An Unexpected Pyrimidine Ring Transformations in the Reaction of 4-aryl-5-nitro-6-bromomethylpyrimidin-2(1H)-ones with Anilines

Remennikov, Grigoriy Ya; Gavryushin, Andrey and 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

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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0022-152X
• Language: English