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Chinese Journal of Organic Chemistry >

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

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

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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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

Cite this article

Zhu Runyu , Zhai Min , Liu Shuang , Liu Xingtong , Wang Zhen , Ju Ruijun , Yu Xinhong . 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[J]. Chinese Journal of Organic Chemistry, 2020 , 40(7) : 2045 -2050 . DOI: 10.6023/cjoc202001025

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