tan, Langmuir 17, 2900 (2001)

    CAS  Google Scholar 

  45. M. Pramanik, A. Bhaumik, ACS Appl. Mater. Interfaces. 6, 933 (2014)

    CAS  PubMed  Google Scholar 

  46. M.A. Bodaghifard, A. Mobinikhaledi, S. Asadbegi, Appl. Organomet. Chem. 31, e3557 (2016)

    Google Scholar 

  47. M.A. Bodaghifard, S. Asadbegi, Z. Bahrami, J. Iran. Chem. Soc. 14, 365 (2016)

    Google Scholar 

  48. M.A. Bodaghifard, Z. Faraki, A.R. Karimi, Curr. Org. Chem. 20, 1648 (2016)

    CAS  Google Scholar 

  49. G. Feng, D. Hu, L. Yang, Y. Cui, X.-A. Cui, H. Li, Sep. Purif. Technol. 74, 253 (2010)

    CAS  Google Scholar 

  50. K. Petcharoen, A. Sirivat, Mater. Sci. Eng., B 177, 421 (2012)

    CAS  Google Scholar 

  51. Y. Wan, R. Yuan, F.-R. Zhang, L.-L. Pang, R. Ma, C.-H. Yue, W. Lin, W. Yin, R.-C. Bo, H. Wu, Synth. Commun. 41, 2997 (2011)

    CAS  Google Scholar 

  52. O. El-Salam, D. Ella, N. Ismail, M. Abdullah, Pharmazie 64, 147 (2009)

    Google Scholar 

  53. R. Pagadala, S. Maddila, S. Jonnalagadda, J. Heterocycl. Chem. 52, 1226 (2015)

    CAS  Google Scholar 

  54. R. Khalifeh, M. Ghamari, J. Braz. Chem. Soc. 27, 759 (2016)

    CAS  Google Scholar 

  55. S. Khaksar, M. Yaghoobi, J. Fluor. Chem. 142, 41 (2012)

    CAS  Google Scholar 

  56. Q. Wu, Y. Zhang, S. Cui, Org. Lett. 16, 1350 (2014)

    CAS  PubMed  Google Scholar 

  57. M.A. Zolfigol, M. Kiafar, M. Yarie, A.A. Taherpour, M. Saeidi-Rad, RSC Adv. 6, 50100 (2016)

    CAS  Google Scholar 

  58. R. Pagadala, S. Maddila, V. Moodley, W.E. van Zyl, S.B. Jonnalagadda, Tetrahedron Lett. 55, 4006 (2014)

    CAS  Google Scholar 

  59. K. Can, M. Ozmen, M. Ersoz, Colloid Surf. B 71, 154 (2009)

    CAS  Google Scholar 

  60. W. Stöber, A. Fink, E. Bohn, J. Colloid Interface Sci. 26, 62 (1968)

    Google Scholar 

  61. T. Zeng, L. Yang, R. Hudson, G. Song, A.R. Moores, C.-J. Li, Org. Lett. 13, 442 (2010)

    PubMed  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the financial support of this work by the research council of Arak University.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mohammad Ali Bodaghifard.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 4010 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Asadbegi, S., Bodaghifard, M.A. & Mobinikhaledi, A. Poly N,N-dimethylaniline-formaldehyde supported on silica-coated magnetic nanoparticles: a novel and retrievable catalyst for green synthesis of 2-amino-3-cyanopyridines. Res Chem Intermed 46, 1629–1643 (2020). https://doi.org/10.1007/s11164-017-3200-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-017-3200-4

Keywords

Navigation