Autoxidation/Aldol Tandem Reaction of 2-Oxindoles with Ketones: A Green Approach for the Synthesis of 3-Hydroxy-2-Oxindoles

In the presence of tetrabutylammonium fluoride and molecular sieves (MS) 4 Å in DMF, an efficient autoxidation reaction of 2‐oxindoles with ketones under air at room temperature has been developed. This approach may provide a green, practical, and metal‐free protocol for a wide range of biologically...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-02, Vol.22 (8), p.2595-2598
Main Authors: Zhang, Qing-Bao, Jia, Wen-Liang, Ban, Yong-Liang, Zheng, Yong, Liu, Qiang, Wu, Li-Zhu
Format: Article
Language:English
Subjects:
Air temperature
Aldehydes
Autoxidation
Cascade chemical reactions
Catalysis
Chemical synthesis
Chemistry
C−H activation
Fluorides
Indoles - chemistry
Ketones
Ketones - chemistry
Molecular chains
Molecular sieves
Oxidation-Reduction
oxindoles
oxygen
Quaternary Ammonium Compounds - chemistry
Stereoisomerism
Synthesis (chemistry)
tetrabutylammonium fluoride
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Summary:In the presence of tetrabutylammonium fluoride and molecular sieves (MS) 4 Å in DMF, an efficient autoxidation reaction of 2‐oxindoles with ketones under air at room temperature has been developed. This approach may provide a green, practical, and metal‐free protocol for a wide range of biologically important 3‐hydroxy‐3‐(2‐oxo‐alkyl)‐2‐oxindoles. A metal‐free autoxidation reaction of 2‐oxindoles with ketones under air at room temperature has been developed (see scheme; TBAF=tetrabutylammonium fluoride). This approach provides a green and practical way to access a wide range of biologically important 3‐hydroxy‐3‐(2‐oxo‐alkyl)‐2‐oxindoles.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201504282