N,N-Dialkyl (N′-Chlorosulfonyl)chloroformamidines in Heterocyclic Synthesis. I. The Preparation of [1,2,3,5]Thiatriazole and [1,3,2,4]Oxathiadiazole Derivatives

Gary D. Fallon; Saba Jahangiri; Andris J. Liepa; Ruth C. J. Woodgate

doi:10.1071/CH04295

RESEARCH ARTICLE

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N,N-Dialkyl (N′-Chlorosulfonyl)chloroformamidines in Heterocyclic Synthesis. I. The Preparation of [1,2,3,5]Thiatriazole and [1,3,2,4]Oxathiadiazole Derivatives

Gary D. Fallon ^A , Saba Jahangiri ^B , Andris J. Liepa ^B ^C and Ruth C. J. Woodgate ^B

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, Monash University, Clayton VIC 3800, Australia.

^B CSIRO Molecular Science, Clayton South VIC 3169, Australia.

^C Corresponding author. Email: andy.liepa@csiro.au

Australian Journal of Chemistry 58(5) 332-338 https://doi.org/10.1071/CH04295
Submitted: 16 December 2004 Accepted: 23 March 2005 Published: 1 May 2005

Abstract

N,N-Dialkyl (N′-chlorosulfonyl)chloroformamidines 1 react regiospecifically with hydrazine derivatives to give [1,2,3,5]thiatriazole dioxides. Reaction of 1 with hydroxamic acids and N-methyl hydroxylamine gave derivatives of [1,3,2,4]oxathiadiazole dioxide 7, a new heterocycle.

Acknowledgments

We thank E. I. DuPont de Nemours and Co., Agricultural Products Department, for the biological screening of these compounds. We also thank Ms Katarina Johansson for technical assistance.

References

N,N-Dialkyl (N′-Chlorosulfonyl)chloroformamidines in Heterocyclic Synthesis. I. The Preparation of [1,2,3,5]Thiatriazole and [1,3,2,4]Oxathiadiazole Derivatives

Abstract

Acknowledgments

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