Three-component heterocyclization of gem-bromofluorocyclopropanes with NOBF4: access to 4-fluoropyrimidine N-oxides.
Novel three-component heterocyclization involving gem-bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the heterocyclization are discussed.
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow 119991, Russia.
Kseniya N
KN
Sedenkova
Elena B
EB
Averina
Yuri K
YK
Grishin
Andrei G
AG
Kutateladze
Victor B
VB
Rybakov
Tamara S
TS
Kuznetsova
Nikolay S
NS
Zefirov
D000475:Alkenes / Q000737:chemistry; D003497:Cyclic N-Oxides; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
D000475:Alkenes; D003497:Cyclic N-Oxides; D003521:Cyclopropanes; D006846:Hydrocarbons, Halogenated; D009570:Nitriles; D012997:Solvents