Temperature-controlled Cascade Reaction of Phloroglucinoltribenzyl Ether Promoted by Trifluoroacetic Anhydride and Trifluoroacetic Acid

doi:10.1007/s40242-016-5508-9

高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (3): 380-384.doi: 10.1007/s40242-016-5508-9

Temperature-controlled Cascade Reaction of Phloroglucinoltribenzyl Ether Promoted by Trifluoroacetic Anhydride and Trifluoroacetic Acid

LI Bonan¹, DU Lijun², LI Jianqi¹

1. Novel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, Shanghai 201203, P. R. China;
2. School of Life Science, Tsinghua University, Beijing 100084, P. R. China

收稿日期:2015-12-28 修回日期:2016-02-16 出版日期:2016-06-01 发布日期:2016-04-05
通讯作者: LI Jianqi E-mail:lijianqb@126.com
基金资助:
Supported by the National Natural Science Foundation of China(No.51209024).

Temperature-controlled Cascade Reaction of Phloroglucinoltribenzyl Ether Promoted by Trifluoroacetic Anhydride and Trifluoroacetic Acid

LI Bonan¹, DU Lijun², LI Jianqi¹

1. Novel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, Shanghai 201203, P. R. China;
2. School of Life Science, Tsinghua University, Beijing 100084, P. R. China

Received:2015-12-28 Revised:2016-02-16 Online:2016-06-01 Published:2016-04-05
Contact: LI Jianqi E-mail:lijianqb@126.com
Supported by:
Supported by the National Natural Science Foundation of China(No.51209024).

摘要/Abstract

摘要：

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.

关键词: Cascade reaction, Phloroglucinol, Trifluoroacetic anhydride(TFAA), Trifluoroacetic acid(TFA)

Abstract:

Key words: Cascade reaction, Phloroglucinol, Trifluoroacetic anhydride(TFAA), Trifluoroacetic acid(TFA)

LI Bonan, DU Lijun, LI Jianqi. Temperature-controlled Cascade Reaction of Phloroglucinoltribenzyl Ether Promoted by Trifluoroacetic Anhydride and Trifluoroacetic Acid[J]. 高等学校化学研究, 2016, 32(3): 380-384.

参考文献

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

Temperature-controlled Cascade Reaction of Phloroglucinoltribenzyl Ether Promoted by Trifluoroacetic Anhydride and Trifluoroacetic Acid

Temperature-controlled Cascade Reaction of Phloroglucinoltribenzyl Ether Promoted by Trifluoroacetic Anhydride and Trifluoroacetic Acid

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