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Microwave-assisted synthesis of 4-oxo-2-butenoic acids by aldol-condensation of glyoxylic acid

Lookup NU author(s): Melanie Uguen, Professor Mike Waring

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

© The Royal Society of Chemistry 2021.4-Oxobutenoic acids are useful as biologically active species and as versatile intermediates for further derivatisation. Currently, routes to their synthesis can be problematic and lack generality. Reaction conditions for the synthesis of 4-oxo-2-butenoic acid by microwave-assisted aldol-condensation between methyl ketone derivatives and glyoxylic acid have been developed. They provide the desired products in moderate to excellent yields for a wide range of substrates, by applying a simple procedure to accessible starting materials. The investigation revealed different conditions are required depending on the nature of the methylketone substituent, with aryl derivatives proceeding best using tosic acid and aliphatic substrates reacting best with pyrrolidine and acetic acid. This substituent effect is rationalised by frontier orbital calculations. Overall, this work provides methods for synthesis of 4-oxo-butenoic acids across a broad range of substrates.

Publication metadata

Author(s): Uguen M, Gai C, Sprenger LJ, Liu H, Leach AG, Waring MJ

Publication type: Article

Publication status: Published

Journal: RSC Advances

Year: 2021

Volume: 11

Issue: 48

Pages: 30229-30236

Online publication date: 05/10/2021

Acceptance date: 01/09/2021

Date deposited: 01/11/2021

ISSN (electronic): 2046-2069

Publisher: Royal Society of Chemistry

URL: https://doi.org/10.1039/d1ra05539a

DOI: 10.1039/d1ra05539a

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