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2021 , Vol. 41 >Issue 11: 4444 - 4449

DOI: https://doi.org/10.6023/cjoc202107028

研究论文

铁盐催化的高选择性合成2-取代的吡啶并[2,3-b]吲哚衍生物

  • 卢小彪 ,
  • 肖茜 ,
  • 章明 ,
  • 万常峰 ,
  • 侯豪情 ,
  • 万结平
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  • 江西师范大学化学化工学院 南昌 330022

收稿日期: 2021-07-14

  修回日期: 2021-07-28

  网络出版日期: 2021-08-10

基金资助

国家自然科学基金(21402068)

收起

Highly Selective Synthesis of 2-Substituted Pyrido[2,3-b]indole Derivatives Catalyzed by Iron Salts

  • Xiaobiao Lu ,
  • Xi Xiao ,
  • Ming Zhang ,
  • Changfeng Wan ,
  • Haoqing Hou ,
  • Jieping Wan
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  • College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022
* Corresponding author. E-mail:

Received date: 2021-07-14

  Revised date: 2021-07-28

  Online published: 2021-08-10

Supported by

National Natural Science Foundation of China(21402068)

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摘要

多环稠合的芳香含氮杂环化合物是一类非常重要的含氮杂环化合物, 在药物和材料中得到了广泛的应用, 而吡啶并吲哚类化合物是其重要的一类. 目前, 这类化合物的合成方法并不是很多, 基于之前的工作基础, 发展了一个在三氟甲磺酸铁作为催化剂条件下, 利用邻氨基苯乙腈衍生物和3-二甲胺基烯胺酮类化合物作为反应原料, 在温和的反应条件下, 高效地选择性构建2-取代的吡啶并[2,3-b]吲哚结构的方法.

关键词： 吡啶并[2,3-b]吲哚; 铁盐; N; N-二甲基烯胺酮; 高选择性

本文引用格式

卢小彪 , 肖茜 , 章明 , 万常峰 , 侯豪情 , 万结平 . 铁盐催化的高选择性合成2-取代的吡啶并[2,3-b]吲哚衍生物[J]. 有机化学, 2021 , 41(11) : 4444 -4449 . DOI: 10.6023/cjoc202107028

Abstract

Polycyclic aromatic nitrogen-containing heterocyclic compounds are an important class of nitrogen-containing heterocyclic compounds, which have been widely used in drugs and materials, and indole-fused pyridine compounds are one of them. At present, the methods for the synthesis of these compounds were less reported. Based on previous work, a new route to 2-substituted pyrido[2,3-b]indole derivatives was developed, which employed 2-(2-aminophenyl)acetonitrile derivatives and N,N-dimethyl enaminones as the reaction substrates. The reaction provided the desired product with high selectivity and efficiency.

Key words： pyrido[2,3-b]indole; iron salts; N; N-dimethyl enaminones; high selectivity

参考文献

[1]
(a) Raza, H.; King, R. S.; Squires, R. B.; Guengerich, F. P.; Miller, D. W. Drug Metab. Dispos. 1996, 24, 395.
[1]
(b) Jaromin, A.; Kozubek, A.; Suchoszek-Lukaniuk, K.; Malicka- Blaszkiewicz, M.; Peczynska-Czoch, W.; Kaczmarek, L. Drug Delivery 2008, 15, 49.
[2]
(a) Kim, J. S.; Shin-ya, K.; Furihata, K.; Hayakawa, Y.; Seto, H. Tetrahedron Lett. 1997, 38, 3431.
[2]
(b) Shin-ya, K.; Kim, J. S.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Asian Nat. Prod. Res. 2000, 2, 121.
[3]
(a) Takeuchi, T.; Oishi, S.; Watanabe, T.; Ohno, H.; Sawada, J.; Matsuno, K.; Asai, A.; Asada, N.; Kitaura, K.; Fujii, N. J. Med. Chem. 2011, 54, 4839.
[3]
(b) Arzel, E.; Rocca, P.; Grellier, P.; Labaeıd, V.; Frappier, F.; Gueritte, F.; Gaspard, C.; Marsais, F.; Godard, A.; Queguiner, G. J. Med. Chem. 2001, 44, 949.
[4]
(a) Vecchione, M. K.; Sun, A. X.; Seidel, D. Chem. Sci. 2011, 2, 2178.
[4]
(b) Ali, S.; Li, Y. X.; Anwar, S.; Yang, F.; Chen, Z. S.; Liang, Y. M. J. Org. Chem. 2012, 77, 424.
[4]
(c) Gupta, S.; Kumar, B.; Kundu, B. J. Org. Chem. 2011, 76, 10154.
[4]
(d) Liu, J.; Fitzgerald, A. E.; Mani, N. S. J. Org. Chem. 2008, 73, 2951.
[4]
(e) Selvaraj, K.; Swamy, K. C. K. J. Org. Chem. 2018, 83, 15043.
[4]
(f) Wang, P. F.; Chen, C.; Chen, H.; Han, L. S.; Liu, L.; Sun, H. B.; Wen, X. A. Xua, Q. L. Adv. Synth. Catal. 2017, 359, 2339.
[5]
Alcaide, B.; Almendros, P.; Quirs, M. T. Chem.-Eur. J. 2014, 20, 3384.
[6]
Song, Y.; Tang, X. S.; Hou, X. M.; Bai, Y. J. Chin. J. Org. Chem. 2013, 33, 76. (in Chinese)
[6]
(宋阳, 唐雪松, 侯晓萌, 白银娟, 有机化学, 2016, 33, 76.)
[7]
(a) Oliveira, E. O. D.; Brandt, C. A.; Silveira, M. A. B. D. Tetrahedron Lett. 2007, 48, 6393.
[7]
(b) Reddy, G. J.; Latta, D.; Thirupathaiah, C. A. Tetrahedron Lett. 2005, 46, 301.
[7]
(c) Wan, J. P.; Cao, S.; Liu, Y. Y. Org. Lett. 2016, 18, 6034.
[7]
(d) Bernini, R.; Fabrizi, G.; Sferrazza, A.; Cacchi, S. Angew. Chem., Int. Ed. 2009, 48, 8078.
[8]
(a) Gao, Y.; Hu, C. F.; Wen, C. P.; Wan, J. P. ACS Omega 2017, 2, 7784.
[8]
(b) Gao, Y.; Liu, Y. Y.; Wei, L.; Wan, J. P. Res. Chem. Intermed. 2017, 43, 5547.
[8]
(c) Wang, G. D.; Guo, Y. H.; Wan, J. P. Chin. J. Org. Chem. 2020, 40, 645. (in Chinese)
[8]
(王国栋, 郭艳辉, 万结平, 有机化学, 2020, 40, 645.)
[8]
(d) Fu, L. Q.; Cao, X. J.; Wan, J. P.; Liu, Y. Y. Chin. J. Chem. 2020, 38, 254.
[8]
(e) Fu, L. Q.; Wan, J. P. Asian J. Org. Chem. 2019, 8, 767.
[8]
(f) Guo, Y. H.; Xiang, Y. F.; Wei, L.; Wan, J. P. Org. Lett. 2018, 20, 3971.
[9]
(a) Xu, Y. M.; Chen, X. Q.; Wan, C. F.; Liu, J. B.; Wang, Z. Y. J. Org. Chem. 2020, 85, 4354.
[9]
(b) Chen, X. Q.; Li, L.; Wan, C. F.; Liu, J. B. Tetrahedron Lett. 2020, 61, 152334.
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