Novel Procedure for Selective C-Nitrosation of Aminopyrimidine Derivatives Under Neutral Conditions

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

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    26 Citations (Scopus)

    Abstract

    A novel simple method, based on treatment with isoamyl nitrite (IAN) in DMSO without any added acid, to produce selective C(5)-nitrosation of aminopyrimidine derivatives is described. It proved to be suitable for a multigram scale and applicable to a larger range of pyrimidine derivatives, including amino-dialkoxypyrimidines, than the procedures previously known. Its scope is analyzed and some example on the usefulness of the newly prepared substances as intermediates in the synthesis of fused heterobicyclic derivatives of potential biological interest is presented.

    Original languageEnglish
    Pages (from-to)255-258
    Number of pages3
    JournalSynlett
    Issue number2
    Publication statusPublished - 2002

    Keywords

    • electrophilic aromatic substitutions
    • heterocycles
    • C-nitrosation
    • nucleoside analogues
    • pyrimidines
    • HUMAN O-6-ALKYLGUANINE-DNA ALKYLTRANSFERASE
    • INHIBITION
    • ANALOGS

    Cite this

    Marchal, A., Melguizo, M., Nogueras, M., & Sánchez, A. (2002). Novel Procedure for Selective C-Nitrosation of Aminopyrimidine Derivatives Under Neutral Conditions. Synlett, (2), 255-258.