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

Craig M. Forsyth; Craig L. Francis; Saba Jahangiri; Andris J. Liepa; Michael V. Perkins; Anna P. Young

doi:10.1071/CH09581

RESEARCH ARTICLE

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

Craig M. Forsyth ^A , Craig L. Francis ^B ^D , Saba Jahangiri ^B , Andris J. Liepa ^B , Michael V. Perkins ^C and Anna P. Young ^C

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, Monash University, Box 23, Clayton, Vic. 3800, Australia.

^B CSIRO Molecular and Health Technologies, Bag 10, Clayton South, Vic. 3169, Australia.

^C School of Chemistry, Physics and Earth Sciences, Flinders University, PO Box 2100, Adelaide, SA 5001, Australia.

^D Corresponding author. Email: craig.francis@csiro.au

Australian Journal of Chemistry 63(4) 659-668 https://doi.org/10.1071/CH09581
Submitted: 6 November 2009 Accepted: 10 December 2009 Published: 8 April 2010

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.

Acknowledgements

We thank Ms Katarina Johansson and Mrs Ruth Woodgate for technical assistance, Dr Roger Mulder and Dr Jo Cosgriff for assistance with NMR spectroscopy, and Mr Carl Braybrook and Dr Jo Cosgriff for mass spectrometry.

References

^* Part VII, Aust. J. Chem. 2008, 61, 785.

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

Abstract

Acknowledgements

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