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Eco-compatible synthesis of novel 3-hydroxyflavones catalyzed by KF-impregnated mesoporous natural zeolite clinoptilolite

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Chemistry of Heterocyclic Compounds Aims and scope

A series of novel 3-hydroxyflavones were designed and synthesized under efficient and green one-pot three-component aldol condensation/intramolecular cyclization reaction of 1-[6-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-5-yl]ethanone, substituted benzaldehyde, and hydrogen peroxide in the presence of potassium fluoride /clinoptilolite nanocatalyst in water at room temperature.

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References

  1. Harborne, J. B.; Williams, C. A. Phytochemistry 2000, 55, 481.

    Article  CAS  PubMed  Google Scholar 

  2. Chavan, H. V.; Bandgar, B. P.; Adsul, L. K.; Dhakane, V. D.; Bhale, P. S.; Thakare, V. N.; Masand, V. Bioorg. Med. Chem. Lett. 2013, 23, 1315.

    Article  CAS  PubMed  Google Scholar 

  3. Erdman, J. W.; Balentine, D.; Arab, L.; Beecher, G.; Dwyer, J. T.; Folts, J.; Harnly, J.; Hollman, P., Keen, C. L.; Mazza, G.; Messina, M.; Scalbert, A.; Vita, J.; Williamson, G.; Burrowes, J. J. Nutr. 2007, 137, 718S.

    Article  CAS  PubMed  Google Scholar 

  4. Lima, G. P. P.; Vianello, F.; Corrêa, C. R.; Campos, R. A. D. S.; Borguini, M. G. Food Nutr. Sci. 2014, 5, 1065.

    CAS  Google Scholar 

  5. Craig, W. J. Am. J. Clin. Nutr. 1999, 70, 491S.

    Article  CAS  Google Scholar 

  6. Flavonoids, Chemistry, Biochemistry and Applications; Andersen, O. M.; Markham, K. R., Eds.; Taylor & Francis: Boca Raton, 2006.

  7. Kim, H. P.; Mani, I.; Iversen, L.; Ziboh, V. A. Prostaglandins, Leukotrienes Essent. Fatty Acids 1998, 58, 17.

    Article  CAS  Google Scholar 

  8. Di Carlo, G.; Autore, G.; Izzo, A. A.; Maiolino, P.; Mascolo, N.; Viola, P.; Diurno, M. V.; Capasso, F. J. Pharm. Pharmacol. 1993, 45, 1054.

    Article  PubMed  Google Scholar 

  9. Osman, H. E.; Maalej, N.; Shanmuganayagam, D.; Folts, J. D. J. Nutr. 1998, 128, 2307.

    Article  CAS  PubMed  Google Scholar 

  10. Tapas, A. R.; Sakarkar, D. M.; Kakde, R. B. Trop. J. Pharm. Res. 2008, 7, 1089.

    Article  Google Scholar 

  11. Ren, W.; Qiao, Z.; Wang, H.; Zhu, L.; Zhang, L. Med. Res. Rev. 2003, 23, 519.

    Article  CAS  PubMed  Google Scholar 

  12. Bilto, Y. Y.; Suboh, S.; Aburjai, T.; Abdalla, S. Nat. Sci. 2012, 4, 740.

    Google Scholar 

  13. Yao, L. H.; Jiang, Y. M.; Shi, J.; Tomás-Barberán, F. A.; Datta, N.; Singanusong, R.; Chen, S. S. Plant Foods Hum. Nutr. 2004, 59, 113.

    Article  CAS  PubMed  Google Scholar 

  14. Perez-Vizcaino, F.; Duarte, J. Mol. Aspects Med. 2010, 31, 478.

    Article  CAS  PubMed  Google Scholar 

  15. Peterson, J. J.; Dwyer, J. T.; Jacques, P. F.; McCullough, M. L. Nutr. Rev. 2012, 70, 491.

    Article  PubMed  PubMed Central  Google Scholar 

  16. Britton, R. G.; Horner-Glister, E.; Pomenya, O. A.; Smith, E. E.; Denton, R.; Jenkins, P. R.; Steward, W. P.; Brown, K.; Gescher, A.; Sale, S. Eur. J. Med. Chem. 2012, 54, 952.

