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Synthesis 2024; 56(23): 3669-3679
DOI: 10.1055/s-0043-1773490
paper

One-Pot Microwave-Assisted Intramolecular Rearrangement of Pyranone Amide to Pyridone Ester

Uttam Kumar Mishra
a   Department of Chemistry, Birla Institute of Technology, Mesra, Ranchi 835215, India
,
Rajan Kumar
a   Department of Chemistry, Birla Institute of Technology, Mesra, Ranchi 835215, India
,
Ashok Kumar Jha
b   Aragen Life Sciences Pvt. Ltd, IDA Mallapur, Hyderabad, India
,
Chandralata Bal
a   Department of Chemistry, Birla Institute of Technology, Mesra, Ranchi 835215, India
,
Ashoke Sharon  ∗
a   Department of Chemistry, Birla Institute of Technology, Mesra, Ranchi 835215, India
› Author AffiliationsThe authors acknowledge Science and Engineering Research Board (SERB) financial support (SPG/2021/004524).
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Abstract

This investigation presents a novel, cost-effective approach for creating a 2-pyridone core substituted with an ester group through intramolecular rearrangement. This one-step transformation involves an amide-mediated intramolecular transformation of a pyranone to pyridone scaffold, followed by alcoholic-mediated ester formation, in 75–85% yield. Deuterated alcohol was used to confirm the esterification under alcoholic conditions. The reaction requires a nucleophile source from the solvent, which was observed by performing the reaction of three derivatives in CD3OD to obtain the desired carboxylate compounds, replacing -OR with -OCD3. All synthesized compounds were characterized by spectroscopic analysis, and six selected compounds were further confirmed by single-crystal X-ray diffraction studies.

Key words

microwave-assisted method - alcoholic conditions - intramolecular rearrangement - pyranones - pyridones - ORTEP

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1773490.
  • Supporting Information


Publication History

Received: 22 May 2024

Accepted after revision: 06 September 2024

Article published online:
21 October 2024

© 2024. Thieme. All rights reserved

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