The first example of the Fischer–Hepp type rearrangement in pyrimidines

• Inga Cikotiene,
• Mantas Jonusis and
• Virginija Jakubkiene

Beilstein J. Org. Chem. 2013, 9, 1819–1825, doi:10.3762/bjoc.9.212

• pyrimidine ring changed the outcome of the reaction. Instead of a denitrosation reaction, selective nitroso group migration to C-5 and the formation of 2,4,6-trisubstituted 5-nitrosopyrimidines took place. It is noteworthy that the resulting 5-nitrosopyrimidines are important intermediates for the

• subsequent migration reaction of the nitroso group in activated 6,-N-disubstituted-N-nitrosopyrimidin-4-amines occurs smoothly and allows for the preparation of chemically interesting 2,4,6-trisubstituted 5-nitrosopyrimidines. Conclusion The first example of an intramolecular nitrosogroup transfer in 6,-N

• trisubstituted 5-nitrosopyrimidines. The detailed investigation of the mechanism of this transformation is in progress and will be published in due course. Experimental IR spectra were run in KBr discs on a Perkin-Elmer FT spectrophotometer Spectrum BX II. 1H and 13C NMR spectra were recorded with a Varian Unity