    Article  CAS  PubMed  Google Scholar 

  17. Lee, H. S.; Park, K.-S.; Lee, C.; Lee, B.; Kim, D.-E; Chong, Y. Bioorg. Med. Chem. Lett. 2010, 20, 5709.

    Article  CAS  PubMed  Google Scholar 

  18. Yap, S.; Woodman, O. L.; Crack, P. J.; Williams, S. J. J. Bioorg. Med. Chem. Lett. 2011, 21, 5102.

    Article  CAS  Google Scholar 

  19. Sousa, J. L. C.; Proença, C.; Freitas, M.; Fernandes, E.; Silva, A. M. S. Eur. J. Med. Chem. 2016, 119, 250.

    Article  CAS  PubMed  Google Scholar 

  20. Hasan, A.; Sadiq, A.; Abbas, A.; Mughal, E.; Khan, K. M.; Ali, M. Nat. Prod. Res. 2010, 24, 995.

    Article  CAS  PubMed  Google Scholar 

  21. de Miguel, Y. R. J. Chem. Soc., Perkin Trans. 1 2000, 24, 4213.

    Article  Google Scholar 

  22. Sajjadi-Ghotbabadi, H.; Javanshir, S.; Rostami-Charati, F. Catal. Lett. 2016, 146, 338.

    Article  CAS  Google Scholar 

  23. Sajjadi-Ghotbabadi, H.; Javanshir, S.; Rostami-Charati, F. J. Heterocycl. Chem. 2017, 54, 979.

    Article  CAS  Google Scholar 

  24. a Salmanpour, S.; Khalilzadeh, M. A.; Hosseini, A. Comb. Chem. High Throughput Screening 2013, 16, 339. b Khalilzadeh, M. A.; Keipour, H.; Hosseini, A.; Zareyee, D. New J. Chem. 2014, 38, 42. c Hallajian, S.; Khalilzadeh, M. A.; Tajbakhsh, M.; Alipour, E.; Safaei, Z. Comb. Chem. High Throughput. Screening 2015, 18, 486. d Khalilzadeh, M. A.; Hosseini, A.; Pilevar, A. Eur. J. Org. Chem. 2011, 8, 1587.

  25. Mansouri, N.; Rikhtegar, N.; Panahi, H. A.; Atabi, F.; Shahraki, B. K. Environ. Prot. Eng. 2013, 39, 139.

    CAS  Google Scholar 

  26. Tanaka, H.; Yamasaki, N.; Muratani, M.; Hino, R. Mater. Res. Bull. 2003, 38, 713.

    Article  CAS  Google Scholar 

  27. Xu, C.; Sun, J.; Zhao, B.; Liu, Q. Appl. Catal. 2010, 99, 111.

    Article  CAS  Google Scholar 

  28. Nezamzadeh-Ejhieh, A.; Kabiri-Samani, M. J. Hazard. Mater. 2013, 260, 339.

    Article  CAS  PubMed  Google Scholar 

  29. Bunaciu, A. A.; Udristioiu, E. G.; Aboul-Enein, H. Y. Crit. Rev. Anal. Chem. 2015, 45, 289.

    Article  CAS  PubMed  Google Scholar 

  30. Havrdova, M.; Polakova, K.; Skopalik, J.; Vujtek, M.; Mokdad, A.; Homolkova, M.; Tucek, J.; Nebesarova, J.; Zboril, R. Micron 2014, 67, 149.

    Article  CAS  PubMed  Google Scholar 

  31. Bowen, P. J. Dispersion Sci. Technol. 2002, 23, 631.

    Article  CAS  Google Scholar 

  32. Honary, S.; Zahir, F. Trop. J. Pharm. Res. 2013, 12, 255.

    Google Scholar 

  33. Clogston, J. D.; Patri, K. A. Characterization of Nanoparticles Intended for Drug Delivery; McNeil, S. E., Ed.; Humana Press, 2011, Vol. 697, p. 63.

  34. Akbari, B.; Pirhadi Tavandashti, M.; Zandrahimi, M. Iran. J. Mater. Sci. Eng. 2011, 8, 48.

    CAS  Google Scholar 

  35. Vernimmen, J.; Meynen, V.; Cool, P. Beilstein J. Nanotechnol. 2011, 2, 785.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(5), 508–513

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Sajjadi-Ghotbabadi, H., Javanshir, S., Rostami-Charati, F. et al. Eco-compatible synthesis of novel 3-hydroxyflavones catalyzed by KF-impregnated mesoporous natural zeolite clinoptilolite. Chem Heterocycl Comp 54, 508–513 (2018). https://doi.org/10.1007/s10593-018-2297-8

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  • DOI: https://doi.org/10.1007/s10593-018-2297-8

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