The first example of the Fischer-Hepp type rearrangement in pyrimidines.

ABSTRACT: 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.

SUBMITTER: Cikotiene I 

PROVIDER: S-EPMC3778328 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature