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Remennikov, Grigoriy Ya; Gavryushin, Andrey; Polborn, Kurt (2016): An Unexpected Pyrimidine Ring Transformations in the Reaction of 4-aryl-5-nitro-6-bromomethylpyrimidin-2(1H)-ones with Anilines. In: Journal of Heterocyclic Chemistry, Vol. 53, No. 2: pp. 537-544
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Abstract

The reaction of 4-aryl-6-bromomethyl-5-nitro-3,4-dihydropyrimidin-2(1H)-ones, containing three possible combinations of substituted and unsubstituted nitrogen atoms with anilines depending on the conditions leads to the products of ring contraction of the pyrimidinone ring into an imidazolone, as well as to the formation of 7-aryl-6,7-dihydroisoxazolo[4,3-d]pyrimidin-5(4H)-one derivatives, and in some cases to the 5-aminopyrimidinones. The mechanisms of these unusual ring transformations are discussed.