Copper/Nafion-Catalyzed Hydroarylation Process Involving Ketenimine Intermediates: A Novel and Synthetic Approach to 4-Sulfonamidoquinoline-2-ones and Derivatives Thereof

A copper(II)/NafionNR50‐catalyzed cascade is demonstrated, wherein in situ keteneimine formation and hydroarylation processes are involved. Various substituted 4‐sulfonamidoquinolin‐2‐ones and various derivatives thereof were obtained. The robust toluenesulfonamide protecting group can be removed on...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2016-01, Vol.358 (1), p.50-55
Main Authors: Reichart, Benedikt, Guedes de la Cruz, Gema, Zangger, Klaus, Kappe, C. Oliver, Glasnov, Toma
Format: Article
Language:English
Subjects:
Cascades
Catalysis
Copper
cyclization
Demand
Derivatives
Formations
heterocycles
microwave and continuous flow chemistry
Synthesis
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Summary:A copper(II)/NafionNR50‐catalyzed cascade is demonstrated, wherein in situ keteneimine formation and hydroarylation processes are involved. Various substituted 4‐sulfonamidoquinolin‐2‐ones and various derivatives thereof were obtained. The robust toluenesulfonamide protecting group can be removed on demand in a mild light‐promoted process to provide access to otherwise difficult to obtain 4‐aminoquinolin‐2‐ones.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201500942