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Study of chemical behaviors of 4-hydroxycumarin in alkali media: dicumarols or dihydro-4H-furo[3,2-c]chromenes?

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Abstract

A novel method for one-pot reaction of 4-hydroxycoumarin with various aldehydes and trimethylamine (Et3N) leads to dicumarols and quaternary dicumarol-triethylammonium salts in the presence of cyanogen bromide (BrCN). The same reactions were proceeded in the presence of sodium ethoxide (EtONa) that leads to dicumarols in good to excellent yields at room temperature. Exceptionally, 4-hydroxybenzaldehyde in the reaction with 4-hydroxycoumarin and BrCN in the presence of EtONa led to selective and efficacious formation of dihydro-4H-furo [3,2-c] chromene derivative, under the same condition. All structures elucidation was characterized by 1H, 13C NMR, FT-IR spectroscopy. Furocumarin derivative was also specified by X-ray crystallography technique.

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References

  1. A. Kale, C. Bingi, S. Sripada, C.G. Kumar, K. Atmakur, Bioorg. Med. Chem. Lett. 26, 4899 (2016)

    Article  CAS  Google Scholar 

  2. M. Mercep, M. Mesic, B. Hrvacic, I.J. Elenkov, I. Malnar, Furochromene derivative with anti-inflammatory activity, WO2005/095411A1, 2005.

  3. M. Trkovnik, M. Cacic, J. Rizvani, Coumarin derivative as anti-viral agent, pharmaceutical composition thereof, its preparation and use, WO 2016156888 A1, 2016.

  4. A.G. Al-Sehemi, S.R. El-Gogary, Chin. J. Chem. 30, 316 (2012)

    Article  CAS  Google Scholar 

  5. C. Zdero, F. Bohlmann, R.M. King, H. Robinson, Phytochem. 25, 509 (1986)

    Article  CAS  Google Scholar 

  6. M. Miski, J. Jakupovic, Phytochem. 29, 1995 (1990)

    Article  CAS  Google Scholar 

  7. A. Rustalyan, L. Nazarians, F. Bohlmann, Phytochem. 19, 1254 (1980)

    Article  Google Scholar 

  8. G. Hoffmann, R.K. Johnson, J. Nat. Prod. 56, 1500 (1993)

    Article  Google Scholar 

  9. M. Yılmaz, M. Yakut, A.T. Pekel, Synth. Commun. 38, 914 (2008)

    Article  Google Scholar 

  10. G. Feuer, in Progress in Medicinal Chemistry. ed. by G.P. Ellis, G.B. West (North Holland Publishing Co., North New York, 1974)

    Google Scholar 

  11. A.A. Deana, J. Med. Chem. 26, 580 (1983)

    Article  CAS  Google Scholar 

  12. H. Abbasi-Dehnavi, M. Ghashang, Heterocycl. Commun. 24, 19 (2018)

    Article  CAS  Google Scholar 

  13. M.M. Abdou, R.A. El-Saeed, S. Bondock, Arabian J. Chem. 12, 974 (2019)

    Article  CAS  Google Scholar 

  14. L. Jurd, J. Corse, A.D. King, H. Bayne, K. Mihara, Phytochem. 10, 2971 (1971)

    Article  CAS  Google Scholar 

  15. K.P. Link, J. Biol. Chem. 138, 21 (1941)

    Article  Google Scholar 

  16. N. Hamdi, M.C. Puerta, P. Valerga, Eur. J. Med. Chem. 43, 2541 (2008)

    Article  CAS  Google Scholar 

  17. S.M. Saidana, A. Romdhane, M.D. Remadi, H.J. Khiareddine, D. Touboul, H.B. Jannet, M.A. Hamza, Med. Chem. Res. 24, 3247 (2015)

    Article  Google Scholar 

  18. T. Ojala, S. Remes, P. Haansuu, H. Vuorela, R. Hiltunen, K. Haahtela, P. Vuorela, J. Ethnopharmacol. 73, 299 (2000)

    Article  CAS  Google Scholar 

  19. P. Laurin, M. Klich, C. Dupis-Hamelin, P. Mauvais, P. Lassaigne, A. Bonnefoy, B. Musicki, Bioorg. Med. Chem. Lett. 9, 2079 (1999)

    Article  CAS  Google Scholar 

  20. F.G. Medina, J.G. Marrero, M. Macías-Alonso, M.C. González, I. Córdova-Guerrero, A.G.T. García, S. Osegueda-Robles, Nat. Prod. Rep. 32, 1472 (2015)

    Article  CAS  Google Scholar 

  21. I. Kostava, I. Manolov, I. Nicolova, S. Konstantonov, M. Karaivanova, Eur. J. Med. Chem. 36, 339 (2001)

    Article  Google Scholar 

  22. H. Madari, D. Panda, L. Wilson, R. Jacobs, Cancer. Res. 63, 1214 (2003)

    CAS  PubMed  Google Scholar 

  23. P.B. Pansuriya, M.N. Patel, Appl. Organomet. Chem. 21, 719 (2007)

    Article  CAS  Google Scholar 

  24. K.P. Boroujeni, P. Ghasemi, Catal. Commun. 37, 50 (2013)

    Article  Google Scholar 

  25. N. Hassanloie, N. Noroozi Pesyan, G. Sheykhaghaei, Appl. Organomet. Chem. 34, e5242 (2020)

    Article  CAS  Google Scholar 

  26. N. Noroozi Pesyan, A. Gharib, M. Behroozi, A. Shokr, Arabian J. Chem. 10, S1558 (2017)

    Article  CAS  Google Scholar 

  27. N. Noroozi Pesyan, S. Bibak, M. Aalinejad, J. Iran, J. Chem. Soc. 17, 411 (2020)

    CAS  Google Scholar 

  28. M. Aalinejad, N. Noroozi Pesyan, J. Chin. Chem. Soc. 66, 1523 (2019)

    Article  CAS  Google Scholar 

  29. P.B.W. McCallum, M.R. Grimmett, A.G. Blackman, R.T. Weavers, Aust. J. Chem. 52, 159 (1999)

    Article  CAS  Google Scholar 

  30. A.D. Gupta, S. Samanta, R. Mondal, A.K. Mallik, Bull. Korean Chem. Soc. 33, 321 (2012)

    Article  Google Scholar 

  31. W.W. Hartman, E.E. Dreger, Org. Synth. Coll. 2, 150 (1943)

    Google Scholar 

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Correspondence to Nader Noroozi Pesyan.

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Imani, M., Noroozi Pesyan, N., Aalinejad, M. et al. Study of chemical behaviors of 4-hydroxycumarin in alkali media: dicumarols or dihydro-4H-furo[3,2-c]chromenes?. J IRAN CHEM SOC 19, 3397–3405 (2022). https://doi.org/10.1007/s13738-022-02533-8

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