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Polyfluoroalkylated antipyrines in Pd-catalyzed transformations

In the direct C–H arylation with arylhalogenides in the presence of Pd(OAc)(2), trifluoromethyl-containing antipyrine reacts very slowly and incompletely owing to the low nucleophilicity of its C4 center. However, it was effective in modifying polyfluoroalkyl-substituted 4-bromo- and 4-iodo antipyri...

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Detalles Bibliográficos
Autores principales: Shchegolkov, Evgeny V., Burgart, Yanina V., Matsneva, Daria A., Borisevich, Sophia S., Kadyrova, Renata A., Orshanskaya, Iana R., Zarubaev, Vladimir V., Saloutin, Victor I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9042801/
https://www.ncbi.nlm.nih.gov/pubmed/35493195
http://dx.doi.org/10.1039/d1ra06967e
Descripción
Sumario:In the direct C–H arylation with arylhalogenides in the presence of Pd(OAc)(2), trifluoromethyl-containing antipyrine reacts very slowly and incompletely owing to the low nucleophilicity of its C4 center. However, it was effective in modifying polyfluoroalkyl-substituted 4-bromo- and 4-iodo antipyrines by the Suzuki and Sonogashira reactions. It was established that using Pd(2)(dba)(3) as catalyst and XPhos as phosphine ligand was the optimal catalytic system for the synthesis of 4-aryl- and 4-phenylethynyl-3-polyfluoroalkyl-antipyrines. Moreover, iodo-derivatives as the initial reagents were found to be more advantageous compared to bromo-containing analogs. It was found that 4-phenylethynyl-5-CF(3)-antipyrine has a moderate activity against the influenza virus A/Puerto Rico/8/34 (H1N1) and 4-iodo-5-CF(3)-antipyrine reveals a weak activity against the vaccine virus (strain Copenhagen) and bovine diarrhea virus (strain VC-1).