Skip to main content
SpringerLink
Log in

Synthesis of pyrano[2,3‐d]pyrimidines and pyrido[2,3‐d]pyrimidines in the magnetized deionized water based on UV–visible study

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

A green synthetic route to the facile one-pot multicomponent synthesis of pyrano[2,3‐d]pyrimidines and pyrido[2,3‐d]pyrimidines have been developed using magnetized deionized water (MDW) as a green solvent under catalyst-free conditions. All reactions carried out in a short period of time and the products are obtained in high-to-excellent yields. The developed synthetic technique offers numerous advantages including eco-friendly, clean synthesis, simplicity, low cost, short reaction times, high reaction yields, and easy workup compared to the traditional synthetic method. Moreover, the reaction rates were followed spectrophotometrically by monitoring the changes in the absorption spectrum of the reaction mixture in ordinary deionized water and MDW.

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
Scheme 2
Scheme 3
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

References

  1. C.J. Li, T.H. Chan, Organic Reaction in Aqueous Media (Wiley, New York, 1997)

    Google Scholar 

  2. V.K. Golovleva, G.E. Dunaevskii, T.L. Levdikova, Y.S. Sarkisov, Y.I. Tsyganok, Russ. Phys. J. 43, 1009 (2000)

    CAS  Google Scholar 

  3. O. Mosin, I. Ignatov, Nanotechnol. Res. Pract. 4, 187 (2014)

    Google Scholar 

  4. I. Mosin, Ignatov. Nanotechnol. Res. Pract. 6, 81 (2015)

    Google Scholar 

  5. J.P. Zhu, H. Bienayme, Multicomponent Reactions (Wiley, Hoboken, 2006)

    Google Scholar 

  6. H. Pellissier, Chem. Rev. 113, 442 (2013)

    CAS  PubMed  Google Scholar 

  7. C.M.R. Volla, I. Atodiresei, M. Rueping, Chem. Rev. 114, 2390 (2014)

    CAS  PubMed  Google Scholar 

  8. P. Chauhan, S. Mahajan, D. Enders, Acc. Chem. Res. 50, 2809 (2017)

    CAS  PubMed  Google Scholar 

  9. A.H. Shamroukh, M.A. Zaki, E.M.H. Morsy, F.M. Abdel-Motti, F.M.E. Abdel-Megeid, Arch. Pharm. Chem. Life Sci. 340, 236 (2007)

    CAS  Google Scholar 

  10. L.R. Bennett, C.J. Blankely, R.W. Fleming, R.D. Smith, D.K. Tessonam, J. Med. Chem. 24, 382 (1981)

    CAS  PubMed  Google Scholar 

  11. K.N. Mohana, B.N.P. Kumar, L. Mallesha, Drug Invent. Today 5, 216 (2013)

    CAS  Google Scholar 

  12. M.S. Mohamed, R. Kamel, S.S. Fatahala, Eur. J. Med. Chem. 45, 2994 (2010)

    CAS  PubMed  Google Scholar 

  13. A.M. Fargualy, N.S. Habib, K.A. Ismail, A.M.M. Hassan, M.T.M. Sarg, Eur. J. Med. Chem. 66, 276 (2013)

    CAS  PubMed  Google Scholar 

  14. F. Herold, J. Kleps, A. Chodkowski, B. Gutkowska, Acta Pol. Pharm. 56, 385 (1999)

    CAS  PubMed  Google Scholar 

  15. T.A. Farghaly, H.M. Hassaneen, Arch. Pharm. Res. 36, 564 (2013)

    CAS  PubMed  Google Scholar 

  16. C. Kurumurthy, S.P. Rao, V.B. Swamy, S.G. Kumar, S.P. Rao, B. Narsaiah, L.R. Velatooru, R. Pamanji, V.J. Rao, Eur. J. Med. Chem. 46, 3462 (2011)

    CAS  PubMed  Google Scholar 

  17. A. Banerjee, M.Y. Pawar, S. Patil, P.S. Yadav, P.A. Kadam, V.G. Kattige, D.S. Deshpande, P.V. Pednekar, M.K. Pisat, L.A. Gharat, Bioorg. Med. Chem. Lett. 24, 4838 (2014)

