Potassium tert-Butanolate Promoted Reaction of Benzaldehydes and Indoles: a New Strategy for Synthesis of Bis(indolyl) arylmethanes

doi:10.1007/s40242-017-6382-9

高等学校化学研究 ›› 2017, Vol. 33 ›› Issue (2): 200-205.doi: 10.1007/s40242-017-6382-9

Potassium tert-Butanolate Promoted Reaction of Benzaldehydes and Indoles: a New Strategy for Synthesis of Bis(indolyl) arylmethanes

JIANG Chong¹, LI Jue¹, LÜ Guanghui^1,2, ZHENG Yang¹, YU Xinling¹, LÜ Songyang¹, HAI Li¹, WU Yong¹

1. Key Laboratory of Drug-targeting, Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China;
2. Department of Pharmacy, Taihe Hospital, Hubei University of Medicine, Shiyan 442000, P. R. China

收稿日期:2016-09-14 修回日期:2016-10-08 出版日期:2017-04-01 发布日期:2016-11-28
通讯作者: WU Yong,E-mail:wyong@scu.edu.cn E-mail:wyong@scu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(Nos.81373259, 81573286).

Potassium tert-Butanolate Promoted Reaction of Benzaldehydes and Indoles: a New Strategy for Synthesis of Bis(indolyl) arylmethanes

JIANG Chong¹, LI Jue¹, LÜ Guanghui^1,2, ZHENG Yang¹, YU Xinling¹, LÜ Songyang¹, HAI Li¹, WU Yong¹

1. Key Laboratory of Drug-targeting, Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China;
2. Department of Pharmacy, Taihe Hospital, Hubei University of Medicine, Shiyan 442000, P. R. China

Received:2016-09-14 Revised:2016-10-08 Online:2017-04-01 Published:2016-11-28
Contact: WU Yong,E-mail:wyong@scu.edu.cn E-mail:wyong@scu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.81373259, 81573286).

摘要/Abstract

摘要：

t-BuOK-promoted synthesis of bis(indolyl) arylmethanes from aromatic aldehydes and indoles was achieved. Substrates bearing different functional groups, especially groups which are sensitive to acidic media, are well tolerated under the optimal condition, making this reaction particularly attractive for expanding the scope of the present protocols that provides bis(1H-indol-3-yl) arylmethanes.

关键词: Bis(indolyl) arylmethane, Indole, Base-promoted reaction

Abstract:

Key words: Bis(indolyl) arylmethane, Indole, Base-promoted reaction

JIANG Chong, LI Jue, LÜ Guanghui, ZHENG Yang, YU Xinling, LÜ Songyang, HAI Li, WU Yong. Potassium tert-Butanolate Promoted Reaction of Benzaldehydes and Indoles: a New Strategy for Synthesis of Bis(indolyl) arylmethanes[J]. 高等学校化学研究, 2017, 33(2): 200-205.

