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

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.

Keywords

Cascade reaction / Phloroglucinol / Trifluoroacetic anhydride(TFAA) / Trifluoroacetic acid(TFA)

References

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

[2] Robak J., Gryglewski R. J. J. Pharmacol., 1996, 48: 555.

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

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

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

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

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

[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.

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

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

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

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

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

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

[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.

[16] Sharghi H., Jokar M. Heterocycles, 2007, 71: 2721.

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

[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.

[19] Li N. G. W.a.n.g.J. X., Liu X. R., Lin C. J., You Q. D., Guo Q. L. Tetrahedron Lett., 2007, 48: 6586.

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

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

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

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

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

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

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

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

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

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

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

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

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

[33] Tedder J. M. Chem. Rev., 1955, 5: 787.

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

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

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

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

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

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

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

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

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

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

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

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

[46] Nithyanandhan J., Jayaraman N. Tetrahedron, 2005, 61: 11184.

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

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

[49] Deme E. J. Org. Chem., 1976, 41: 3769.

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

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

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