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

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

    Research output: Contribution to journalArticle

    16 Citations (Scopus)

    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.

    Aminolysis of Methoxy Groups in Pyrimidine Derivatives. Activation by 5-Nitroso Group. / Melguizo, M.; Marchal, A.; Nogueras, M.; Sánchez, A.

    In: Journal of Heterocyclic Chemistry, Vol. 39, No. 39, 2002, p. 97-103.

    Research output: Contribution to journalArticle

    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, vol. 39, no. 39, pp. 97-103.
    Melguizo, M. ; Marchal, A. ; Nogueras, M. ; Sánchez, A. / Aminolysis of Methoxy Groups in Pyrimidine Derivatives. Activation by 5-Nitroso Group. In: Journal of Heterocyclic Chemistry. 2002 ; Vol. 39, No. 39. pp. 97-103.
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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.",
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    AU - Nogueras, M.

    AU - Sánchez, A.

    PY - 2002

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    AB - 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.

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