N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part VII* 4-Dialkylamino[1,2,3,5]Benzoxathiadiazepine Dioxides and 4-Dialkylamino-[2,1,3,5]Benzothiatriazepine Dioxides

Teresa Cablewski; Craig M. Forsyth; Craig L. Francis; Andris J. Liepa; Victor Tran

doi:10.1071/CH08250

RESEARCH ARTICLE

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N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part VII^* 4-Dialkylamino[1,2,3,5]Benzoxathiadiazepine Dioxides and 4-Dialkylamino-[2,1,3,5]Benzothiatriazepine Dioxides

Teresa Cablewski ^A , Craig M. Forsyth ^B , Craig L. Francis ^A ^C , Andris J. Liepa ^A and Victor Tran ^A

+ Author Affiliations

- Author Affiliations

^A CSIRO Molecular and Health Technologies, Clayton, Vic. 3168, Australia.

^B School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.

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

Australian Journal of Chemistry 61(10) 785-796 https://doi.org/10.1071/CH08250
Submitted: 10 June 2008 Accepted: 31 July 2008 Published: 6 October 2008

Abstract

N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted with 2-aminophenols 2 to give 4-dialkylamino[1,2,3,5]benzoxathiadiazepine dioxides 3, which are examples of a new ring system. Reaction of 1 with 1,2-diaminobenzenes 7 afforded 4-dialkylamino[2,1,3,5]benzothiatriazepine dioxides 8 and 9, which are new derivatives of a rare ring system. Some N-alkyl and N-acyl derivatives of 3 and 8 were prepared to demonstrate the potential of these compounds as novel scaffolds for synthetic and medicinal chemistry.

^* Part VI, Aust. J. Chem. 2008, 61, 332.

Acknowledgements

We thank Dr Roger Mulder and Dr Jo Cosgriff for assistance with NMR spectroscopy, and Mr Carl Braybrook for assistance with mass spectrometry.

References

N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part VII* 4-Dialkylamino[1,2,3,5]Benzoxathiadiazepine Dioxides and 4-Dialkylamino-[2,1,3,5]Benzothiatriazepine Dioxides

Abstract

Acknowledgements

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N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part VII^* 4-Dialkylamino[1,2,3,5]Benzoxathiadiazepine Dioxides and 4-Dialkylamino-[2,1,3,5]Benzothiatriazepine Dioxides