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Synthesis 2024; 56(08): 1297-1308
DOI: 10.1055/a-2232-8113
DOI: 10.1055/a-2232-8113
paper
Synthesis of New 5- or 7-Substituted 3-Nitroimidazo[1,2-a]pyridine Derivatives Using SNAr and Palladium-Catalyzed Reactions To Explore Antiparasitic Structure–Activity Relationships
Authors
This research was funded by Aix-Marseille Université (AMU), the Centre National de la Recherche Scientifique (CNRS), and by Assistance Publique – Hôpitaux de Marseille (AP-HM).
Abstract
To study the antikinetoplastid structure–activity relationships in a 3-nitroimidazo[1,2-a]pyridine series, we explored the substitution of positions 5 and 7 of the scaffold, developing nucleophilic aromatic substitution reactions and palladium-catalyzed Suzuki–Miyaura, Sonogashira, and Buchwald–Hartwig cross-coupling reactions that had never been reported at these positions in this series. In four steps from 2-amino(bromo)pyridines, 33 original compounds were obtained, allowing a better definition of the antiparasitic pharmacophore.
Key words
nitroaromatic compounds - imidazo[1,2-a]pyridines - kinetoplastids - nucleophilic aromatic substitution - palladium-catalyzed cross-coupling reactions - microwave irradiationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2232-8113.
- Supporting Information (PDF)
Publikationsverlauf
Eingereicht: 24. Oktober 2023
Angenommen nach Revision: 19. Dezember 2023
Accepted Manuscript online:
19. Dezember 2023
Artikel online veröffentlicht:
19. Januar 2024
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