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2020 , Vol. 40 >Issue 7: 2045 - 2050

DOI: https://doi.org/10.6023/cjoc202001025

研究论文

2,3-二氯-5,6-二氰对苯醌(DDQ)介导的由吲哚啉-2-羧酸合成N-烷基吲哚及1,4-双((1H-吲哚-1-基)甲基)苯的简易方法

  • 朱润宇 ,
  • 翟民 ,
  • 刘霜 ,
  • 刘星彤 ,
  • 王振 ,
  • 居瑞军 ,
  • 虞心红
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  • a 华东理工大学药学院 制药工程与过程化学教育部工程研究中心 上海市 新药设计重点实验室 生物反应器工程国家重点实验室 上海 200237;
    b 临沂大学药学院 山东临沂 276000;
    c 北京石油化工学院 化学工程学院 北京 102617

收稿日期: 2020-01-17

  修回日期: 2020-03-21

  网络出版日期: 2020-04-23

基金资助

国家自然科学基金（Nos.21476078，81703453）和上海市科学技术委员会（No.12431900902）资助项目.

收起

One-Pot Synthesis of N-Alkyl Indole from Indoline-2-carboxylic Acids and Alkyl Halides by 2,3-Dicyano-5,6-dichlorobenzoquinone (DDQ) Mediated Oxidative Decaboylative Aromatization

  • Zhu Runyu ,
  • Zhai Min ,
  • Liu Shuang ,
  • Liu Xingtong ,
  • Wang Zhen ,
  • Ju Ruijun ,
  • Yu Xinhong
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  • a Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, State Key Laboratory of Bioengineering Reactors, School of Pharmacy, East China University of Science & Technology, Shanghai 200237;
    b School of Pharmacy, Linyi University, Linyi, Shandong 276000;
    c College of Chemical Engineering, Beijing Institute of Petrochemical Technology, Beijing 102617

Received date: 2020-01-17

  Revised date: 2020-03-21

  Online published: 2020-04-23

Supported by

Project supported by the National Science Foundation of China (NSFC) (Nos. 21476078, 81703453) and the Science and Technology Commission of Shanghai Municipality (No. 12431900902).

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摘要

报道了通过2，3-二氯-5，6-二氰对苯醌（DDQ）介导的N-烷基二氢吲哚-2-羧酸的分子内氧化脱羧芳构化合成N-烷基吲哚.由于该方法的良好兼容性，继而开发了温和且无金属的从烷基卤化物和二氢吲哚羧酸一锅法合成N-烷基吲哚的方法.还报道了该方法在一锅法三组分合成1，4-双（（1H-吲哚-1-基）甲基）苯中的成功应用.

关键词： 芳构化; 2,3-二氯-5,6-二氰对苯醌(DDQ); 脱羧; N-烷基吲哚; 氧化

本文引用格式

朱润宇 , 翟民 , 刘霜 , 刘星彤 , 王振 , 居瑞军 , 虞心红 . 2,3-二氯-5,6-二氰对苯醌(DDQ)介导的由吲哚啉-2-羧酸合成N-烷基吲哚及1,4-双((1H-吲哚-1-基)甲基)苯的简易方法[J]. 有机化学, 2020 , 40(7) : 2045 -2050 . DOI: 10.6023/cjoc202001025

Abstract

Synthesis of N-alkyl indoles via 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) mediated intramolecular oxidative decarboxylative aromatization of N-alkylindoline-2-carboxylic acids is reported. The good compatibility of this process leads to the development of a mild and metal-free one-pot synthesis of N-alkyl indoles from alkyl halides and indoline carboxylic acid. The one-pot three-component synthesis of 1,4-bis((1H-indol-1-yl)methyl)benzene is also disclosed in satisfied yields.

Key words： aromatization; 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ); decarboxylation; N-alkyl indoles; oxidation

参考文献

[1] Selected reviews on the synthesis of indoles:(a) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
(b) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
(c) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
(d) Lounasmaa, M.; Tolvanen, A. Nat. Prod. Rep. 2000, 17, 175.
[2] (a) Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S. J. Med. Chem. 1988, 31, 2235.
(b) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G. Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939.
[3] (a) Sundberg, R. J. The Chemistry of Indoles, Academic Press, New York, 1970.
(b) Sundberg, R. J. Indoles, Academic Press, London, UK, 1966.
(c) Sexton, J. E. Indoles, Wiley, New York, 1983.
[4] (a) Barbero, N.; San Martin, R.; Domínguez, E. Tetrahedron Lett. 2009, 50, 2129.
(b) Knaack, M.; Emig, P.; Bats, J. W. Eur. J. Org. Chem. 2001, 3843.
[5] (a) Willis, M. C.; Brace, G. N.; Findla. T. J. K.; Holmes, I. P. Adv. Synth. Catal. 2006, 348, 851.
(b) Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem. 2005, 117, 407.
[6] Barluenga, J.; Jiménez-Aquino, A.; Aznar. F.; Valdés, C. J. Am. Chem. Soc. 2009, 131, 4031.
[7] Barluenga, J.; Jiménez-Aquino, A. Angew. Chem., Int. Ed. 2007, 46, 1529.
[8] Bähn, S.; Imm, S.; Mevius, K..; Neubert, L.; Tillack, A.; Williams, J. M. J.; Beller, M. Chem.-Eur. J. 2010, 16, 3590.
[9] For reviews on the Shvo catalyst, see:(a) Samec, J. S. M. Backvall, J. E. e-EROS Encycl. Reagents Org. Synth. 2009, 7, 5557.
(b) Comas-Vives, A.; Ujaque, G.; Lledos, A. J. Mol. Struct.: THEOCHEM 2009, 903, 123.
(c) Karvembu, R.; Prabhakaran, R.; Natarajan, K. Coord. Chem. Rev. 2005, 249, 911.
(d) Prabhakaran, R. Synlett 2004, 2048.
[10] (a) Mays, M. J.; Morris, M. J.; Raithby, P. R.; Shvo, Y.; Czarkie, D. Organometallics 1989, 8, 1162.
(b) Shvo, Y.; Czarkie, D. J. Am. Chem. Soc. 1986, 108, 7400.
(c) Shvo, Y.; Thomasand, D. W.; Laine, R. M. J. Chem. Soc., Chem. Commun. 1980, 249, 753.
[11] Hara, T.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2003, 44, 6207.
[12] Mao, H.; Wang, S.; Yu, P.; Lv, H.; Xu, R. S.; Pan, Y. J. J. Org. Chem. 2011, 76, 1167.
[13] Reddy, K. H. V.; Satish, G.; Ramesh, K.; Karnakar, K.; Nageswar, Y. V. D. Tetrahedron Lett. 2012, 53, 3061.
[14] Wang, J.; Shen, Q.; Zhang, J.; Song, G. Tetrahedron Lett. 2015, 56, 2913.
[15] (a) Tang, M.; Tong, L. F.; Ju, L.; Zhai, W. W.; Hu, Y.; Yu, X. H. Org. Lett. 2015, 17, 5180.
(b) Zou, Z. Q.; Deng, Z. J.; Yu, X. H.; Zhang, M. M.; Zhao, S. H.; Luo, T.; Yin, X.; Xu, H.; Wang, W. Sci. China, Chem. 2012, 55, 43.
[16] For the pioneering work about CuBr-mediated intramolecular oxidative decarboxylation of α-tertiary amino acids, see:Bi, H. P.; Zhao, L.; Liang, Y. M.; Li. C. J. Angew. Chem., Int. Ed. 2009, 48, 792.
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