Alkylation of Indole and Benzofuran with Acetals

doi:10.6023/cjoc201401038

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2523-2528.DOI: 10.6023/cjoc201401038 Previous Articles Next Articles

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缩醛与吲哚或苯并呋喃的烷基化反应

刘宁宁, 杨玲, 杨蓓, 王金棒, 陈雪, 武钦佩

北京理工大学化工与环境学院北京 100081

收稿日期:2014-06-23 修回日期:2014-08-10 发布日期:2014-08-26
通讯作者: 武钦佩 E-mail:qpwu@bit.edu.cn
基金资助:
国家自然科学基金(No.21172019)资助项目.

Alkylation of Indole and Benzofuran with Acetals

Liu Ningning, Yang Ling, Yang Bei, Wang Jinbang, Chen Xue, Wu Qinpei

School of Chemical Engineering and Environments, Beijing Institute of Technology, Beijing 100081

Received:2014-06-23 Revised:2014-08-10 Published:2014-08-26
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172019).

Benzofuran derivatives and bisindolylmethane derivatives are widely present in natural products, and have significant biological activity. Acetals were demonstrated to be efficient alkylating agents in the presence of TMSOTf and 2,4,6-collidine. Bisbenzofuranmethane and bisindolylmethane derivatives were easily obtained via direct alkylation of benzofurnan or indole with a series of acetals including amino, cyclic, acetone, aryl and alkyl acetals. The reaction mechanism was proposed.

Key words: benzofuran, indole, acetal, alkylation

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Liu Ningning, Yang Ling, Yang Bei, Wang Jinbang, Chen Xue, Wu Qinpei. Alkylation of Indole and Benzofuran with Acetals[J]. Chin. J. Org. Chem., 2014, 34(12): 2523-2528.

