One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides

Junwei Wang; Xiang Pan; Quanjin Rong; Lei Zhao; Lin Zhao; Weichen Dai; Kun Zhao; Lihong Hu

doi:10.1039/D0RA05497F

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One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides†

Junwei Wang,

‡*^a Xiang Pan,‡^a Quanjin Rong,^a Lei Zhao,^a Lin Zhao,^a Weichen Dai,^a Kun Zhao

*^a and Lihong Hu*^a

Author affiliations

* Corresponding authors

^a Jiangsu Key Laboratory for Functional Substances of Chinese Medicine, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, P. R. China
E-mail: jwwang@njucm.edu.cn, kunzhao13@gmail.com, lhhu@njucm.edu.cn

Abstract

A facile one-pot synthesis has been developed through alkylation/acylation of ortho-tosylaminophenyl-substituted para-quinone methides followed by an intramolecular 1,6-conjugate addition and oxidation sequence. This cascade reaction occurs readily in good yield (up to 95%), providing a divergent synthetic approach to structurally diverse 2,3-disubstituted indoles and 3,4-diaryl-substituted quinolinones.

This article is part of the themed collection: 2020 RSC Advances HOT Article Collection

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DOI: https://doi.org/10.1039/D0RA05497F
Article type: Paper
Submitted: 23 Jun 2020
Accepted: 01 Sep 2020
First published: 10 Sep 2020
This article is Open Access

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RSC Adv., 2020,10, 33455-33460

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One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides

J. Wang, X. Pan, Q. Rong, L. Zhao, L. Zhao, W. Dai, K. Zhao and L. Hu, RSC Adv., 2020, 10, 33455 DOI: 10.1039/D0RA05497F

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One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides†

Abstract

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One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides

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