参考文献

[1] Kimura T., Kanagaki S., Matsui Y., Imoto M., Watanabe T., Shibasaki M., Org. Lett., 2012, 14(17), 4418
[2] Amir M., Javed S. A., Kumar H., Med. Chem. Res., 2010, 19(3), 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(4), 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(3), 177
[7] Selala M. I., Laekeman G. M., Loenders B., Musuku A., Herman A. G., Schepens P., J. Nat. Prod., 1991, 54(1), 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(18), 4376
[9] De Miranda B. R., Miller J. A., Hansen R. J., Lunghofer P. J., Safe S., Gustafson D. L., Colagiovanni D., Tjalkens R. B., J. Pharmacol. Exp. Ther., 2013, 345(1), 125
[10] Andey T., Patel A., Jackson T., Safe S., Singh M., Eur. J. Pharm. Sci., 2013, 50(2), 227
[11] Lee S. O., Andey T., Jin U. H., Kim K., Singh M., Safe S., Oncogene, 2012, 31(27), 3265
[12] Lee S. O., Abdelrahim M., Yoon K., Chintharlapalli S., Papineni S., Kim K., Wang H., Safe S., Cancer Res., 2010, 70(17), 6824
[13] Chintharlapalli S., Burghardt R., Papineni S., Ramaiah S., Yoon K., Safe S., J. Biol. Chem., 2005, 280(26), 24903
[14] Qin C., Morrow D., Stewart J., Spencer K., Porter W., Smith R., Phillips T., Abdelrahim M., Samudio I., Safe S., Mol. Cancer Ther., 2004, 3(3), 247
[15] Sashidhara K.V., Kumar M., Sonkar R., Singh B. S., Khanna A. K., Bhatia G., J. Med. Chem., 2012, 55(6), 2769
[16] Praveen C., Dheenkumar P., Muralidharan D., Perumal P. T., Bioorg. Med. Chem. Lett., 2010, 20(24), 7292
[17] Tjalkens R. B., Liu X., Mohl B., Wright T., Moreno J. A., Carbone D. L., Safe S., J. Neurosci. Res., 2008, 85(3), 618
[18] Chintharlapalli S., Papineni S., Safe S., Mol. Pharmacol., 2007, 71(3), 558
[19] Kassouf W., Chintharlapalli S., Abdelrahim M., Nelkin G., Safe S., Kamat A. M., Cancer Res., 2006, 66(1), 412
[20] Chintharlapalli S., Smith R. III., Samudio I., Zhang W., Safe S., Cancer Res., 2004, 64(17), 5994
[21] Hong H., Samudio I., Liu S., Abdelrahim M., Safe S., Endocrinology, 2004, 145(12), 5774
[22] Chhattise Prakash K., Arbuj Sudhir S., Mohite Kakasaheb C., Bhavsar Sanjay V., Horne Amit S., Handore Kalpana N., Chabukswar Vasant V., RSC Adv., 2014, 4(54), 28623
[23] Porter J. K., Bacon C. W., Robbins J. D., Himmelsbach D. S., Higman H. C., J. Agric. Food Chem., 1977, 25(1), 88
[24] Deb M. L. Bhuyan P. J., Tetrahedron Lett., 2006, 47(9), 1441
[25] Wang Y. M., Wen Z., Chen X. M., Du D. M., Matsuura T., Meng J. B., J. Heterocycl. Chem., 1998, 35(2), 313
[26] Kokare N. D., Sangshetti J. N., Shinde D. B., Chin. Chem. Lett., 2008, 19(10), 1186
[27] Singh P., Singh D., Samant S., Synth. Commun., 2005, 35(16), 2133
[28] Young P. C., Hadfield M. S., Arrowsmith L., MacLeod K. M., Mudd R. J., Jordan-Hore J. A., Lee A. L., Org. Lett., 2012, 14(3), 898
[29] Yang J., Wang Z., Pan F., Li Y., Bao W., Org. Biomol. Chem., 2010, 8(13), 2975
[30] Xia D., Wang Y., Du Z., Zheng Q. Y., Wang C., Org. Lett., 2012, 14(2), 588
[31] Guo X., Pan S., Liu J., Li Z., J. Org. Chem., 2009, 74(22), 8848
[32] Chen D., Yu L., Wang P. G., Tetrahedron Lett., 1996, 37(26), 4467
[33] Sun W. Y., Sun Y., Tang Y. C., Hu J. Q., Synlett., 1993, 1993(5), 337
[34] Wang L., Han J., Tian H., Sheng J., Fan Z., Tang X., Synlett., 2005,2005(2), 337
[35] Mi X., Luo S., He J., Cheng J. P., Tetrahedron Lett., 2004, 45(23), 4567
[36] Karthik M., Magesh C. J., Perumal P. T., Palanichamy M., Arabindoo B., Murugesan V., Appl. Catal., A, 2005, 286(1), 137
[37] Badigenchala S., Ganapathy D., Das A., Singh R., Sekar G., Synthesis, 2014, 46(1), 101
[38] Hui Y., Chen Y., Gong H., Xie Z., Chin. Chem. Lett., 2014, 25(1), 163
[39] Armstrong E. L.; Grover, H. K.; Kerr, M. A. J. Org. Chem., 2013, 78(20), 10534
[40] Osawa T., Namiki M., Tetrahedron Lett., 1983, 24(43), 4719
[41] Yamamoto Y., Kawanishi E., Koga Y., Sakamaki S., Sakamoto T., Ueta K., Matsushita Y., Kuriyama C.; Tsuda-Tsukimoto M., Nomura S., Bioorg. Med. Chem. Lett., 2013, 23(20), 5641
[42] Zhan Z., Li R. J., Zheng Y., Zhou Y., Hai L., Wu Y., Synlett., 2015, 2015(26), 2261
[43] Zheng Y., Li R. J., Zhan Z., Zhou Y., Hai L., Wu Y., Tetrahedron Lett., 2016, 57(1), 41
[44] Li R. J., Zhou Y., Zheng Y., Hai L., Wu Y., Tetrahedron Lett., 2016, 57(26), 2829
[45] Feng X., Zhang Y., Lin Z., Zhao C., Heterocycl. Commun., 2005, 11(5), 427
[46] Kubczyk T. M., Williams S. M., Kean J. R., Davies T. E., Taylor S. H., Graham A. E., Green Chem., 2011, 13(9), 2320
[47] An L., Ding F., Zou J., Lu X., Zhang L., Chinese J. Chem., 2007, 25(6), 822
[48] Ponnaboina T., Soo K. S., J. Org. Chem., 2010, 75(15), 5240
[49] Zhang Z., Yin L., Wang Y., Synthesis, 2005, 2005(12), 1949
[50] Kamble V. T., Bandgar B. P., Bavikar S. N., Chinese J. Chem., 2007, 25(1), 13
[51] Hasaninejad A., Zare A., Sharghi H., Shekouhy M., Khalifeh R., Beni A. S., Zare A. R. M., Can. J. Chem., 2007, 85(6), 416
[52] Shen Z., Ji S., Wang S., Zeng X., Tetrahedron, 2005, 61(44), 10552
[53] Nobuta T., Fujiya A., Tada N., Miura T., Itoh A., Synlett., 2012, 23(20), 2975
[54] Uddin M. I., Buck J. R., Schulte M. L., Tang D., Saleh S. A., Cheung Y. Y., Harp J., Manning H. C., Tetrahedron Lett., 2014, 55(1), 169

Potassium tert-Butanolate Promoted Reaction of Benzaldehydes and Indoles: a New Strategy for Synthesis of Bis(indolyl) arylmethanes

Potassium tert-Butanolate Promoted Reaction of Benzaldehydes and Indoles: a New Strategy for Synthesis of Bis(indolyl) arylmethanes

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