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

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...

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Bibliographic Details
Published inBeilstein journal of organic chemistry Vol. 9; no. 1; pp. 1819 - 1825
Main Authors Cikotiene, Inga, Jonusis, Mantas, Jakubkiene, Virginija
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 06.09.2013
Subjects
5-nitrosopyrimidines
Chemistry
Fischer–Hepp rearrangement
Full Research Paper
nitrosation
nucleophilic substitution
pyrimidinediamines
Fischer–Hepp rearrangement
nitrosation
5-nitrosopyrimidines
pyrimidinediamines
nucleophilic substitution
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Summary: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.
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ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.9.212