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

doi:10.6023/cjoc202001025

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2045-2050.DOI: 10.6023/cjoc202001025 Previous Articles Next Articles

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^a, 翟民^a, 刘霜^a, 刘星彤^a, 王振^b, 居瑞军^c, 虞心红^a

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 发布日期:2020-04-23
通讯作者: 王振, 居瑞军, 虞心红 E-mail:wangzhen@lyu.edu.cn;juruijun@bipt.edu.cn;xhyu@ecust.edu.cn
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.

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^a, Zhai Min^a, Liu Shuang^a, Liu Xingtong^a, Wang Zhen^b, Ju Ruijun^c, Yu Xinhong^a

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:2020-01-17 Revised:2020-03-21 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.

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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

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

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