3 Some Pyrimidines of Biological and Medicinal Interest—Part III
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Heterocyclization of gem-dichlorocyclopropanes: “Fine tuning” of reactivity towards nitronium triflate
2017, Tetrahedron LettersCitation Excerpt :1,3-Diazaheterocycles, which contain halogens at the o- or p-positions in relation to the nitrogen atoms and, therefore, can be readily modified via SNAr or cross-coupling processes, represent common synthetic intermediates in the construction of heterocyclic compound libraries for bioactivity screening.2 However, approaches to halogenopyrimidines are mostly restricted to halogenation of the pyrimidine ring, while the direct synthesis via heterocyclization is represented by significantly fewer examples3 Previously, we reported the heterocyclization of gem-bromofluorocyclopropanes I to give 4-fluoropyrimidine N-oxides II upon treatment with nitrosating or nitrating reagents in the presence of organic nitriles (Scheme 1), and preparative approaches towards various pyrimidine derivatives based on this reaction.4
General Overview
2014, Best Synthetic Methods: Organophosphorus (V) Chemistry