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Synlett
DOI: 10.1055/a-2770-5473
Letter

A New Route for the Oxidative Cleavage of Substituted Carbonylfurans as an Approach to 4-Oxobutanoic Acids

Authors

  • Ilya Tkachenko 

    1   Organic chemistry, chemical-technological faculty, Samara State Technical University, Samara, Russian Federation (Ringgold ID: RIN65056)

  • Natalia Alexeevna Ivanova 

    2   Organic chemistry, Samara State Technical University, Samara, Russian Federation (Ringgold ID: RIN65056)

  • Kristina Sergeevna Khrapovitskaya 

    2   Organic chemistry, Samara State Technical University, Samara, Russian Federation (Ringgold ID: RIN65056)

  • Olga Lodochnikova 

    3   Laboratory of diffraction research methods, A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan, Russian Federation

  • Yuri Nikolaevich Klimochkin 

    4   Department of Organic Chemistry, Samara State Technical University, Samara, Russian Federation

Funding Information The research was funded by the Russian Science Foundation (project no. 25-73-20144).
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Graphical Abstract

Abstract

A novel approach to 4-oxobutanoic acids via the oxidative cleavage of 5-substituted 2-carbonylfurans is proposed. Optimization studies using various peroxide-based oxidation agents and other reaction conditions were performed. The obtained ketoacids have potential as precursors for synthesizing 4-substituted GABA analogues and racetams. The synthetic potential of γ-ketoacids was demonstrated through a series of transformations involving 4-oxo-4-(adamantan-1-yl)butanoic acid as the model substrate.

Keywords

Furoic acid - Furan - Oxidative cleavage - 4-Oxobutanoic acid - Persulfate

Supplementary Material



Publication History

Received: 15 October 2025

Accepted after revision: 10 December 2025

Accepted Manuscript online:
11 December 2025

Article published online:
07 January 2026

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