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

Abstract

To study the antikinetoplastid structure-activity relationships in 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 pallado-catalyzed Suzuki-Miyaura, Sonogashira and Buchwald-Hartwig cross-coupling reactions which had never been reported at these positions in this series. Thirty-three original compounds were obtained in 4 steps from 2-amino-bromopyridines, allowing a better definition of the antiparasitic pharmacophore.