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Issue 12, 2021, Issue in Progress
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t-BuOK mediated oxidative coupling amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines

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Abstract

The transition-metal free amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines, such as various (hetero)aromatic amine and aliphatic amine via t-BuOK-mediated oxidative coupling at room temperature has been developed. This reaction provides efficient access to the biologically important and synthetically useful 2-amino-1,4-naphthoquinones and 2-amino-3-indolylnaphthoquinones with good yields under mild conditions. The present protocol is simple, practical and shows good functional group tolerance. In addition, the obtained 2-amino-3-indolylnaphthoquinones were further transformed to synthesize polycyclic N-heterocycles.

Graphical abstract: t-BuOK mediated oxidative coupling amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines

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Supplementary files

Article information


Submitted
09 Jan 2021
Accepted
01 Feb 2021
First published
08 Feb 2021

This article is Open Access

RSC Adv., 2021,11, 6776-6780
Article type
Paper

t-BuOK mediated oxidative coupling amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines

Y. Dong, T. Mei, Q. Luo, Q. Feng, B. Chang, F. Yang, H. Zhou, Z. Shi, J. Wang and B. He, RSC Adv., 2021, 11, 6776
DOI: 10.1039/D1RA00193K

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