Preparation of novel acyl pyrazoles and triazoles by means of oxidative functionalization reactions

Novel acyl pyrazoles and acyl triazoles have been prepared by means of the oxidative amidation of aldehydes in the presence of the requisite azole. Yields range from modest to good in both cases, and some limitations of the substrate scope have been discovered. Acyl pyrazoles were prepared by treatm...

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Bibliographic Details
Published in:Heterocyclic Communications 2023-02, Vol.29 (1), p.471-9
Main Authors: Wadey Geoffrey P., Doherty Katrina E., Sandoval Arturo León, Leadbeater Nicholas E.
Format: Article
Language:English
Subjects:
aldehyde
Aldehydes
nitroxide
Oxidizing agents
oxoammonium salt
Pyrazole
Sodium persulfate
Substrates
triazole
Triazoles
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Summary:Novel acyl pyrazoles and acyl triazoles have been prepared by means of the oxidative amidation of aldehydes in the presence of the requisite azole. Yields range from modest to good in both cases, and some limitations of the substrate scope have been discovered. Acyl pyrazoles were prepared by treatment of a mixture of aldehyde and pyrazole with an oxoammonium salt bearing the nitrate anion. In the case of acyl triazoles, the oxidative functionalization was performed using sodium persulfate as a terminal oxidant in the presence of a catalytic quantity of a nitroxide.
ISSN:0793-0283
2191-0197
DOI:10.1515/hc-2022-0158