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

…, M Jonusis, V Jakubkiene

Index: Cikotiene, Inga; Jonusis, Mantas; Jakubkiene, Virginija Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 1819 - 1825

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Citation Number: 4

Abstract

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 H 2 SO 4 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 ...