Skip to main content
SpringerLink
Log in

Green synthesis of dihydropyrano[3,2-c]chromene derivatives using amino-terminated PAMAM dendrimer as catalyst

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

Abstract

d-Sorbitol-cored PAMAM dendrimer (SOR-G1) was effectively synthesized by the ring opening polymerization of epichlorohydrin. The dendrimer was characterized using different spectroscopic and analytical techniques including IR and NMR spectroscopy, TG–DTA, and GPC. Dihydropyrano[3,2-c]chromene derivatives were synthesized using SOR-G1 as a catalyst, and it was synthesized within 30 min in ethanol/water medium and excellent yield was obtained. SOR-G1 acted as a good base catalyst on the basis of amine capacity and good thermal stability. The prepared dihydropyrano[3,2-c]chromene derivatives were characterized using GCMS, LCMS, IR, 1H NMR, and 13C NMR spectra. The catalyst could be reused up to three reaction cycles without losing its catalytic activity.

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Scheme 2
Fig. 15
Fig. 16
Fig. 17
Fig. 18
Scheme 3

Similar content being viewed by others

References

  1. B. Maleki, F. Taheri, R. Tayebee, F. Adibian, Org. Prep. Proced. Int. 53, 284 (2021)

    Article  CAS  Google Scholar 

  2. O.V. Kharissova, B.I. Kharisov, C.M. Oliva González, Y.P. Méndez, I. López, R. Soc. Open Sci. 6, 191378 (2019)

    Article  Google Scholar 

  3. D. Rajguru, B.S. Keshwal, S. Jain, Med. Chem. Res. 22, 5934 (2013)

    Article  CAS  Google Scholar 

  4. N. Menges, Green Chem. 5, 74, (2017).

  5. F. Adibian, A.R. Pourali, B. Maleki, M. Baghayeri, A. Amiri, Polyhedron 175, 114179 (2020)

    Article  Google Scholar 

  6. R. Ghorbani-Vaghei, Z. Toghraei-Semiromi, R. Karimi-Nami, J. Braz. Chem. Soc. 22, 905 (2011)

    CAS  Google Scholar 

  7. A. M. El-Agrody, A. M. Fouda, M. A. Assiri, A. Mora, T. E. Ali, M. M. Alam, and M. Y. Alfaifi, Med. Chem. Res. 1, 29, 617–629, (2020).

  8. S.S. Mansoor, K. Logaiya, K. Aswin, P.N. Sudhan, J. Taibah Univ. Sci. 9, 213 (2015)

    Article  Google Scholar 

  9. D.C. Mungra, M.P. Patel, D.P. Rajani, R.G. Patel, Eur. J. Med. Chem. 46, 4192 (2011)

    Article  CAS  Google Scholar 

  10. S. Jain, P.K. Paliwal, G.N. Babu, A. Bhatewara, J. Saudi Chem. Soc. 18, 535 (2014)

    Article  CAS  Google Scholar 

  11. D.S. Patel, J.R. Avalani, D.K. Raval, J. Saudi Chem. Soc. 20, S401 (2016)

    Article  CAS  Google Scholar 

  12. M. Khoobi, M. Alipour, A. Sakhteman, H. Nadri, A. Moradi, M. Ghandi, S. Emami, A. Foroumadi, A. Shafiee, Eur. J. Med. Chem. 68, 260 (2013)

    Article  CAS  Google Scholar 

  13. E. Mollashahi, M. Nikraftar, J. Saudi Chem. Soc. 22, 42 (2018)

    Article  CAS  Google Scholar 

  14. S. Kanakaraju, B. Prasanna, S. Basavoju, G.V.P. Chandramouli, Arab. J. Chem. 10, S2705 (2017)

    Article  CAS  Google Scholar 

  15. A.M. Abdella, M.F. Mohamed, A.F. Mohamed, A.H.M. Elwahy, I.A. Abdelhamid, J. Heterocycl. Chem. 55, 498 (2018)

    Article  CAS  Google Scholar 

  16. N.N. Pesyan, G.R. Bardajee, E. Kashani, M. Mohammadi, H. Batmani, Res. Chem. Intermed. 46, 347 (2020)

    Article  Google Scholar 

  17. G. J. Safaei, F. Eshteghal, and M. A. L. I. Ghasemzadeh, Acta Chim Slov. 61, 703, (2014).

  18. J. Balou, M.A. Khalilzadeh, D. Zareyee, Sci. Rep. 9, 1 (2019)

    Article  CAS  Google Scholar 

  19. K. Tabatabaeian, H. Heidari, M. Mamaghani, N.O. Mahmoodi, Appl. Organomet. Chem. 26, 56 (2012)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  21. E. Abbaspour-Gilandeh, S.C. Azimi, K. Rad-Moghadam, A. Mohammadi-Barkchai, Iran. J. Catal. 3, 91 (2013)

    CAS  Google Scholar 

  22. M.M. Heravi, B.A. Jani, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Catal. Commun. 10, 272 (2008)

    Article  CAS  Google Scholar 

  23. A. Ghorbani-Choghamarani, M. Mohammadi, L. Shiri, Z. Taherinia, Res. Chem. Intermed. 45, 5705 (2019)

    Article  CAS  Google Scholar 

  24. J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)

    Article  CAS  Google Scholar 

  25. J.M. Khurana, B. Nand, P. Saluja, Tetrahedron 66, 5637 (2010)

    Article  CAS  Google Scholar 

  26. B. Maleki, Org. Prep. Proced. Int. 48, 303 (2016)

    Article  CAS  Google Scholar 

  27. A. Kokel, C. Schäfer, B. Török, Curr. Org. Synth. 16, 615 (2019)

    Article  CAS  Google Scholar 

  28. R.K.G. Panicker, S. Krishnapillai, Tetrahedron Lett. 55, 2352 (2014)

    Article  Google Scholar 

  29. D. Astruc, F. Chardac, Chem. Rev. 101, 2991 (2001)

    Article  CAS  Google Scholar 

  30. I. Morao, F.P. Cossío, Tetrahedron Lett. 38, 6461 (1997)

    Article  CAS  Google Scholar 

  31. V.A. Osyanin, D.V. Osipov, Y.N. Klimochkin, Tetrahedron 68, 5612 (2012)

    Article  CAS  Google Scholar 

  32. L. Khazdooz, A. Zarei, T. Ahmadi, H. Aghaei, N. Nazempour, L. Golestanifar, N. Sheikhan, React. Kinet. Mech. Catal. 122, 229 (2017)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors express their gratitude to UGC, New Delhi, for financial assistance under SAP DRS III and KSCSTE, Government of Kerala, for providing a JRF to Unnikrishnan V.

Author information

Author notes

  1. V. Unnikrishnan, G. Avudaiappan, Kiran James & M. R. Palmurukan

    Present address: Department of Applied Chemistry, Cochin University of Science and Technology, Kochi, India

Authors and Affiliations

  1. Department of Applied Chemistry, Cochin University of Science and Technology, Kochi, India

    K. Sreekumar

Authors
  1. V. Unnikrishnan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. Avudaiappan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kiran James
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. R. Palmurukan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. K. Sreekumar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to K. Sreekumar.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOC 4711 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Unnikrishnan, V., Avudaiappan, G., James, K. et al. Green synthesis of dihydropyrano[3,2-c]chromene derivatives using amino-terminated PAMAM dendrimer as catalyst. Res Chem Intermed 48, 379–399 (2022). https://doi.org/10.1007/s11164-021-04590-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-021-04590-9

Keywords

Search

Navigation