Cascade Wolff Rearrangement and Double N‐Acylation: A Cyclization of α‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones

A cascade Wolff rearrangement and double N‐acylation reaction has been developed for the synthesis of fused pyrimidinediones in one‐pot under air. These reactions were performed with α‐diazoketones and 2‐aminopyridines or 3‐aminopyrazoles under catalyst‐ and additive‐free conditions. The protocol av...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-12, Vol.365 (23), p.4121-4126
Main Authors: Ren, Jun‐Jie, Zhou, Jia‐Xin, Song, Yanqin, Zhang, An‐Xin, Zhao, Lu‐Xin, Zhao, Zun‐Yuan, Zhu, Yan‐Ping, Zhu, Wei
Format: Article
Language:English
Subjects:
Acylation
Cascade reaction
Catalyst- and additive-free
Chemical synthesis
Column chromatography
Double N-acylation
Fused pyrimidinediones
Solvent extraction
Wolff rearrangement
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Summary:A cascade Wolff rearrangement and double N‐acylation reaction has been developed for the synthesis of fused pyrimidinediones in one‐pot under air. These reactions were performed with α‐diazoketones and 2‐aminopyridines or 3‐aminopyrazoles under catalyst‐ and additive‐free conditions. The protocol avoided traditional purification procedures, such as organic solvent extraction and column chromatography. The synthesis of biologically active molecules and gram‐scale experiment demonstrated the potential applications of this reaction.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300773