Pyrazoline ring formation. Part I. The action of phenylhydrazine on some saturated and unsaturated β-amino-ketones

H B Nisbet

    Research output: Contribution to journalArticle

    Abstract

    Phenylhydrazine, acting on ß-sec.-aminoethyl ketones in the form of their hydrochlorides, gives first the phenylhydrazone, which by extrusion of a sec.-base residue yields a pyrazoline derivative. Examination of the possible reaction mechanisms suggests the intermediate formation of a vinyl derivative which undergoes prototropic rearrangement to the pyrazoline. The phenylhydrazones of a-unsaturated ß-sec.-aminoethyl ketone hydrochlorides on treatment with acid yield in the main 3-ß-sec.- aminoethylpyrazolines. In addition, however, by extrusion of a sec.-base residue certain styryl and substituted styryl ketone phenylhydrazones of this type have been shown to yield minute quantities of 1 : 5-diphenyl-3-vinylpyrazoline derivatives. The formation of the phenylhydrazones of styryl vinyl ketones as intermediates is postulated.

    LanguageEnglish
    Pages126-129
    Number of pages4
    JournalJournal of the Chemical Society (Resumed)
    Publication statusPublished - 1945

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    Ketones
    Derivatives
    Extrusion
    Acids
    phenylhydrazone
    phenylhydrazine

    Cite this

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    abstract = "Phenylhydrazine, acting on {\ss}-sec.-aminoethyl ketones in the form of their hydrochlorides, gives first the phenylhydrazone, which by extrusion of a sec.-base residue yields a pyrazoline derivative. Examination of the possible reaction mechanisms suggests the intermediate formation of a vinyl derivative which undergoes prototropic rearrangement to the pyrazoline. The phenylhydrazones of a-unsaturated {\ss}-sec.-aminoethyl ketone hydrochlorides on treatment with acid yield in the main 3-{\ss}-sec.- aminoethylpyrazolines. In addition, however, by extrusion of a sec.-base residue certain styryl and substituted styryl ketone phenylhydrazones of this type have been shown to yield minute quantities of 1 : 5-diphenyl-3-vinylpyrazoline derivatives. The formation of the phenylhydrazones of styryl vinyl ketones as intermediates is postulated.",
    author = "Nisbet, {H B}",
    year = "1945",
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    journal = "Journal of the Chemical Society (Resumed)",
    issn = "0368-1769",
    publisher = "Chemical Society",

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    T1 - Pyrazoline ring formation. Part I. The action of phenylhydrazine on some saturated and unsaturated β-amino-ketones

    AU - Nisbet, H B

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    N2 - Phenylhydrazine, acting on ß-sec.-aminoethyl ketones in the form of their hydrochlorides, gives first the phenylhydrazone, which by extrusion of a sec.-base residue yields a pyrazoline derivative. Examination of the possible reaction mechanisms suggests the intermediate formation of a vinyl derivative which undergoes prototropic rearrangement to the pyrazoline. The phenylhydrazones of a-unsaturated ß-sec.-aminoethyl ketone hydrochlorides on treatment with acid yield in the main 3-ß-sec.- aminoethylpyrazolines. In addition, however, by extrusion of a sec.-base residue certain styryl and substituted styryl ketone phenylhydrazones of this type have been shown to yield minute quantities of 1 : 5-diphenyl-3-vinylpyrazoline derivatives. The formation of the phenylhydrazones of styryl vinyl ketones as intermediates is postulated.

    AB - Phenylhydrazine, acting on ß-sec.-aminoethyl ketones in the form of their hydrochlorides, gives first the phenylhydrazone, which by extrusion of a sec.-base residue yields a pyrazoline derivative. Examination of the possible reaction mechanisms suggests the intermediate formation of a vinyl derivative which undergoes prototropic rearrangement to the pyrazoline. The phenylhydrazones of a-unsaturated ß-sec.-aminoethyl ketone hydrochlorides on treatment with acid yield in the main 3-ß-sec.- aminoethylpyrazolines. In addition, however, by extrusion of a sec.-base residue certain styryl and substituted styryl ketone phenylhydrazones of this type have been shown to yield minute quantities of 1 : 5-diphenyl-3-vinylpyrazoline derivatives. The formation of the phenylhydrazones of styryl vinyl ketones as intermediates is postulated.

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    M3 - Article

    SP - 126

    EP - 129

    JO - Journal of the Chemical Society (Resumed)

    T2 - Journal of the Chemical Society (Resumed)

    JF - Journal of the Chemical Society (Resumed)

    SN - 0368-1769

    ER -