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[1] (a) Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Chem. Rev. 2010, 110, 2250. (b) Abe, T.; Nakamura, S.; Yanada, R.; Choshi, T.; Hibino, S.; Ishikura, M. Org. Lett. 2013, 15, 3622. (c) Pang, Y. Y.; Xu, Z. L. Chin. J. Org. Chem. 2005, 25, 25 (in Chinese). (庞翼燕, 许遵乐, 有机化学, 2005, 25, 25.) (d) Pathak, T. P.; Osiak, J. G.; Vaden, R. M.; Welm, B. E.; Sigman, M. S. Tetrahedron 2012, 68, 5203. (e) Gao, X.; Gong, H. J.; Men, P.; Zhou, L.; Ye, D. Y. Chin. J. Chem. 2013, 31, 1164. (f) Zhang, J.; Da, Sh. J.; Feng, X. L.; Chen, X. Y. Chin. J. Chem. 2013, 31, 123. (g) Fang, H. B.; Jin, L.; Huang, N. Y.; Wang, J. Zh.; Zou, K.; Luo, Z. G. Chin. J. Chem. 2013, 31, 831.
[2] Safe, S.; Papineni, S.; Chintharlapalli, S. Cancer Lett. 2008, 269, 326.
[3] (a) Wang, J. R.; Tsai, C. H.; Kulp, S. K.; Chen, C. S. Cancer Lett. 2008, 262, 153. (b) Hall, J. M.; Barhoover, M. A.; Kazmin, D.; McDonnell, D. P.; Greenlee, W. F.; Thomas, R. S. Mol. Endocrinol. 2010, 24, 359. (c) Garikapaty, V. P. S.; Ashok, B. T.; Tadi, K.; Mittelman, A.; Tiwari, R. K. Biochem. Biophys. Res. Commun. 2006, 340, 718.
[4] Bell, R.; Carmeli, S.; Sar, N. J. Nat. Prod. 1994, 57, 1587.
[5] Peng, Y. Y.; Zhang, Q. L.; Yuan, J. J.; Cheng, J. P. Chin. J. Chem. 2008, 26, 2228.
[6] An, L. T.; Ding, F. Q.; Zou, J. P.; Lu, X. H.; Zhang, L. L. Chin. J. Chem. 2007, 25, 822.
[7] He, F.; Li, P.; Gu, Y.; Li, G. Green Chem. 2009, 11, 1767.
[8] Mendes, S. R.; Thurow, S.; Fortes, M. P.; Penteado, F.; Lenardão, E. J.; Alves, D.; Perin, G.; Jacob, R. G. Tetrahedron Lett. 2012, 53, 5402.
[9] Khaksar, S.; Talesh, S. M. J. Fluorine Chem. 2012, 135, 87.
[10] Azizi, N.; Torkian, L.; Saidi, M. R. J. Mol. Catal. A: Chem. 2007, 275, 109.
[11] Zhang, Z.-H.; Yin, L.; Wang, Y.-M. Synthesis 2005, 1949.
[12] Mulla, S. A. R.; Sudalai, A.; Pathan, M. Y.; Siddique, S. A.; Inamdar, S. M.; Chavan, S. S.; Reddy, R. S. RSC Adv. 2012, 2, 3525.
[13] Mo, L. P.; Ma, Z. C.; Zhang, Z. H. Synth. Commun. 2005, 35, 1997.
[14] (a) Ji, S. J.; Zhou, M. F.; Gu, D. G.; Wang, S. Y.; Loh, T. P. Synlett 2003, 2077. (b) Armstrong, E. L.; Grover, H. K.; Kerr, M. A. J. Org. Chem. 2013, 78, 10534.
[15] Lin, H.; Zang, Y.; Sun, X.; Lin, G. Chin. J. Chem. 2012, 30, 2309.
[16] Chen, R. E.; Wang, Y. L.; Chen, Z. W.; Su, W. K. Can. J. Chem. 2008, 86, 875.
[17] (a) Fujioka, H.; Minamitsuji, Y.; Moriya, T.; Okamoto, K.; Kubo, O.; Matsushita, T.; Murai, K. Chem. Asian J. 2012, 7, 1925. (b) Du, T. J.; Wu, Q. P.; Liu, H. X.; Chen, X.; Shu, Y. N.; Xi, X. D.; Zhang, Q. S.; Li, Y. Z. Tetrahedron 2011, 67, 1096. (c) Huang, L.; Yang, H. B.; Zhang, D. H.; Zhang, Z.; Tang, X. Y.; Xu, Q.; Shi, M. Angew. Chem., Int. Ed. 2013, 52, 6767. (d) Wu, Q.; Xi, X.; Chen, X.; Li, H.; Zhang, Q.; Li, Y. Chin. J. Chem. 2009, 27, 1962.
[18] (a) Fujioka, H.; Okitsu, T.; Ohnaka, T.; Li, R.; Kubo, O.; Okamoto, K.; Sawama, Y.; Kita, Y. J. Org. Chem. 2007, 72, 7898. (b) Fujioka, H.; Okitsu, T.; Sawama, Y.; Murata, N.; Li, R.; Kita, Y. J. Am. Chem. Soc. 2006, 128, 5930. (c) Maegawa, T.; Fujioka, H. J. Synth. Org. Chem. Jpn. 2013, 71, 694.
[19] Chen, R. E.; Wang, Y. L.; Chen, Z. W.; Su, W. K. Can. J. Chem. 2008, 86, 875.
[20] Ganguly, N. C.; Mondal, P.; Barik, S. K. Green Chem. Lett. Rev. 2011, 5, 73.
[21] Yang, Y. L.; Xie, Z. F.; Wang, J. D. Chin. J. Chem. 2011, 29, 2091.
[22] Nadkarni, S. V.; Nagarkar, J. M. Green Chem. Lett. Rev. 2011, 4, 121.

缩醛与吲哚或苯并呋喃的烷基化反应

Alkylation of Indole and Benzofuran with Acetals

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