Aminolysis of Methoxy Groups in Pyrimidine Derivatives. Activation by 5-Nitroso Group

M. Melguizo, A. Marchal, M. Nogueras, A. Sánchez

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    Abstract

    The nucleophilic substitution of 2-methoxy groups in pyrimidine derivatives was strongly activated by introduction of a 5-nitroso group on to the pyrimidine ring. The aminolysis of several 2-methoxy-5-nitrosopyrimidine derivatives was performed at room temperature in hydroxylic as well as in non-hydroxylic media with different primary amines in short time and good yields. The aminolysed substrates include 6-[(per-O-acetyl)glycosyl]aminopyrimidines which afforded the corresponding 2-aminopyrimidines without harming the acetyl protecting groups of the sugar moiety.

    Original languageEnglish
    Pages (from-to)97-103
    Number of pages7
    JournalJournal of Heterocyclic Chemistry
    Volume39
    Issue number39
    Publication statusPublished - 2002

    Keywords

    • ANALOGS

    Cite this

    Melguizo, M., Marchal, A., Nogueras, M., & Sánchez, A. (2002). Aminolysis of Methoxy Groups in Pyrimidine Derivatives. Activation by 5-Nitroso Group. Journal of Heterocyclic Chemistry, 39(39), 97-103.