Polyfluoroalkylated antipyrines in Pd-catalyzed transformations |
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Authors: | Evgeny V. Shchegolkov Yanina V. Burgart Daria A. Matsneva Sophia S. Borisevich Renata A. Kadyrova Iana R. Orshanskaya Vladimir V. Zarubaev Victor I. Saloutin |
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Affiliation: | Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoi St., 22, Ekaterinburg 620990 Russia.; Ufa Institute of Chemistry, Russian Academy of Sciences, 71 October Ave., Ufa 450054 Russia ; Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira St., Saint-Petersburg 197101 Russia |
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Abstract: | 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 Pd2(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-CF3-antipyrine has a moderate activity against the influenza virus A/Puerto Rico/8/34 (H1N1) and 4-iodo-5-CF3-antipyrine reveals a weak activity against the vaccine virus (strain Copenhagen) and bovine diarrhea virus (strain VC-1).Peculiarities of heterocyclic systems with electron-withdrawing groups (polyfluoroalkyl-containing antipyrines) in Pd-catalyzed C–H arylation and cross-coupling reactions. |
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