76513-88-7Relevant academic research and scientific papers
Synthesis of Trifluoromethylated Purine Ribonucleotides and Their Evaluation as 19F NMR Probes
Baranowski, Marek R.,Chmielinski, Sebastian,Chrominski, Mikolaj,Jemielity, Jacek,Kowalska, Joanna
, p. 3440 - 3453 (2020/03/23)
Protected guanosine and adenosine ribonucleosides and guanine nucleotides are readily functionalized with CF3 substituents within the nucleobase. Protected guanosine is trifluoromethylated at the C8 position under radical-generating conditions in up to 95% yield and guanosine 5′-oligophosphates in up to 35% yield. In the case of adenosine, the selectivity of trifluoromethylation depends heavily on the functional group protection strategy and leads to a set of CF3-modified nucleosides with different substitution patterns (C8, C2, or both) in up to 37% yield. Further transformations based on phosphorimidazolide chemistry afford various CF3-substituted mono- and dinucleoside oligophosphates in good yields. The utility of the trifluoromethylated nucleotides as probes for 19F NMR-based real-time enzymatic reaction monitoring is demonstrated with three different human nucleotide hydrolases (Fhit, DcpS, and cNIIIB). Substrate and product(s) resonances were sufficiently separated to enable effective tracking of each enzymatic activity of interest.
Au@ZnO Core-Shell: Scalable Photocatalytic Trifluoromethylation Using CF3CO2Na as an Inexpensive Reagent under Visible Light Irradiation
Bazyar, Zahra,Hosseini-Sarvari, Mona
supporting information, p. 2345 - 2353 (2019/10/16)
Trifluoromethylation is of significant importance for the synthesis of many small molecules vital for medicinal and agrochemical research. The importance of the CF3 group as well as the related synthetic challenges is so evident that many reagents have been reported for the synthesis of trifluoromethylated compounds, but these typical reagents are expensive and the methods for preparing them are difficult. Here, we report a new scalable and operationally simple trifluoromethylation reaction using sodium trifluoroacetate as a reagent and Au-modified ZnO as a photocatalyst under visible light irradiation. The reaction proceeds via trifluoromethylation of a broad range of aryl halides, arylboronic acids, and arene and heteroarene substrates. Some pharmaceutical and agrochemical compounds have been trifluoromethylated directly to demonstrate the applicability of the method.
Studies on Organic Fluorine Compounds. Part 35. Trifluoromethylation of Pyrimidine- and Purine-nucleosides with Trifluoromethyl-Copper Complex
Kobayashi, Yoshiro,Yamamoto, Kenjiro,Asai, Toyohira,Nakano, Masanori,Kumadaki, Itsumaro
, p. 2755 - 2761 (2007/10/02)
Halogenated nucleoside derivatives were trifluoromethylated using a solution of a trifluoromethyl-copper complex, which was prepared by shaking trifluoromethyl iodide and copper powder in hexamethylphosphoric triamide and filtering off the excess of copper powder.The following trifluoromethylated nucleosides were obtained in moderate to good yields: 5-trifluoromethyl-uridine, -deoxyuridine, -cytidine, -deoxycytidine, and arabinosylcytosine; 8-trifluoromethyl-adenosine, -deoxyadenosine, and -inosine; and 6-trifluoromethylribofuranosylpurine.This procedure offers simple synthesis of many trifluoromethyl compounds.
