Skip to main content
Log in

A new role for solar energy as a renewable energy source for catalyst-solvent free gram-scale synthesis of pyrano[2,3-d]pyrimidine scaffolds

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

Abstract

In the realm of chemistry, increased energy consumption as a result of population development and industrialisation necessitates the usage of renewable energy sources. Nonrenewable energy sources emit not only greenhouse gases but also other toxic pollutants that harm all living creatures. This clearly necessitates the employment of an ecologically acceptable and cost-effective renewable energy source by the researchers. The Knoevenagel-Michael cyclocondensation of aldehyde derivatives, malononitrile, and barbituric acid/1,3-dimethylbarbituric acid via a three-condensation domino reaction can be used to create pyrano[2,3-d]pyrimidine scaffolds. This study establishes solar energy as a novel renewable energy source for the synthesis of pyrano[2,3-d]pyrimidine scaffolds under catalyst-solvent-free conditions, with excellent yields, reaction time savings, and atom economy. This reaction was carried out on a range of substrates with the use of a renewable energy source (sunlight) and a relatively simple experimental setup. The reaction was extremely fast, and there was no need for a solvent or chromatographic purification. According to a multigram scale reaction of model substrates, this reaction might be scaled up without affecting the outcome. Furthermore, the approach's broad applicability was proved by its usage to synthesis real-world pharmaceutical molecules.

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
Scheme 3
Scheme 4

Similar content being viewed by others

Availability of data and materials

All data generated or analyzed during this study are included in this published article and Supporting Information file.

References

  1. Y.U. Gadkari, N.T. Hatvate, B.S. Takale, V.N. Telvekar, New. J. Chem. 44, 8167 (2020)

    Article  CAS  Google Scholar 

  2. Y.U. Gadkari, N.T. Hatvate, V.N. Telvekar, Sustain. Chem. Pharm. 21, 100444 (2021)

    Article  CAS  Google Scholar 

  3. N. Kitamura, A. Onishi, Eur. Pat, 163599, 1984Chem. Abstr. 104, 186439 (1984)

  4. S. Furuya, T. Ohtaki, Eur. Pat. Appl., EP 608565, 1994 Chem. Abstr. 121, 205395w (1994)

  5. D. Heber, C. Heers, U. Ravens, Pharmazie 48, 537 (1993)

    CAS  PubMed  Google Scholar 

  6. W.J. Coates, Eur. Pat., 351058 Chem. Abstr. 113, 40711 (1990)

  7. Y. Sakuma, M. Hasegawa, K. Kataoka, K. Hoshina, N. Yamazaki, T. Kadota, H. Yamaguchi, WO 91/05785 PCT Int. Appl., 1989 May 2. Chem Abstr. 115, 71646 (1991)

  8. A.D. Broom, J.L. Shim, G.L. Anderson, J. Org. Chem. 41, 1095 (1976)

    Article  CAS  PubMed  Google Scholar 

  9. N. Seyyedi, F. Shirini, M.S. Langarudi, RSC Adv. 6, 44630 (2016)

    Article  CAS  Google Scholar 

  10. M. Bararjanian, S. Balalaie, B. Movassag, A.M. Amani, J. Iran. Chem. Soc. 6, 436 (2009)

    Article  CAS  Google Scholar 

  11. E. Sheihhosseini, T. Sattaei Mokhatari, M. Faryabi, A. Rafiepour, S. Soltaninejad, Iran. J. Chem. Chem. Eng. 35, 43 (2016)

