Issue 4, 2021
From the journal:

Organic Chemistry Frontiers

Ring expansion and ring opening of 3-halooxindoles with N-alkoxycarbonyl-O-tosylhydroxylamines for divergent access to 4-aminoquinolin-2-ones and N-Cbz-N’-arylureas†

Wei-Cheng Yuan, ORCID logo *a   Jian Zuo,b   Shu-Pei Yuan,b   Jian-Qiang Zhao, ORCID logo *a   Zhen-Hua Wang ORCID logo a  and  Yong You ORCID logo a  

* Corresponding authors

a Institute for Advanced Study, Chengdu University, Chengdu 610106, China
E-mail: yuanwc@cioc.ac.cn, zhaojianqiang@cdu.edu.cn

b National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, China

Abstract

A divergent method for ring expansion and ring opening of 3-halooxindoles has been developed. Under mild base-mediated conditions, 3-halooxindoles generate indolones in situ, which then react smoothly with N-alkoxycarbonyl-O-tosylhydroxylamines to give 4-aminoquinolin-2-ones and N-Cbz-N′-arylureas in good to excellent yields via ring expansion and opening pathways, respectively. This protocol is characterized by easy availability of substrates, user-friendly reaction conditions, broad functional group tolerance, and a simple operation procedure.

Graphical abstract: Ring expansion and ring opening of 3-halooxindoles with N-alkoxycarbonyl-O-tosylhydroxylamines for divergent access to 4-aminoquinolin-2-ones and N-Cbz-N’-arylureas

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Article information

DOI
https://doi.org/10.1039/D0QO01335H
Article type
Research Article
Submitted
28 Oct 2020
Accepted
22 Dec 2020
First published
23 Dec 2020

Org. Chem. Front., 2021,8, 784-791

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Ring expansion and ring opening of 3-halooxindoles with N-alkoxycarbonyl-O-tosylhydroxylamines for divergent access to 4-aminoquinolin-2-ones and N-Cbz-N’-arylureas

W. Yuan, J. Zuo, S. Yuan, J. Zhao, Z. Wang and Y. You, Org. Chem. Front., 2021, 8, 784 DOI: 10.1039/D0QO01335H

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