N,N-Dialkyl-N'-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part VIII.* Novel Pyrazolo-Fused Oxathiadiazines and Thiatriazoles

Craig Forsyth, Craig Francis, Saba Jahangiri, Andris Liepa, Michael Perkins, Anna Young

    Research output: Contribution to journalArticle

    7 Citations (Scopus)

    Abstract

    N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted with pyrazol-3-ones 2 under a variety of conditions to give pyrazolo[2,3-e][1,2,3,5] oxathiadiazine dioxides 3 and pyrazolo[3,2-b][1,4,3,5]oxathiadiazine dioxides 5, and frequently, one or both of pyrazolo[1,2-b][1,2,3,5]thiatriazole 1,1,5-trioxides 4 and 1,1,7-trioxides 6. In all reactions, the pyrazolo[3,2-b][1,4,3,5]oxathiadiazine 5 was the major product, with the pyrazolo[2,3-e][1,2,3,5]oxathiadiazine 3 being a significant product in the absence of base. Prior to our recent work, the core ring systems of compounds 3 and 5 had not been reported and compounds 4 and 6 are new derivatives of a rare ring system.

    Original languageEnglish
    Pages (from-to)659-668
    Number of pages10
    JournalAustralian Journal of Chemistry
    Volume63
    Issue number4
    DOIs
    Publication statusPublished - 2010

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