期刊
MOLBANK
卷 2023, 期 1, 页码 -出版社
MDPI
DOI: 10.3390/M1603
关键词
voriconazole; late-stage functionalization; hydroxymethylation; photoredox reaction; oxidation; NMR spectroscopy
A new VN derivative, VN-CHO, was synthesized through photoredox-catalyzed hydroxymethylation reaction followed by oxidation. The introduction of a formyl group in VN structure offers a promising site for further functionalization.
Voriconazole (VN) is an antifungal drug indicated for the treatment of several fungal infections. Due to its side effects, some works involving late-stage functionalization of VN have been reported in the literature. Here, we disclose a new VN derivative, the 6-[(2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde (VN-CHO). This compound results from the photoredox-catalyzed hydroxymethylation of VN, affording a hydroxymethylated derivative (VN-CH2OH), followed by oxidation of the former CH2OH group. VN-CHO was obtained in good yield (70% yield) and its structure was unveiled by 1D (H-1 and C-13) and 2D (HSQC and HMBC) NMR techniques. The introduction of a formyl group in VN structure creates a very promising site for further functionalization in a molecule which originally does not have many active sites.
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