Benzoic acid: an efficient and rapid catalyst for the synthesis of α-hydroxyl(indolyl)ethanones from indoles

Abstract

An efficient method for regioselective Friedel-Crafts alkylations of indole using arylglyoxals in the presence of benzoic acid has been discovered. The reactions proceeded smoothly at room temperature under metalfree conditions and generated the corresponding products in good to excellent yields. This methodology has a broad substrate scope and opens up an interesting and attractive avenue for the synthesis of α-hydroxyl(indolyl)-ethanones.

Keywords

Friedel-Crafts alkylation / Indole / Arylglyoxal / Benzoic acid

References

[1] Kimura T., Kanagaki S., Matsui Y., Imoto M., Watanabe T., Shibasaki M. Org. Lett., 2012, 14: 4418.

[2] Amir M., Javed S. A., Kumar H. Med. Chem. Res., 2010, 19: 299.

[3] Yao C. H., Song J. S., Chen C. T. Eur. J. Med. Chem., 2012, 55: 32.

[4] Kashyap M., Kandekar S., Baviskar A. T. Bioorg. Med. Chem. Lett., 2013, 23: 934.

[5] Sallam A. A., Ayoub N. M., Foudah A. I., Gissendanner C. R., Meyer S. A., El Sayed K. A. Eur. J. Med. Chem., 2013, 70: 594.

[6] Scuteri M. S. d., Miguel M. A., Blanco Viera J., Planes de Banchero E. Mycopathologia, 1992, 120: 177.

[7] Selala M. I., Laekeman G. M., Loenders B., Musuku A., Herman A. G., Schepens P. J. Nat. Prod., 1991, 54: 207.

[8] Mueller R., Mulani I., Basson A. E., Pribut N., Hassam M., Morris L., van Otterlo W. A., Pelly S. C. Bioorg. Med. Chem. Lett., 2014, 24: 4376.

[9] Rudnitskaya A., Huynh K., Toeroek B., Stieglitz K. J. Med. Chem., 2009, 52: 878.

[10] Han X., Ouyang W., Liu B., Wang W., Tien P., Wu S., Zhou H. B. Org. Biomol. Chem., 2013, 11: 8463.

[11] Prathima P. S., Rajesh P., Rao J. V., Kailash U. S., Sridhar B., Rao M. M. Eur. J. Med. Chem., 2014, 84: 155.

[12] Singh P., Mittal A., Bhardwaj A., Kaur S., Kumar S. Bioorg. Med. Chem. Lett., 2008, 18: 85.

[13] Collot V., Schmitt M., Marwah P., Bourguignon J. J., Heterocycles, 1999, 51: 2823.

[14] Mayring L., Severin T. Chem. Ber., 1981, 114: 3863.

[15] Ryang H. S., Sakurai H. J. Chem. Soc. Chem. Commun., 1972, 2: 77.

[16] Hui Y. H., Zhang Q., Jiang J., Lin L. L., Liu X. H., Feng X. M. J. Org. Chem., 2009, 74: 6878.

[17] Dong H. M., Lu H. H., Lu L. Q., Chen C. B., Xiao W. J. Adv. Synth. Catal., 2007, 349: 1597.

[18] Li H. M., Wang Y. Q., Deng L. Org. Lett., 2006, 8: 4063.

[19] Kashikura W., Itoh J. J., Mori K. J., Akiyama T. Chem. Asian J., 2010, 5: 470.

[20] Zhao J. L., Liu L., Zhang H. B., Wu Y. C., Wang D., Chen Y. J. Tetrahedron Lett., 2006, 47: 2511.

[21] Lv J., Zhang L., Zhou Y. M., Nie Z. X., Luo S. Z., Cheng J. P. Angew. Chem. Int. Ed., 2011, 50: 6610.

[22] Toeroek B., Abid M., London G., Esquibel J., Toeroek M., Mhadgut S. C. Angew. Chem. Int. Ed., 2005, 44: 3086.

[23] Moran W. J., MacRory K. L., Rodriguez A. RSC Adv., 2012, 2: 8962.

[24] Olah G. A. Friedel-Crafts Chemistry, 1973, New York: Wiley-Interscience.

[25] Roberts R. M., Khalaf A. A. Friedel-Crafts Alkylation Chemistry, A Century of Discovery, 1984.

[26] Heaney H., Trost B. M., Fleming I. Comprehensive Organic Synthesis, 1991, 2: 733.

[27] Smith M. B. Organic Synthesis, 1994, New York: McGraw-Hill, 1313.

[28] Qin Y. C., Ye J., Jiang B. B., Wang J. D., Yang Y. R. Chem. J. Chinese Universities, 2015, 36(9): 1825.

[29] Lo K. K. W., Tsang K. H. K., Hui W. K., Zhu N. Chem. Commun, 2003, 21: 2704.

[30] Plimmer J. R., Gammon D. W., Ragsdale N. N. Encyclopedia of Agrochemicals, Vol. 3, 2003, New York: John Wiley & Sons.

[31] Ramirez A., Garcia-Rubio S. Curr. Med. Chem., 2003, 10: 1891.

[32] Kang C. M., Zhao X. H., Yu Y. Q., Lü Y. T. Chem. J. Chinese Universities, 2014, 35(3): 550.

[33] Zhang J. J., Lü Y., Jia H. L., Song Y. Y., Sun X. X., Chai D. X., Wang L. Y. Chem. J. Chinese Universities, 2015, 36(10): 1924.

[34] Ivonin S. P., Lapandin A. V., Anishchenko A. A., Shtamburg V. G. Synth. Commun., 2004, 34: 451.

[35] Ivonin S. P., Lapandin A. V., Shtamburg V. G. Chem. Heterocycl. Compd., 2004, 40: 154.

[36] Dong H. M., Lu H. H., Lu L. Q., Chen C. B., Xiao W. J. Adv. Synth. Catal., 2007, 349: 1597.

[37] Chen D., Yu L., Wang P. Tetrahedron Lett., 1996, 37: 4467.

[38] Gothelf A. S., Hansen T., Jørgensen K. A. J. Chem. Soc., Perkin Trans. 1, 2001, 854.

[39] Joule J. A., Mills K., Smith G. F. Heterocyclic Chemistry, 3rd Ed., 1995, London: Chapman & Hall, 312.

[40] Mosslemin M. H., Movahhed A. E. E-J. Chem., 2012, 9: 301.

[41] Batchu H., Batra S. Eur. J. Org. Chem., 2012, 2012: 2935.

[42] Lai P. S., Taylor M. S. Synthesis, 2010, 9: 1449.