Benzoic Acid: an Efficient and Rapid Catalyst for the Synthesis of α-Hydroxyl(indolyl)ethanones from Indoles

doi:10.1007/s40242-016-5301-9

高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (2): 212-218.doi: 10.1007/s40242-016-5301-9

Benzoic Acid: an Efficient and Rapid Catalyst for the Synthesis of α-Hydroxyl(indolyl)ethanones from Indoles

LÜ Guanghui, CHENG Xu, ZHENG Yang, LI Weijian, HAI Li, WU Yong

Key Laboratory of Drug-targeting, Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China

收稿日期:2015-07-23 修回日期:2015-10-22 出版日期:2016-04-01 发布日期:2015-12-14
通讯作者: HAI Li, WU Yong E-mail:smile@scu.edu.cn;wyong@scu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.81373259).

Benzoic Acid: an Efficient and Rapid Catalyst for the Synthesis of α-Hydroxyl(indolyl)ethanones from Indoles

LÜ Guanghui, CHENG Xu, ZHENG Yang, LI Weijian, HAI Li, WU Yong

Key Laboratory of Drug-targeting, Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China

Received:2015-07-23 Revised:2015-10-22 Online:2016-04-01 Published:2015-12-14
Contact: HAI Li, WU Yong E-mail:smile@scu.edu.cn;wyong@scu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.81373259).

摘要/Abstract

摘要：

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.

关键词: Friedel-Crafts alkylation, Indole, Arylglyoxal, Benzoic acid

Abstract:

Key words: Friedel-Crafts alkylation, Indole, Arylglyoxal, Benzoic acid

LÜ Guanghui, CHENG Xu, ZHENG Yang, LI Weijian, HAI Li, WU Yong. Benzoic Acid: an Efficient and Rapid Catalyst for the Synthesis of α-Hydroxyl(indolyl)ethanones from Indoles[J]. 高等学校化学研究, 2016, 32(2): 212-218.

参考文献

[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., Sala de 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, Wiley-Interscience, New York, 1973
[25] Roberts R. M., Khalaf A. A., Friedel-Crafts Alkylation Chemistry, A Century of Discovery, Marcel Dekker, New York, 1984
[26] Heaney H.; Eds.:Trost B. M., Fleming I., Comprehensive Organic Synthesis, Pergamon, New York, 1991, 2, 733
[27] Smith M. B., Organic Synthesis, McGraw-Hill, New York, 1994, 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, John Wiley &Sons, New York, 2003
[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., Chapman & Hall, London, 1995, 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

Benzoic Acid: an Efficient and Rapid Catalyst for the Synthesis of α-Hydroxyl(indolyl)ethanones from Indoles

Benzoic Acid: an Efficient and Rapid Catalyst for the Synthesis of α-Hydroxyl(indolyl)ethanones from Indoles

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