SpringerLink
Log in

A facile and efficient synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[4,3-b]pyrans derivatives using phosphate fertilizers MAP, DAP, and TSP as heterogeneous catalysts

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

Abstract

A simple and efficient one-pot synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[4,3-b]pyrans derivatives was described. These reactions were realized through a three-component condensation of aromatic aldehyde, malononitrile, and 5,5-dimethyl-1,3-cyclohexanedione or 4-hydroxy-6-methylpyran-2-one using phosphate fertilizers monoammonium phosphate, NH4(H2PO4)2, (MAP), diammonium phosphate, (NH4)2(HPO4), (DAP), and triple superphosphate, Ca(H2PO4)2.H2O, (TSP) as heterogeneous catalysts. Under optimal reaction conditions, these fertilizers show an excellent catalytic activity. Indeed, the tetrahydrobenzo[b]pyrans and dihydropyrano[4,3-b]pyrans derivatives were obtained with good yields in short reaction times. Also, these fertilizers can be reused at least four times without significant loss of their catalytic activity. Therefore, their application can be contributing to the development of green chemistry.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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
Scheme 2
Fig. 4
Fig. 5
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. D. Rodríguez-Padrón, A.R. Puente-Santiago, A.M. Balu, M.J. Muñoz-Batista, R. Luque, Chem. Cat. Chem. 11, 18 (2019)

    Google Scholar 

  2. S. Bhaskaruni, S. Maddila, W. van Zyl, S. Jonnalagadda, Molecules 23, 1648 (2018)

    Article  PubMed Central  CAS  Google Scholar 

  3. V.S. Konkala, P.K. Dubey, Chin. Chem. Lett. 28, 1571 (2017)

    Article  CAS  Google Scholar 

  4. S.A. Jehbez, H.R. Safaei, J. Iran. Chem. Soc. 15, 1041 (2018)

    Article  CAS  Google Scholar 

  5. G.H. Sayed, M.E. Azab, K.E. Anwer, J. Heterocycl. Chem. 56, 2121 (2019)

    Article  CAS  Google Scholar 

  6. P. Nazari, A. Bazi, S.A. Ayatollahi, H. Dolati, S.M. Mahdavi, L. Rafighdoost, M. Amirmostofian, Iran. J. Pharm. Res. 16, 943 (2017)

    CAS  PubMed  PubMed Central  Google Scholar 

  7. D. Kumar, P. Sharma, H. Singh, K. Nepali, G.K. Gupta, S.K. Jain, F. Ntie-Kang, RSC Adv. 7, 36977 (2017)

    Article  CAS  Google Scholar 

  8. Z. Tashrifi, M. Mohammadi-Khanaposhtani, H. Hamedifar, B. Larijani, S. Ansari, M. Mahdavi, Mol. Divers. 1, 47 (2019)

    Google Scholar 

  9. M. Amirnejad, M.R. Naimi-Jamal, H. Tourani, H. Ghafuri, Monatsh Chem. 144, 1219 (2013)

    Article  CAS  Google Scholar 

  10. S. Rostamnia, A. Morsali, Inorganica Chim. Acta 411, 113 (2014)

    Article  CAS  Google Scholar 

  11. V.M. Joshi, R.L. Magar, P.B. Throat, S.U. Tekale, B.R. Patil, M.P. Kale, R.P. Pawar, Chin. Chem. Lett. 25, 455 (2014)

