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One-step synthesis of favipiravir from Selectfluor® and 3-hydroxy-2-pyrazinecarboxamide in an ionic liquid. | LitMetric

One-step synthesis of favipiravir from Selectfluor® and 3-hydroxy-2-pyrazinecarboxamide in an ionic liquid.

Org Biomol Chem

Grupo de Química Orgánica Medicinal, Instituto de Química Biológica, Facultad de Ciencias, Universidad de la República, 11400 Montevideo, Uruguay.

Published: May 2023

AI Article Synopsis

  • Favipiravir is a selective antiviral that gained interest as a treatment for COVID-19, but its traditional synthesis involves complicated multi-step processes with low yields.
  • A new, one-step method for making favipiravir has been developed, using direct fluorination with Selectfluor® in a more efficient and eco-friendly way, achieving a higher yield of 50%.
  • This new process takes advantage of an ionic liquid (BF-BMIM) to overcome challenges faced in the standard methods, streamlining production without needing special catalysts or additives.

Article Abstract

Favipiravir is an important selective antiviral that emerged as an alternative against COVID-19 during the pandemic. Its synthesis has gained great interest and the conventional strategies proceed through multiple-step protocols (6-7 reaction steps), which involve, in addition, several drawbacks with global yields, lower than 34%. Herein, a simple, economical, eco-friendly and scalable (1 g) one-step protocol for the synthesis of favipiravir from the direct fluorination of the available 3-hydroxy-2-pyrazinecarboxamide with Selectfluor® is reported. The reaction proceeds easily in BF-BMIM through a simple operational work-up, affording the favipiravir with a yield of 50% without the need of a special catalyst/additive. The key point of the present strategy was the use of the ionic liquid of BF-BMIM, which helps to minimize the several chemical limitations derived from 3-hydroxy-2-pyrazinecarboxamide as a substrate for the direct Selectfluor-mediated fluorination. All these chemical reactivity aspects are also discussed in detail.

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Source
http://dx.doi.org/10.1039/d3ob00380aDOI Listing

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