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Novel three-component heterocyclization involving gem-bromofluorocyclopropanes, nitrosylating or nitrating agent and organic nitrile yielding previously unknown 4-fluoropyrimidine 1-oxides was found. A series of 4-fluoropyrimidine 1-oxides was obtained via this reaction and studied under various reduction conditions. Preparative method for the synthesis of 4-fluoropyrimidines 4 from corresponding N-oxides under the treatment of PCl3 was elaborated. 4-Fluorotetrahydroquinazoline N-oxide and tetrahydroquinazoline were studied as model compounds in reactions with various O-, N-, P-nucleophiles and demonstrated high reactivity in aromatic nucleophilic substitution.