Beilstein J. Org. Chem.2020,16, 2739–2748, doi:10.3762/bjoc.16.224
formation of a new derivative of caffeine.
Keywords: adenine; caffeine; cyclic dimer of hexafluorothioacetone; hexafluoroisopropylgroup; purine; 2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithietane; theophylline; Introduction
Despite significant progress in the last 20–30 years, the selective introduction of
fluorine and polyfluoroalkyl substituents into organic molecules remains a challenging problem in the synthesis of fluorinated biologically active compounds, especially larger moieties, such as C2F5, CF(CF3)2, and CH(CF3)2. With respect to the hexafluoroisopropylgroup, the methods are limited to a
for the introduction of a hexafluoroisopropylgroup based on the reaction of tetrakis(trifluoromethyl)-1,3-dithietane (1) with the corresponding azoles [17]. Since this methodology is simple and works for a wide variety of imidazoles, including benzimidazole, we decided to explore the applicability of
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Graphical Abstract
Scheme 1:
Reaction of purine (2) with tetrakis(trifluoromethyl)-1,3-dithietane (1).