    CAS  PubMed  Google Scholar 

  18. M.N. Nasr, M.M. Gineinah, Arch. Pharm. (Weinheim) 335, 289 (2002)

    CAS  Google Scholar 

  19. S.P. Satasia, P.N. Kalaria, D.K. Raval, Org. Biomol. Chem. 12, 1751 (2014)

    CAS  PubMed  Google Scholar 

  20. R. Baharfar, R. Azimi, Syn. Commun. 44, 89 (2014)

    CAS  Google Scholar 

  21. Y. He, H. Guo, J. Tian, J. Chem. Res. 35, 528 (2011)

    Google Scholar 

  22. L. Jalili-Baleh, N. Mohammadi, M. Khoobi, L. Maimani, A. Foroumadi, A. Shafiee, Helv. Chim. Acta 96, 1601 (2013)

    CAS  Google Scholar 

  23. G. Brahmachari, B. Banerjee, ACS Sustain. Chem. Eng. 2, 411 (2014)

    CAS  Google Scholar 

  24. G.K. Verma, K. Raghuvanshi, R. Kumar, M.S. Singh, Tetrahedron Lett. 53, 399 (2012)

    CAS  Google Scholar 

  25. A. Rahmati, Z. Khalesi, Chin. Chem. Lett. 23, 1149 (2012)

    CAS  Google Scholar 

  26. S. Abdolmohammadi, M. Afsharpour, Chin. Chem. Lett. 23, 257 (2012)

    CAS  Google Scholar 

  27. X.-S. Wang, Z.-S. Zeng, D.-Q. Shi, S.-J. Tu, X.-Y. Wei, Z.-M. Zong, Synth. Commun. 35, 1921 (2005)

    CAS  Google Scholar 

  28. S. Samai, G. Chandra Nandi, S. Chowdhury, M. Shankar Singh, Tetrahedron 67, 5935 (2011)

    CAS  Google Scholar 

  29. A. Mossafaii Rad, M. Mokhtary, Int. Nano Lett. 5, 109 (2015)

    Google Scholar 

  30. T. Yang, H. He, W. Ang, Y.-H. Yang, J.-Z. Yang, Y.-N. Lin, H.-C. Yang, W.-Y. Pi, Z.-C. Li, Molecules 17, 2351 (2012)

    CAS  PubMed  PubMed Central  Google Scholar 

  31. Y. Wang, L. Zhou, Y. Zhu, M. Zhang, L. Song, H. Deng, J. Fluor. Chem. 200, 162 (2017)

    CAS  Google Scholar 

  32. S. Maddila, K.K. Gangu, S.N. Maddila, S.B. Jonnalagadda, Res. Chem. Intermed. 44, 1397 (2018)

    CAS  Google Scholar 

  33. M. Bakherad, A. Keivanloo, M. Gholizadeh, R. Doosti, M. Javanmardi, Res. Chem. Intermed. 43, 1013 (2017)

    CAS  Google Scholar 

  34. M. Bakherad, R. Doosti, A. Keivanloo, M. Gholizadeh, A.H. Amin, Lett. Org. Chem. 14, 510 (2017)

    CAS  Google Scholar 

  35. M. Bakherad, F. Moosavi, R. Doosti, A. Keivanloo, M. Gholizadeh, New J. Chem. 42, 4559 (2018)

    CAS  Google Scholar 

  36. M. Bakherad, R. Doosti, A. Keivanloo, M. Gholizadeh, K. Jadidi, J. Iran. Chem. Soc. 14, 2591 (2017)

    CAS  Google Scholar 

  37. M. Bakherad, A. Keivanloo, Z. Bakherad, Z. Toozandejani, M. Mahdavi, J. Chin. Chem. Soc. 66, 674 (2019)

    CAS  Google Scholar 

  38. A. Shaabani, S. Samadi, A. Rahmati, Synth. Commun. 37, 491 (2007)

    CAS  Google Scholar 

  39. N. Maleki, Z. Shakarami, S. Jamshidian, M. Nazari, Acta Chem. Iasi 24, 20 (2016)

    Google Scholar 

  40. S. Abdolmohammadi, S. Balalaie, Int. J. Org. Chem. 2, 7 (2012)

    CAS  Google Scholar 

  41. E.J. Toledo, T.C. Ramalho, Z.M. Magriotis, J. Mol. Struct. 888, 409 (2008)

    CAS  Google Scholar 

  42. M. Bakherad, Z. Moosavi-Tekyeh, A. Keivanloo, M. Gholizadeh, Z. Toozandejani, Res. Chem. Intermed. 44, 373 (2018)

    CAS  Google Scholar 

  43. H.M. Lotfy, S.S. Saleh, Spectrochim. Acta A Mol. Biomol. Spectrosc. 205, 160 (2018)

    CAS  PubMed  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge the financial support of the Research Council of the Shahrood University of Technology.

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Shahrood University of Technology, Shahrood, 3619995161, Iran

    Mohammad Bakherad, Ghadamali Bagherian, Amin Rezaeifard, Fatemeh Mosayebi, Behzad Shokoohi & Ali Keivanloo

Authors
  1. Mohammad Bakherad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ghadamali Bagherian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Amin Rezaeifard
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Fatemeh Mosayebi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Behzad Shokoohi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ali Keivanloo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Mohammad Bakherad or Ghadamali Bagherian.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 5274 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bakherad, M., Bagherian, G., Rezaeifard, A. et al. Synthesis of pyrano[2,3‐d]pyrimidines and pyrido[2,3‐d]pyrimidines in the magnetized deionized water based on UV–visible study. J IRAN CHEM SOC 18, 839–852 (2021). https://doi.org/10.1007/s13738-020-02073-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-020-02073-z

Keywords

Search

Navigation