Amidate ion‐mediated intramolecular ring transformation of 2‐pyrones to 2‐pyridones

Herein, we report a new and cost‐effective methodology for synthesizing N‐substituted 2‐pyridone‐3‐carboxylic acids (2) from 2‐pyrone‐3‐carboxamides (1) with a good yield at room temperature. The notable feature of this reaction is the promotion of amidate ion formation mediated by NaH to initiate i...

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Veröffentlicht in:Journal of heterocyclic chemistry 2023-09, Vol.60 (9), p.1641-1646
Hauptverfasser: Kumar, Rajan, Kumari, Neha, Kaur, Harpreet, Bal, Chandralata, Sharon, Ashoke
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein, we report a new and cost‐effective methodology for synthesizing N‐substituted 2‐pyridone‐3‐carboxylic acids (2) from 2‐pyrone‐3‐carboxamides (1) with a good yield at room temperature. The notable feature of this reaction is the promotion of amidate ion formation mediated by NaH to initiate intramolecular ring transformation. In addition to ring transformation, simultaneous decarboxylation and substitution under the metal‐free condition in one pot have been achieved to yield N‐substituted 2‐pyridones (3) from 1. A metal and catalyst free one‐pot method to synthesize 2‐pyridone derivatives through intramolecular nucleophilic attack by amidate‐ion on 2‐pyrone‐3‐carboxamides.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4671