Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide

T Niemi, J E Perea-Buceta, I Fernandez, Sami Alakurtti, Elina Rantala, T Repo (Corresponding Author)

    Research output: Contribution to journalArticleScientificpeer-review

    13 Citations (Scopus)

    Abstract

    The reaction of {\beta}- and {\gamma}-haloamines with carbon dioxide to give pharmaceutically relevant 2-oxazolidinones and 1,3-dioxazin-2-ones, was found to proceed efficiently in the presence of a base and in the absence of catalyst. After optimization of reaction conditions, the system was successfully expanded to a variety of haloamines, even at multigram scale. The reaction was further studied in silico by DFT calculations.
    Original languageEnglish
    Pages (from-to)8867-8871
    JournalChemistry - A European Journal
    Volume20
    Issue number29
    DOIs
    Publication statusPublished - 2014
    MoE publication typeA1 Journal article-refereed

    Fingerprint

    Oxazolidinones
    Discrete Fourier transforms
    Carbon Dioxide
    Carbon dioxide
    Catalysts

    Keywords

    • 2-oxazolidones
    • antibiotics
    • carbon dioxide activation
    • carbon dioxide fixation
    • density functional calculations

    Cite this

    Niemi, T., Perea-Buceta, J. E., Fernandez, I., Alakurtti, S., Rantala, E., & Repo, T. (2014). Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide. Chemistry - A European Journal, 20(29), 8867-8871. https://doi.org/10.1002/chem.201402368
    Niemi, T ; Perea-Buceta, J E ; Fernandez, I ; Alakurtti, Sami ; Rantala, Elina ; Repo, T. / Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 29. pp. 8867-8871.
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    abstract = "The reaction of {\beta}- and {\gamma}-haloamines with carbon dioxide to give pharmaceutically relevant 2-oxazolidinones and 1,3-dioxazin-2-ones, was found to proceed efficiently in the presence of a base and in the absence of catalyst. After optimization of reaction conditions, the system was successfully expanded to a variety of haloamines, even at multigram scale. The reaction was further studied in silico by DFT calculations.",
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    author = "T Niemi and Perea-Buceta, {J E} and I Fernandez and Sami Alakurtti and Elina Rantala and T Repo",
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    Niemi, T, Perea-Buceta, JE, Fernandez, I, Alakurtti, S, Rantala, E & Repo, T 2014, 'Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide', Chemistry - A European Journal, vol. 20, no. 29, pp. 8867-8871. https://doi.org/10.1002/chem.201402368

    Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide. / Niemi, T; Perea-Buceta, J E; Fernandez, I; Alakurtti, Sami; Rantala, Elina; Repo, T (Corresponding Author).

    In: Chemistry - A European Journal, Vol. 20, No. 29, 2014, p. 8867-8871.

    Research output: Contribution to journalArticleScientificpeer-review

    TY - JOUR

    T1 - Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide

    AU - Niemi, T

    AU - Perea-Buceta, J E

    AU - Fernandez, I

    AU - Alakurtti, Sami

    AU - Rantala, Elina

    AU - Repo, T

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    N2 - The reaction of {\beta}- and {\gamma}-haloamines with carbon dioxide to give pharmaceutically relevant 2-oxazolidinones and 1,3-dioxazin-2-ones, was found to proceed efficiently in the presence of a base and in the absence of catalyst. After optimization of reaction conditions, the system was successfully expanded to a variety of haloamines, even at multigram scale. The reaction was further studied in silico by DFT calculations.

    AB - The reaction of {\beta}- and {\gamma}-haloamines with carbon dioxide to give pharmaceutically relevant 2-oxazolidinones and 1,3-dioxazin-2-ones, was found to proceed efficiently in the presence of a base and in the absence of catalyst. After optimization of reaction conditions, the system was successfully expanded to a variety of haloamines, even at multigram scale. The reaction was further studied in silico by DFT calculations.

    KW - 2-oxazolidones

    KW - antibiotics

    KW - carbon dioxide activation

    KW - carbon dioxide fixation

    KW - density functional calculations

    U2 - 10.1002/chem.201402368

    DO - 10.1002/chem.201402368

    M3 - Article

    VL - 20

    SP - 8867

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    JO - Chemistry - A European Journal

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    Niemi T, Perea-Buceta JE, Fernandez I, Alakurtti S, Rantala E, Repo T. Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide. Chemistry - A European Journal. 2014;20(29):8867-8871. https://doi.org/10.1002/chem.201402368