    Article  CAS  Google Scholar 

  12. S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, P. Salehi, Synth. Commun. 37, 1097 (2007)

    Article  CAS  Google Scholar 

  13. B. Maleki, N. Nasiri, R. Tayebee, A. Khojastehnezhad, H.A. Akhlaghi, RSC Adv. 6, 79128 (2016)

    Article  CAS  Google Scholar 

  14. S.F. Hojati, A. Amiri, N. MoeiniEghbali, S. Mohamadi, Appl Organometal Chem 32, e4235 (2018)

    Article  CAS  Google Scholar 

  15. H. Naeimi, M.F. Zarabi, Res. Chem. Intermed. 44, 3227 (2018)

    Article  CAS  Google Scholar 

  16. A.V. Borhade, J.A. Agashe, D.R. Tope, Russ. J. Appl. Chem. 90, 1005 (2017)

    Article  CAS  Google Scholar 

  17. H.R. Saadati-Moshtaghin, F.M. Zonoz, Mater. Chem. Phys. 199, 159 (2017)

    Article  CAS  Google Scholar 

  18. E. Stoyanov, I. Ivanov, D. Heber, Mol. 5, 19 (2000)

    Article  CAS  Google Scholar 

  19. N.G. Khaligh, Chin. Chem. Lett. 26, 26 (2015)

    Article  CAS  Google Scholar 

  20. M.A. Zolfigol, M. Yarie, S. Baghery, A. Khoshnood, D.A. Alonso, Res. Chem. Intermed. 43, 3291 (2017)

    Article  CAS  Google Scholar 

  21. M. Abaszadeh, M. Seifi, Acta Chem. Iasi 25, 38 (2017)

    Article  Google Scholar 

  22. N.G. Khaligh, S.B.A. Hamid, S.J.J. Titinchi, Polycycl. Aromat. Comp. 37, 31 (2017)

    Article  CAS  Google Scholar 

  23. A. Zarei, M. Yarie, M.A. Zolfigol, K. Niknam, J. Chin. Chem. Soc. 67, 1120 (2019)

  24. A.R. Kiasat, S. Hamid, S.J. Saghanezhad, Nanochem. Res. 1, 157 (2016)

    CAS  Google Scholar 

  25. N.D. Vala, H.H. Jardosh, M.P. Patel, Chinese Chem. Lett. 27, 168 (2016)

    Article  CAS  Google Scholar 

  26. I. Bahammou, A. Esaady, S. Boukhris, R. Ghailane, N. Habbadi, A. Hassikou, A. Souizi, Med. J. Chem. 5, 61 (2016)

    Google Scholar 

  27. S. Chehab, Y. Merroun, T. Ghailane, R. Ghailane, S. Boukhris, A. Souizi, J. Turk. Chem. Soc. Sect A Chem. 5, 355 (2018)

    CAS  Google Scholar 

  28. Y. Merroun, S. Chehab, T. Ghailane, S. Boukhris, R. Ghailane, N. Habbadi, A. Hassikou, B. Lakhrissi, A. Souizi, J. Turk. Chem. Soc. Sect A Chem. 5, 303 (2018)

    Google Scholar 

  29. S. Chehab, Y. Merroun, T. Ghailane, R. Ghailane, S. Boukhris, M. Akhazzane, A. Kerbal, A. Souizi, Russ. J. Org. Chem. 55, 1380 (2019)

    Article  CAS  Google Scholar 

  30. S. Chehab, Y. Merroun, T. Ghailane, N. Habbadi, S. Boukhris, A. Hassikou, R. Ghailane, M. Akhazzane, A. Kerbal, A. Daich, A. Souizi, Med. J. Chem. 7, 56 (2018)

    Google Scholar 

  31. Y. Merroun, S. Chehab, T. Ghailane, M. Akhazzane, A. Souizi, R. Ghailane, React. Kinet. Mech. Catal. 126, 249 (2019)

    Article  CAS  Google Scholar 

  32. A. El Hallaoui, S. Chehab, B. Malek, O. Zimou, T. Ghailane, S. Boukhris, A. Souizi, R. Ghailane, ChemistrySelect 4, 3062 (2019)

    Article  CAS  Google Scholar 

  33. A. El Hallaoui, S. Chehab, T. Ghailane, B. Malek, O. Zimou, S. Boukhriss, A. Souizi, R. Ghailane, Polycycl. Aromat. Compd. 40, 1 (2020)

