Potassium tert-Butanolate promoted reaction of benzaldehydes and indoles: a new strategy for synthesis of bis(indolyl)arylmethanes

Chong Jiang , Jue Li , Guanghui Lü , Yang Zheng , Xinling Yu , Songyang Lü , Li Hai , Yong Wu

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (2) : 200 -205.

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Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (2) : 200 -205. DOI: 10.1007/s40242-017-6382-9
Article

Potassium tert-Butanolate promoted reaction of benzaldehydes and indoles: a new strategy for synthesis of bis(indolyl)arylmethanes

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Abstract

t-BuOK-promoted synthesis of bis(indolyl)arylmethanes from aromatic aldehydes and indoles is achieved. Substrates bearing different functional groups, especially groups which are sensitive to acidic media, are well tole-rated 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.

Keywords

Bis(indolyl)arylmethane / Indole / Base-promoted reaction

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Chong Jiang, Jue Li, Guanghui Lü, Yang Zheng, Xinling Yu, Songyang Lü, Li Hai, Yong Wu. Potassium tert-Butanolate promoted reaction of benzaldehydes and indoles: a new strategy for synthesis of bis(indolyl)arylmethanes. Chemical Research in Chinese Universities, 2017, 33(2): 200-205 DOI:10.1007/s40242-017-6382-9

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References

[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 Ban-chero 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 KV, 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, Bhav-sar Sanjay V, Horne Amit S, Handore Kalpana N, Chabukswar Va-sant V. RSC Adv., 2014, 4(54): 28623.

[23]

Porter J K, Bacon C W, Robbins J D, Himmelsbach D S, Hig-man 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. Synthe-sis, 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.

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