N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part IX.* Novel Triazolo-Fused Thiatriazoles and Pyrazolo-Fused Oxathiazines

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

doi:10.1071/CH09607

RESEARCH FRONT

N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part IX.* Novel Triazolo-Fused Thiatriazoles and Pyrazolo-Fused Oxathiazines

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(5) 785-791 https://doi.org/10.1071/CH09607
Submitted: 24 November 2009 Accepted: 15 January 2010 Published: 21 May 2010

Abstract

N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted with 4-substituted urazoles 2 to give [1,2,4]triazolo[1,2-b][1,2,3,5]thiatriazoles 3 in a selective 1,2-NN dinucleophilic mode of reaction. The reaction of 1 with N ¹-substituted pyrazol-5-ones 4 afforded pyrazolo[4,3-e][1,4,3]oxathiazines 5 via selective 1,3-CCO dinucleophilic substitution. Compounds 3 and 5 were the sole products isolated from the respective reactions and both represent new ring systems.

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 VIII, published in Aust. J. Chem. 2010, 63, 659.

N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part IX.* Novel Triazolo-Fused Thiatriazoles and Pyrazolo-Fused Oxathiazines

Abstract

Acknowledgements

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