Tetrahedron Letters

Mechanistic aspect of ring transformations in the reaction of 5-nitro-4-pyrimidinone with acetophenone derivatives and cycloalkanones depending on the electron …

N Nishiwaki, R Sugimoto, K Saigo, K Kobiro

Index: Nishiwaki, Nagatoshi; Sugimoto, Ryuichi; Saigo, Kazuhiko; Kobiro, Kazuya Tetrahedron Letters, 2013 , vol. 54, # 8 p. 956 - 959

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Citation Number: 3

Abstract

3-Methyl-5-nitro-4-pyrimidinone undergoes two kinds of nucleophilic type ring transformations upon treatment with cycloalkanones in the presence of ammonium acetate, which affords 4, 5-disubstituted pyrimidines and 5, 6-disubstituted 3-nitro-2-pyridones. In order to improve the synthetic utility of this reaction, it is necessary to control the regioselectivity of these ring transformations. In the present work, we performed DFT ...