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Synthesis and Antiviral Evaluation of 5-(4-Aryl-1,3-butadiyn-1-yl)-uridines and Their Phosphoramidate Pronucleotides.
Molecules
December 2024
Institute of Organic and Analytical Chemistry (ICOA UMR 7311), CNRS, University of Orleans, F-45067 Orléans, France.
The emergence of RNA viruses driven by global population growth and international trade highlights the urgent need for effective antiviral agents that can inhibit viral replication. Nucleoside analogs, which mimic natural nucleotides, have shown promise in targeting RNA-dependent RNA polymerases (RdRps). Starting from protected 5-iodouridine, we report the synthesis of -substituted-(1,3-diyne)-uridines nucleosides and their phosphoramidate prodrugs.
View Article and Find Full Text PDFCopper-Catalyzed Defluorinative [3 + 2] Cyclization of Amidines and Trifluoromethyl Carbenoids for the Synthesis of 5-Fluoroimidazoles.
Org Lett
November 2024
State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi, 830046, Xinjiang, People's Republic of China.
A Cu-catalyzed [3 + 2] cyclization of amidines with trifluoromethyldiazo compounds is described. The reaction affords 5-fluoroimidazoles in good yields by cleaving dual C-F bonds in a CF group. Using 2-aminoazo heterocycles as the substrates, various annelated imidazoles containing a fluorine atom were also constructed by this method without changing the conditions.
View Article and Find Full Text PDFCopper-Catalyzed Trifunctionalization of Heteroaryl-Substituted 1-Hexenes via Remote Heteroaryl Migration.
Chem Asian J
December 2024
Hebei Normal University for Nationalities, Chengde, Hebei Province, China.
A copper-catalyzed trifunctionalization (trifluoromethylation, heteroarylation, and cyanation) of heteroaryl-substituted 1-hexenes via remote heteroaryl migration is reported. A variety of CF and heteroaryl-containing nitriles were readily constructed under mild conditions. The reaction features high chemo- and regioselectivities and represents a convenient method for the synthesis of multifunctionalized molecules in organic synthesis.
View Article and Find Full Text PDFSubstituent-Controlled Copper-Catalyzed Trifluoromethylation of 1,7-Dienes: Synthesis of Mono- and Bis-trifluoromethylated Benzoxepines.
Org Lett
August 2024
Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China.
A copper-catalyzed trifluoromethylation of benzene-linked 1,7-dienes with 1-trifluoromethyl-1,2-benziodoxole via a radical cascade cyclization process for the synthesis of mono- and bis-trifluoromethylated benzoxepines is developed. The selectivity depends on substituents on the double bond of the allyl group in 1,7-dienes. The large-scale operation and late-stage functionalization of bioactive molecules reveal the promising utility of this protocol.
View Article and Find Full Text PDFCopper-catalyzed highly switchable defluoroborylation and hydrodefluorination of 1-(trifluoromethyl)alkynes.
Nat Commun
August 2024
School of Food and Biological Engineering, Hefei University of Technology, Hefei, China.
CF-containing compounds hold significant potential in drug discovery, organic synthesis, and materials science. However, synthesizing various CF-containing building blocks from a single compound remains challenging. Here, we present a Cu-catalyzed, switchable defluoroborylation and hydrodefluorination of trifluoromethylated alkynes, yielding four types of CF-containing compounds.
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