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Temperature-controlled cascade reaction of phloroglucinoltribenzyl ether promoted by trifluoroacetic anhydride and trifluoroacetic acid

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Abstract

We report the first trifluoroacetic anhydride- and trifluoroacetic acid-promoted cascade reaction with phloroglucinoltribenzyl ether and carboxylic acid as starting materials. By simply varying the temperature of systems containing the same starting materials, different products were produced in high yields. A three-step consecutive reaction process was also proposed.

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References

  1. Harborne J. B., Mabry T. J., The Flavonoids, Academic Press, New York, 2000

    Google Scholar 

  2. Robak J., Gryglewski R. J., J. Pharmacol., 1996, 48, 555

    CAS  Google Scholar 

  3. Pietta P. G., J. Nat. Prod., 2000, 63, 1035

    Article  CAS  Google Scholar 

  4. Desouza R. F., Degiovani W. F., Redox. Re., 2004, 9, 97

    Article  CAS  Google Scholar 

  5. Fylaktakidou K. C., Hadjipavlou-Litina D. J., Litinas K. E., Nicolaides D. N., Curr. Pharm. Des., 2004, 10, 3813

    Article  CAS  Google Scholar 

  6. Weber K. C., Honório K. M., Bruni A. T., Dasilva A. B., J. Mol. Model., 2006, 12, 915

    Article  CAS  Google Scholar 

  7. Hadjipavlou-Litina D., Kontogiorgis C., Pontiki E., Dakanali M., Akoumianaki A., Katerinopoulos H. E. J., Enzyme. Inhib. Med. Chem., 2007, 22, 287

    Article  CAS  Google Scholar 

  8. Fink M. P., Macias C. A., Xiao J., Tyurina Y. Y., Delude R. L., Greenberger J. S., Kagan V. E., Wipf P., Crit. Care. Med., 2007, 35, 461

    Article  Google Scholar 

  9. Jeon K. I., Park E., Park H. R., Jeon Y. J., Cha S. H., Lee S. C., J. Med. Food, 2006, 9, 42

    Article  Google Scholar 

  10. Comte G., Daskiewicz J. B., Bayet C., Conseil G., Viornery-Vanier A., Dumontet C., Dipietro A., BarronD., J. Med. Chem., 2001, 44, 763

    Article  CAS  Google Scholar 

  11. Urgaonkar S., La-Pierre H. S., Meir I., Lund H., Ray-Chaudhuri D., Shaw J. T., Org. Lett., 2005, 7, 5609

    Article  CAS  Google Scholar 

  12. Hufford C. D., Lasswell W. L., J. Org. Chem., 1976, 41, 1297

    Article  CAS  Google Scholar 

  13. Lasswell W. L., Hufford C. D., J. Org. Chem., 1977, 42, 1295

    Article  CAS  Google Scholar 

  14. Achenbach H., Höhn M., Waibel R., Nkunya M. H., Jonker S. A., Muhie S., Phytochemistry, 1997, 44, 359

    Article  CAS  Google Scholar 

  15. Roelens F., Heldring N., Dhooge W., Bengtsson M., Comhaire F., Gustafsson J. A., Treuter E., De-Keukeleire D., J. Med. Chem., 2006, 49, 7357

    Article  CAS  Google Scholar 

  16. Sharghi H., Jokar M., Heterocycles, 2007, 71, 2721

    Article  CAS  Google Scholar 

  17. Gerard B., Cencic R., Pelletier J., Porco J. A., Angew. Chem. Int. Ed., 2007, 46, 7831

    Article  CAS  Google Scholar 

  18. Castanheiro R. A., Pinto M. M., Silva A. M., Cravo S. M., Gales L., Damas A. M., Nazareth N., Nascimento M. S., Eaton G., Bioorg. & Med. Chem., 2007, 15, 6080

