1360179-76-5Relevant academic research and scientific papers
The first example of the Fischer-Hepp type rearrangement in pyrimidines
Cikotiene, Inga,Jonusis, Mantas,Jakubkiene, Virginija
, p. 1819 - 1825 (2013/10/22)
A N-nitroso moiety can be used for the activation of chloropyrimidines toward a nucleophilic substitution reaction with amines. The subsequent treatment of the obtained products with aq H2SO4 can lead to either N-denitrosation to obtain 4,6-pyrimidinediamines or to a Fischer-Hepp type rearrangement to obtain 5-nitroso-4,6-pyrimidinediamines. It was found that the outcome of the reaction strongly depends on the structure of the pyrimidines. Activation of the pyrimidine ring by three groups with a positive mesomeric effect is crucial for the intramolecular nitroso group migration.
Effect of substituent structure on pyrimidine electrophilic substitution: A rebuttal
Jakubkiene, Virginija,?ikotiene, Inga
, p. 2294 - 2298 (2012/04/10)
The report about a series of unexpected and obscure effects influencing the electrophilic nitrosation of activated pyrimidines (Tetrahedron 2007, 63, 5394) was shown to be erroneous. Instead of electrophilic substitution at position 5 of the pyrimidine ring, N-nitrosation of the secondary amino group in the 4-position of the pyrimidine ring took place. Moreover it was shown that the synthetic sequence for the preparation of purines is also incorrect.
