Chinese Journal of Organic Chemistry >
Alkylation of Indole and Benzofuran with Acetals
Received date: 2014-06-23
Revised date: 2014-08-10
Online 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
Liu Ningning , Yang Ling , Yang Bei , Wang Jinbang , Chen Xue , Wu Qinpei . Alkylation of Indole and Benzofuran with Acetals[J]. Chinese Journal of Organic Chemistry, 2014 , 34(12) : 2523 -2528 . DOI: 10.6023/cjoc201401038
[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.
/
| 〈 |
|
〉 |
