SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 05: 988 - 994

DOI: https://doi.org/10.6023/cjoc201212006

Articles

Synthesis of Bis(indolyl)methanes Catalyzed by Cyclic Phosphoric Acid

  • He Lin ,
  • Wang Xiangbo ,
  • Du Guangfen ,
  • Dai Bin ,
  • Jian Tengyue
Expand
  • a Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan and School of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832000;
    b National Laboratory for Molecular Sciences, Chinese Academy of Sciences Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190

Received date: 2012-12-06

  Revised date: 2013-01-27

  Online published: 2013-02-05

Supported by

Project supported by the Team Innovation Project of Shihezi University (No. 2011ZRKETD-0403), the Key Laboratory of Molecular Recognition and Function, Chinese Academy of Sciences (No. 2009LMRF002).

Fold

Abstract

Cyclic phosphoric acid was found to be an efficient Brønsted acid catalyst for the electrophilic substitution reaction of indole with aldehydes or ketones in dichloromethane to afford the corresponding bis(indolyl)methanes in excellent yields at room temperature. The influence of catalyst structure, catalyst loading and reaction media was investigated, the optimal reaction conditions were obtained and a possible mechanism for the reaction was proposed. The simple procedure, mild reaction conditions, low catalyst loading, high yield and environmentally friendly organocatalyst provide a valuable approach for the preparation of bis(indolyl)methanes.

Key words： indole; aldehyde; ketone; cyclic phosphoric acid; bis(indolyl)methanes

Cite this article

He Lin , Wang Xiangbo , Du Guangfen , Dai Bin , Jian Tengyue . Synthesis of Bis(indolyl)methanes Catalyzed by Cyclic Phosphoric Acid[J]. Chinese Journal of Organic Chemistry, 2013 , 33(05) : 988 -994 . DOI: 10.6023/cjoc201212006

References

[1] (a) Porter, J. K.; Bacon, C. W.; Robins, J. D.; Himmel-sbach, D. S.; Higman, H. C. J. Agric. Food Chem. 1977, 25, 88.
(b) Osawa, T.; Namiki, M. Tetrahedron Lett. 1983, 24, 4719.
(c) Fahy, E.; Potts, B. C. M.; Faulkner, D. J.; Smith, K. J. Nat. Prod. 1991, 54, 564.
(d) Bell, R.; Carmell, N.; Sar. S. J. Nat. Prod. 1994, 57, 1587.
(e) Garbe, T. R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M.; Yuka-wa, H. J. Nat. Prod. 2000, 63, 596.
[2] Rahimizadeh, M.; Eshghi, H.; Bakhtiarpoor, Z.; Pordel, M. J. Chem. Res. 2009, 269.
[3] Povszsz, L.; Katakin, G. P.; Foleat, S.; Malkovics, B. Acta Phys. Acad. Sci. Hung. 1996, 29, 299.
[4] Jitendra, R. S.; Kalpesh, D. P.; Radha, V. J. Catal. Commun. 2008, 9, 1071.
[5] Gong, H.-W.; Xie, Z.-F. Chin. J. Org. Chem. 2012, 32, 1195 (in Chinese).
(宫海伟, 解正峰, 有机化学, 2012, 32, 1195.)
[6] Azizian, J.; Teimouri, F.; Mohammadizadeh, M. R. Catal. Commum. 2007, 8, 1117.
[7] Peng, Y. Y.; Zhang, Q. L.; Yuan, J. J.; Cheng, J. P. Chin. J. Chem. 2008, 26, 2228.
[8] Ghorbani-Vaghei, R.; Veisi, H.; Keypour, H. Mol. Diversity 2010, 14, 87.
[9] Yadav, J. S.; Gupta, M. K.; Jain, R.; Yadav, N. N.; Subba Reddy, B. V. Monatsh. Chem. 2010, 14, 1001.
[10] Li, J.-T.; Lin, Z.-P. Chin. J. Org. Chem. 2008, 28, 1238 (in Chinese).
(李记太, 蔺志平, 有机化学, 2008, 28, 1238.)
[11] Pore, D. M.; Desai, U. V.; Thopate, T. S.; Wadgaonkar, P. P. ARKIVOC 2006, (xii), 75.
[12] (a) Ji, S. J.; Wang, S. Y.; Zhang, Y.; Loh, T. P. Tetrahedron 2004, 60, 2051.
(b) Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959.
[13] Yi, W.-G.; Jia, Z.-Y.; Li, N.-B.; Qiu, R.-H.; Chen, J.-Y.; Xu, X.-H. Chin. J. Org. Chem. 2012, 32, 2390 (in Chinese).
(易卫国, 贾振永, 李宁波, 邱仁华, 陈锦杨, 许新华, 有机化学, 2012, 32, 2390.)
[14] Wang, H.-S.; Zhao, L.-F. Chin. J. Org. Chem. 2005, 25, 869 (in Chinese).
(王宏社, 赵立芳, 有机化学, 2005, 25, 869.)
[15] Chen, D.; Yu, L.; Wang, P. G. Tetrahedron Lett. 1996, 37, 4467;
[16] Nagarajan, R.; Perumal, P. T. Tetrahedron. 2002, 58, 1229.
[17] Babu, G.; Sridhar, N.; Perumal, P. T. Synth. Commun. 2000, 30, 1609.
[18] Mo, L. P.; Ma, Z. C.; Zhang, Z. H. Synth. Commun. 2005, 1997.
[19] Qu, H. E.; Xiao, C.; Hu, Q. S.; Wang, N.; Yu, K. H.; Liu, L. X. Molecules 2011, 16, 3855.
[20] Nagawade, R. R.; Shinde, D. B. Acta Chim. Slov. 2006, 53, 210.
[21] Terada, M.; Sorimachi, K.; Uraguchi, D. Synlett 2006, 0133.
[22] He, Q. L.; Sun, F. L.; Zheng, X. J.; You, S. L. Synlett 2009, 1111.
[23] Wang, X. B.; He. L.; Jian, T. Y.; Ye, S. Chin. Chem. Lett. 2012, 23, 13.
[24] Wang, X.-B.; Jian, T.-Y.; Ma, X.-W.; He. L. Chin. J. Org. Chem. 2012, 32, 2181 (in Chinese).
(王湘波, 简腾跃, 马晓伟, 何林, 有机化学, 2012, 32, 2181.)
[25] Li, J. T.; Sun, S. F. Eur.-J. Chem. 2010, 7(3), 922.
[26] Ghorbani-Vaghei, R.; Veisi, H.; Keypour, H.; Dehghani- Firouzabadi, A. A. Mol. Diversity 2010, 14, 87.
[27] Vahdat, S. M.; Khaksar, S.; Baghery, S. Lett. Org. Chem. 2012, 9, 138.
[28] Nagawade, R. R.; Shinde, D. B. Bull. Korean Chem. Soc. 2005, 26, 1962.
[29] Ghorbani-Vaghei, R.; Malaekehpoor, S. M. Org. Prep. Proced. Int. 2010, 42, 175.
[30] Sheng, S. R.; Wang, Q. Y.; Ding, Y.; Liu, X. L.; Cai, M. Z. Catal. Lett. 2009, 128, 418.
[31] Zhang, Y.; Chen, X.; Liang, J.; Shang, Z.-C. Synth. Commun. 2011, 41, 2446.
[32] Rajitha, B.; Reddy, P. N.; Kumar, B. S.; Sreenivasulu, N.; Reddy, Y. R. T. J. Chem. Res. 2005, 4, 222.
Options
Outlines

/

〈 〉