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Synlett 2019; 30(05): 615-619
DOI: 10.1055/s-0037-1610689
letter
© Georg Thieme Verlag Stuttgart · New York

A One-Pot Approach to 2-(N-Substituted Amino)-1,4-naphthoquinones with Use of Nitro Compounds and 1,4-Naphthoquinones in Water

Xu-Ling Chen
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China   Email: jiyuwang@cioc.ac.cn
b   University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Yu Dong
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China   Email: jiyuwang@cioc.ac.cn
b   University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Shuai He
c   University of the Southwest Minzu, Chengdu 610041, P. R. of China
,
Rui Zhang
c   University of the Southwest Minzu, Chengdu 610041, P. R. of China
,
Hua Zhang
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China   Email: jiyuwang@cioc.ac.cn
b   University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Lei Tang
d   Laboratory of Anaesthesia & Critical Care Medicine, Translational Neuroscience Center, and Department of Anaesthesiology, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China
,
Xiao-Mei Zhang
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China   Email: jiyuwang@cioc.ac.cn
,
Ji-Yu Wang*
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China   Email: jiyuwang@cioc.ac.cn
› Author AffiliationsThis work is supported by CAS ‘Light of West China’ Program.
Further Information

Publication History

Received: 10 December 2018

Accepted after revision: 10 January 2019

Publication Date:
07 February 2019 (online)

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Abstract

A one-pot synthesis of 2-(N-substituted amino)-1,4-naphthoquinones from 1,4-naphthoquinones and nitro compounds in water has been developed. This method features mild reaction conditions and provides aromatic nitro compounds with various functional groups such as halogens, methylthio, ester, amide, even allyl, propargyl, and heterocycles, as well as aliphatic nitro compounds that are well tolerated. This method can be scaled up and we conducted further transformation of the obtained 2-(N-substituted amino)-1,4-naphthoquinones to synthesize carbazolequinone derivatives.

Key words

amines - 1,4-naphthoquinones - nitro compounds - one-pot reactions - reactions in water - carbazolequinones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610689.
  • Supporting Information
 

  • References and Notes

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