  12. B. Sadeghi, M. Bouslik, A.M. Shishehbore, J. Iran. Chem. Soc. 12, 1801 (2015)

    Article  CAS  Google Scholar 

  13. B. Sabour, M.H. Peyrovi, M. Hajimohammadi, Res. Chem. Intermed. 41, 1343 (2015)

    Article  CAS  Google Scholar 

  14. A. Khazaei, H.A. Nik, A.R. Moosavi-Zare, J. Chin. Chem. Soc. 62, 675 (2015)

    Article  CAS  Google Scholar 

  15. S.N. Maddila, S. Maddila, W.E. van Zyl, S.B. Jonnalagadda, RSC Adv. 5, 37360 (2015)

    Article  CAS  Google Scholar 

  16. A. Maleki, A.A. Jafari, S. Yousefi, Carbohydr. Polym. 175, 409 (2017)

    Article  CAS  PubMed  Google Scholar 

  17. A.R. Bhat, A.H. Shalla, R.S. Dongre, J. Taibah Univ. Sci. 10, 9 (2016)

    Article  Google Scholar 

  18. F. Mohamadpour, Polycycl. Aromat. Compd. 41, 160 (2021)

    Article  CAS  Google Scholar 

  19. M.A. Zolfigol, R. Ayazi-Nasrabadi, S. Baghery, Appl. Organomet. Chem. 30, 273 (2016)

    Article  CAS  Google Scholar 

  20. D. Azarifar, R. Nejat-Yami, F. Sameri, Z. Akrami, Lett. Org. Chem. 9, 435 (2012)

    Article  CAS  Google Scholar 

  21. A. Khazaei, A. Ranjbaran, F. Abbasi, M. Khazaei, A.R. Moosavi-Zare, RSC Adv. 5, 13643 (2015)

    Article  CAS  Google Scholar 

  22. F. Mohamadpour, Polycycl. Aromat. Compd. 42, 2805 (2022)

    Article  CAS  Google Scholar 

  23. J. Albadi, A. Mansournezhad, T. Sadeghi, Res. Chem. Intermed. 41, 8317 (2015)

    Article  CAS  Google Scholar 

  24. J. Yu, H. Wang, Synth. Commun. 35, 3133 (2005)

    Article  CAS  Google Scholar 

  25. M.A. Bodaghifard, M. Solimannejad, S. Asadbegi, S. Dolatabadifarahani, Res. Chem. Intermed. 42, 1165 (2016)

    Article  CAS  Google Scholar 

  26. M.M. Heravi, A. Ghods, K. Bakhtiari, Synth. Commun. 40, 1927 (2010)

    Article  CAS  Google Scholar 

  27. F. Mohamadpour, J. Photochem. Photobiol. A: Chem. 407, 113041 (2021)

    Article  CAS  Google Scholar 

  28. F. Mohamadpour, Monatsh. Chem. 152, 507 (2021)

    Article  CAS  Google Scholar 

  29. B. Borah, M. Patat, V. Singh, M. Sivaprakash, M.S. Prasad, L.R. Chowhan, Org. Biomol. Chem. 21, 1518 (2023)

    Article  CAS  PubMed  Google Scholar 

  30. M.Tavakolian, M. Hosseini-Sarvari, ACS Sustain. Chem. Eng. 9, 4296 (2021)

  31. M. Zhang, M.N. Chen, Z.H. Zhang, Adv. Synth. Catal. 361, 5182 (2019)

    Article  CAS  Google Scholar 

  32. X. Xie, L. Wang, Q. Zhou, Y. Ma, Z.M. Wang, P. Li, Chin. Chem. Lett. 33, 5069 (2022)

    Article  CAS  Google Scholar 

  33. Z. Wang, N. Meng, Y. Lv, W. Wei, H. Yue, G. Zhong, Chin. Chem. Lett. 34, 107599 (2023)

    Article  CAS  Google Scholar 

  34. F. Mohamadpour, Dyes Pigm. 194, 109628 (2021)

    Article  CAS  Google Scholar 

  35. F. Mohamadpour, J. Photochem. Photobiol. A: Chem. 418, 113428 (2021)

    Article  CAS  Google Scholar 

  36. F. Mohamadpour, Sci. Rep. 12, 7253 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. F. Mohamadpour, RSC Adv. 12, 10701 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge financial support from the Research Council of the Apadana Institute of Higher Education.

Funding

The authors received no specific funding for this work.

Author information

Authors and Affiliations

Authors

Contributions

Farzaneh Mohamadpour wrote the main manuscript text and Farzaneh Mohamadpour prepared figures 1-4. Farzaneh Mohamadpour reviewed the manuscript.

Corresponding author

Correspondence to Farzaneh Mohamadpour.

Ethics declarations

Competing interests

There is no conflict of interest to declare.

Ethical Approval

Not applicable.

Consent to participate

Not applicable.

Consent for publication

Not applicable.

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 (PDF 231 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mohamadpour, F. A new role for solar energy as a renewable energy source for catalyst-solvent free gram-scale synthesis of pyrano[2,3-d]pyrimidine scaffolds. Res Chem Intermed 49, 3881–3891 (2023). https://doi.org/10.1007/s11164-023-05057-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-023-05057-9

Keywords

Navigation