α-Diazo-β-oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines

Alexander Safrygin, Dmitry Dar'in, Grigory Kantin, Mikhail Krasavin

    Research output: Contribution to journalArticlepeer-review

    7 Scopus citations

    Abstract

    The readily available α-diazo-β-oxosulfones have been employed, for the first time, in the Wolff cyclocondensation with aromatic amines promoted by 1.5-fold excess of TiCl4. The reaction was found to be general (as illustrated by 15 product examples) and resulted in moderate yields of medicinally relevant sulfonyl 1,2,3-triazoles. Excluding the Lewis acid promoter resulted in a clean and high-yielding formation of α-sulfonyl acetanilides resulting from the thermal Wolff rearrangement and trapping of the ketene intermediate with an aniline molecule.

    Original languageEnglish
    Pages (from-to)4721-4724
    Number of pages4
    JournalEuropean Journal of Organic Chemistry
    Volume2019
    Issue number29
    DOIs
    StatePublished - 7 Aug 2019

    Scopus subject areas

    • Physical and Theoretical Chemistry
    • Organic Chemistry

    Keywords

    • Triazoles
    • Wolff cyclocondensation
    • Wolff rearrangement
    • α-Diazo-β-oxosulfones
    • α-Sulfonyl acetanilides
    • alpha-Sulfonyl acetanilides
    • alpha-Diazo-beta-oxosulfones
    • CYCLOCONDENSATION

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