N,N-dialkyl-N'-chlorosulfonyl chloroformamidines in heterocyclic synthesis. Part VIII. Novel pyrazolo-fused oxathiadiazines and thiatriazoles

Craig Macdonald Forsyth, Craig L Francis, Saba Jahangiri, Andris J Liepa, Michael V Perkins, Anna P Young

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N,N-dialkyl-N -chlorosulfonyl chloroformamidines 1 reacted with pyrazol-3-ones 2 tunder 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[3,2b][ 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
Issue number4
Publication statusPublished - 2010

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