Published 2024-12-15
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Organic synthesis of racemic warfarin by addition of an α-β unsaturated

DOI: https://doi.org/10.22490/26194759.9202
Clara S. Varón Universidad Colegio Mayor de Cundinamarca
Cristian C. Ramirez Universidad Colegio Mayor de Cundinamarca
Denise V. Quintero Universidad Colegio Mayor de Cundinamarca

Objective. The goal of this work is to develop a synthetic route for the production of warfarin (RS)-4-hydroxy-3-(1-phenyl-3-oxo-butyl)-coumarin, a chemical compound with both anticoagulant and rodenticidal properties. This is achieved through a Michael addition reaction between 4-hydroxycoumarin and an α,β-unsaturated compound in a basic medium. Methodology. The synthesis of warfarin is carried out by employing a Michael addition reaction between 4-hydroxycoumarin and an α,β-unsaturated compound. The reaction is performed in a basic medium to facilitate the formation of a reactive intermediate. Warfarin, a synthetic derivative of coumarin, is obtained in its racemic form, consisting of the (R) and (S) enantiomers, which differ significantly in their potency, metabolism, and interactions with other substances. Results. The synthesis of warfarin is successfully achieved using the Michael addition method, resulting in a racemic mixture of the (R) and (S) enantiomers. The formation of optical isomers is confirmed through analytical techniques, such as nuclear magnetic resonance (NMR) spectroscopy and chromatography. Additionally, the synthesized warfarin demonstrates anticoagulant properties that are consistent with those reported in the literature. Conclusion. The development of a synthetic route via the Michael addition reaction has proven to be an effective strategy for obtaining warfarin. The racemic mixture produced exhibits the expected anticoagulant and rodenticidal properties. This methodology can be further optimized to enhance enantiomer separation and scalability, holding significant potential for pharmaceutical applications.

keywords: α-β unsaturated, Racemic warfarin., Anticoagulant, Ketone, Aldehyde, Tautomerization
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How to Cite
Varón, C. S., Ramirez, C. C., & Quintero, D. V. (2024). Organic synthesis of racemic warfarin by addition of an α-β unsaturated. Biociencias, 8(1), 99-109. https://doi.org/10.22490/26194759.9202
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