Nitronium salts as novel reagents for the heterocyclization of gem-bromofluorocyclopropanes into pyrimidine derivatives
2015
Sedenkova, Kseniya N. | Averina, Elena B. | Grishin, Yuri K. | Bacunov, Aleksandr B. | Troyanov, Sergey I. | Morozov, Igor V. | Deeva, Evgeniya B. | Merkulova, Anna V. | Kuznetsova, Tamara S. | Zefirov, Nikolay S.
A number of nitrosonium and nitronium salts were probed as reagents for the heterocyclization of 1-bromo-1-fluorocyclopropanes in the presence of organic nitriles to give pyrimidine N-oxides. Nitronium triflate, either preformed or generated in situ from nitric and triflic acids, was shown to be the most efficient reagent for this reaction, affording a mild and convenient procedure for the synthesis of 4-halogenopyrimidine derivatives. X-ray crystallography was used to confirm the ionic structure of nitronium triflate (NO2⁺)(CF3SO3⁻).
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