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

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

    Research output: Contribution to journalArticle

    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.

    Novel Procedure for Selective C-Nitrosation of Aminopyrimidine Derivatives Under Neutral Conditions. / Marchal, A.; Melguizo, M.; Nogueras, M.; Sánchez, A.

    In: Synlett, No. 2, 2002, p. 255-258.

    Research output: Contribution to journalArticle

    Marchal, A, Melguizo, M, Nogueras, M & Sánchez, A 2002, 'Novel Procedure for Selective C-Nitrosation of Aminopyrimidine Derivatives Under Neutral Conditions', Synlett, no. 2, pp. 255-258.
    Marchal, A. ; Melguizo, M. ; Nogueras, M. ; Sánchez, A. / Novel Procedure for Selective C-Nitrosation of Aminopyrimidine Derivatives Under Neutral Conditions. In: Synlett. 2002 ; No. 2. pp. 255-258.
    @article{b5645f8d14894a6495465881dddbf14f,
    title = "Novel Procedure for Selective C-Nitrosation of Aminopyrimidine Derivatives Under Neutral Conditions",
    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.",
    keywords = "electrophilic aromatic substitutions, heterocycles, C-nitrosation, nucleoside analogues, pyrimidines, HUMAN O-6-ALKYLGUANINE-DNA ALKYLTRANSFERASE, INHIBITION, ANALOGS",
    author = "A. Marchal and M. Melguizo and M. Nogueras and A. S{\'a}nchez",
    year = "2002",
    language = "English",
    pages = "255--258",
    journal = "Synlett",
    issn = "0936-5214",
    publisher = "Georg Thieme Verlag",
    number = "2",

    }

    TY - JOUR

    T1 - Novel Procedure for Selective C-Nitrosation of Aminopyrimidine Derivatives Under Neutral Conditions

    AU - Marchal, A.

    AU - Melguizo, M.

    AU - Nogueras, M.

    AU - Sánchez, A.

    PY - 2002

    Y1 - 2002

    N2 - 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.

    AB - 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.

    KW - electrophilic aromatic substitutions

    KW - heterocycles

    KW - C-nitrosation

    KW - nucleoside analogues

    KW - pyrimidines

    KW - HUMAN O-6-ALKYLGUANINE-DNA ALKYLTRANSFERASE

    KW - INHIBITION

    KW - ANALOGS

    M3 - Article

    SP - 255

    EP - 258

    JO - Synlett

    JF - Synlett

    SN - 0936-5214

    IS - 2

    ER -