Nitronium salts as novel reagents for the heterocyclization of gem-bromofluorocyclopropanes into pyrimidine derivatives. Issue 34 (19th August 2015)

• Record Type: Journal Article
• Authors: 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.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 34(2015)
• Page Start: 4927
• Page End: 4930
• Publication Date: 2015-08-19
• Subjects: Cyclopropanes -- Heterocyclization -- Nitronium triflate -- Pyrimidines; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.06.089
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 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 + )(CF3 SO3 − ).