SIOC English
有机化学
高级检索

有机化学 >

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

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

研究论文

环状磷酸催化合成二吲哚甲烷衍生物

  • 何林 ,
  • 王湘波 ,
  • 杜广芬 ,
  • 代斌 ,
  • 简腾跃
展开
  • a 石河子大学化学化工学院 新疆兵团化工绿色过程重点实验室-省部共建国家重点实验室培育基地 石河子 832000;
    b 中国科学院化学研究所 北京分子科学国家实验室 中国科学院分子识别与功能重点实验室 100190

收稿日期: 2012-12-06

  修回日期: 2013-01-27

  网络出版日期: 2013-02-05

基金资助

石河子大学团队创新(No. 2011ZRKETD-0403)、中国科学院分子识别与功能重点实验室2009年开放基金(No. 2009LMRF002)资助项目.

收起

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

摘要

在环状磷酸催化下, 通过吲哚和醛酮的亲电取代反应, 室温下合成了一系列二吲哚甲烷衍生物. 考察了催化剂结构、用量和溶剂等因素对反应的影响, 确定了最优反应条件, 提出了可能的反应机理. 该方法具有操作简单、条件温和、催化剂用量少、产率高及环境友好等优点.

关键词： 吲哚; 醛; 酮; 环状磷酸; 二吲哚甲烷

本文引用格式

何林 , 王湘波 , 杜广芬 , 代斌 , 简腾跃 . 环状磷酸催化合成二吲哚甲烷衍生物[J]. 有机化学, 2013 , 33(05) : 988 -994 . DOI: 10.6023/cjoc201212006

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

参考文献

[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
文章导航

/

〈 〉