    Article  CAS  Google Scholar 

  19. Li N. G., WangJ. X., Liu X. R., Lin C. J., You Q. D., Guo Q. L., Tetrahedron Lett., 2007, 48, 6586

    Article  CAS  Google Scholar 

  20. Urgaonkar S., Shaw J. T., J. Org. Chem., 2007, 72, 4582

    Article  CAS  Google Scholar 

  21. Li K., Tunge J. A., J. Comb. Chem., 2008, 10, 170

    Article  CAS  Google Scholar 

  22. Lin S., Lu X., J. Org. Chem., 2007, 72, 9757

    Article  CAS  Google Scholar 

  23. Esquivias J., Arrayas R. G., Carretero J. C., Angew. Chem. Int. Ed., 2006, 45, 629

    Article  CAS  Google Scholar 

  24. Okamoto K. I., Nishibayashi Y., Uemura S., Toshimitsu A., Angew. Chem., Int. Ed., 2005, 44, 3588

    Article  CAS  Google Scholar 

  25. Li H., Homan E. A., Lampkins A. J., Ghiviriga I., Castellano R. K., Org. Lett., 2005, 7, 443

    Article  CAS  Google Scholar 

  26. Mondal M., Puranik V. G., Argade N. P., J. Org. Chem., 2007, 72, 2068

    Article  CAS  Google Scholar 

  27. Pal. S. I., Bharate S. B., Natural Product Reports, 2006, 23, 558

    Article  Google Scholar 

  28. Friscic T., Drab D. M., Macgillivray L. R., Org. Lett., 2004, 6, 4647

    Article  CAS  Google Scholar 

  29. Qi J., Porco J. A., J. Am. Chem. Soc., 2007, 129, 12682

    Article  CAS  Google Scholar 

  30. Zhang Y. B., Zhang P. Y., Dai G. F., Liu H. M., Syn. Com., 2007, 37, 3319

    Article  CAS  Google Scholar 

  31. Zhou C., Larock R. C., J. Org. Chem., 2006, 71, 3551

    Article  CAS  Google Scholar 

  32. Pineschi M., Bertolini F., Crotti P., Macchia F., Org. Lett., 2006, 8, 2627

    Article  CAS  Google Scholar 

  33. Tedder J. M., Chem. Rev., 1955, 5, 787

    Article  Google Scholar 

  34. Metro T. X., Gomez P. D., Cossy J., J. Org. Chem., 2008, 73, 707

    Article  CAS  Google Scholar 

  35. Ong W. W., Beeler A. B., Kesavan S., Panek J. S., Porco J. A., Angew. Chem. Int. Ed., 2007, 46, 7470

    Article  CAS  Google Scholar 

  36. Chen Y., Porco J. A., Panek J. S., Org. Lett., 2007, 9, 1529

    Article  CAS  Google Scholar 

  37. Lazareva A., Daugulis O., Org. Lett., 2006, 8, 5211

    Article  CAS  Google Scholar 

  38. Firouzabadi H., Iranpoor N., Nowrouzi F., Tetrahedron Lett., 2003, 44, 5343

    Article  CAS  Google Scholar 

  39. Nay B., Arnaudinaud V., Vercauteren J., Eur. J. Org. Chem., 2001, 2379

    Google Scholar 

  40. Arnaudinaud V., Nay B., Nuhrich A., Deffieux G., Merillon J. M., Monti J. P., Vercauteren J., Tetrahedron Lett., 2001, 42, 1279

    Article  CAS  Google Scholar 

  41. Hamura T., Ibusuki Y., Uekusa H., Matsumoto T., Siegel J., Baldridge K., Suzuki K., J. Am. Chem. Soc., 2006, 128, 10032

    Article  CAS  Google Scholar 

  42. Hmed N., Van L., Johan E., Tetrahedron Lett., 2006, 47, 5345

    Article  Google Scholar 

  43. Mallavadhani U. V., Sahoo L., Roy S., Indian J. Chem. Section B, 2004, 2175

    Google Scholar 

  44. Li T. S., Li A. X., J. Chem. Soc., Perkin Tran. 1: Org. Bioorg. Chem., 1998, 1913

    Google Scholar 

  45. Li A. X., Li, T. S., Ding T. H., Chem. Commun., 1997, 1389

    Google Scholar 

  46. Nithyanandhan J., Jayaraman N., Tetrahedron, 2005, 61, 11184

    Article  CAS  Google Scholar 

  47. Kawamoto H., Nakatsubo F., Murakami K., Syn. Commun., 1996, 26, 531

    Article  CAS  Google Scholar 

  48. Schmidt R. R., Effenberger G., Carbohydrate Research, 1987, 171, 59

    Article  CAS  Google Scholar 

  49. Deme E., J. Org. Chem., 1976, 41, 3769

    Article  CAS  Google Scholar 

  50. Li B. N., Wang Y. K., Du D. M., Xu J. X., J. Org. Chem., 2007, 72, 990

    Article  CAS  Google Scholar 

  51. Xu J. X., Wei T. Z., Zhang Q. H., J. Org. Chem., 2003, 68, 10146

    Article  CAS  Google Scholar 

  52. Fletcher S., Gunning P. T., Tetrahedron Lett., 2008, 49, 4817

    Article  CAS  Google Scholar 

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Correspondence to Jianqi Li.

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Supported by the National Natural Science Foundation of China(No.51209024).

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Li, B., Du, L. & Li, J. Temperature-controlled cascade reaction of phloroglucinoltribenzyl ether promoted by trifluoroacetic anhydride and trifluoroacetic acid. Chem. Res. Chin. Univ. 32, 380–384 (2016). https://doi.org/10.1007/s40242-016-5508-9

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  • DOI: https://doi.org/10.1007/s40242-016-5508-9

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