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

Autor: Kurt Polborn, Andrey Gavryushin, Grigoriy Ya. Remennikov
Rok vydání: 2015
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 53:537-544
ISSN: 0022-152X
DOI: 10.1002/jhet.2326
Popis: 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.
Databáze: OpenAIRE