  34. Office chérifien des phosphates” to be found under https://www.ocpgroup.ma/fr/nos-produits/les-engrais, 2020

  35. M. Matteini, S. Rescic, F. Fratini, G. Botticelli, Int. J. Archit. Heritage. 5, 717 (2011)

    Article  Google Scholar 

  36. S. Balalaie, S. Nikoo, S. Haddadi, Synth. Commun. 38, 2521 (2008)

    Article  CAS  Google Scholar 

  37. P. Salehi, M. Dabiri, A.R. Khosropour, P. Roozbehniya, J Iran Chem Soc. 3, 98 (2006)

    Article  CAS  Google Scholar 

  38. M.G. Dekamin, M. Eslami, A. Maleki, Tetrahedron 69, 1074 (2013)

    Article  CAS  Google Scholar 

  39. N. Hazeri, M.T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashahi, Chin. J. Catal. 35, 391 (2014)

    Article  CAS  Google Scholar 

  40. D. Rajguru, B.S. Keshwal, S. Jain, Chin. Chem. Lett. 24, 1033 (2013)

    Article  CAS  Google Scholar 

  41. R. Mozafari, F. Heidarizadeh, Polyhedron 162, 263 (2019)

    Article  CAS  Google Scholar 

  42. H.F. Niya, N. Hazeri, M.R. Kahkhaie, M.T. Maghsoodlou, Res. Chem. Intermed. 46, 1685 (2020)

    Article  CAS  Google Scholar 

  43. U.V. Mane, M.S. Chavan, B.R. Choudhari, D.V. Mane, J Pharm Chem Biol Sci. 6, 311 (2019)

    Google Scholar 

  44. M. Hajjami, F. Gholamian, R.H.E. Hudson, A.M. Sanati, Catal. Lett. 149, 228 (2019)

    Article  CAS  Google Scholar 

  45. S.S. Pourpanah, S.M. Habibi-Khorassani, M. Shahraki, Chin. J. Catal. 36, 757 (2015)

    Article  CAS  Google Scholar 

  46. A.A. Mohammadi, M.R. Asghariganjeh, A. Hadadzahmatkesh, Arab. J. Chem. 10, S2213 (2017)

    Article  CAS  Google Scholar 

  47. D. Azarifar, Y. Abbasi, Synth. Commun. 46, 745 (2016)

    Article  CAS  Google Scholar 

  48. S.M. Khatat, B. Sadeghi, M. Ghasemi, Inorg Nano-Met Chem. 49, 56 (2019)

    Article  CAS  Google Scholar 

  49. X. Fan, D. Feng, Y. Qu, X. Zhang, J. Wang, P.M. Loiseau, G. Andrei, R. Snoeck, E.D. Clercq, Bioorg. Med. Chem. Lett. 20, 809 (2010)

    Article  CAS  PubMed  Google Scholar 

  50. G. Brahmachari, B. Banerjee, A.C.S. Sustain, Chem. Eng. 2, 411 (2014)

    CAS  Google Scholar 

  51. N. G. Khaligh, T. Mihankhah, M. R. Johan, Org. Prep. Proced. Int. 1945 (2020)

Download references

Author information

Authors and Affiliations

  1. Faculty of Science, Laboratory of Organic, Organometallic and Theoretical Chemistry, University Ibn Tofail, Po Box 133, 14000, Kenitra, Morocco

    Soukaina Chehab, Youssef Merroun, Tourya Ghailane, Rachida Ghailane, Said Boukhris & Abdelaziz Souizi

  2. Faculty of Science, Laboratory of Agricultural Resources, Polymer and Process Engineering, University Ibn Tofail, Po Box 133, 14000, Kenitra, Morocco

    Brahim Lakhrissi

Authors
  1. Soukaina Chehab
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Youssef Merroun
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tourya Ghailane
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Rachida Ghailane
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Said Boukhris
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Brahim Lakhrissi
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Abdelaziz Souizi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Abdelaziz Souizi.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chehab, S., Merroun, Y., Ghailane, T. et al. A facile and efficient synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[4,3-b]pyrans derivatives using phosphate fertilizers MAP, DAP, and TSP as heterogeneous catalysts. J IRAN CHEM SOC 18, 2665–2678 (2021). https://doi.org/10.1007/s13738-021-02223-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-021-02223-x

Keywords

Search

Navigation