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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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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cited_by cdi_FETCH-LOGICAL-c2323-438ff2adfccd755d8faa9a958b591056812623c05b8e2479bf2c428f64016b383
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container_end_page 4126
container_issue 23
container_start_page 4121
container_title Advanced synthesis & catalysis
container_volume 365
creator Ren, Jun‐Jie
Zhou, Jia‐Xin
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description 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.
doi_str_mv 10.1002/adsc.202300773
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source Wiley-Blackwell Read & Publish Collection
subjects Acylation
Cascade reaction
Catalyst- and additive-free
Chemical synthesis
Column chromatography
Double N-acylation
Fused pyrimidinediones
Solvent extraction
Wolff rearrangement
title Cascade Wolff Rearrangement and Double N‐Acylation: A Cyclization of α‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones
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