N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. IV. 3-Dialkylamino-1,1,8-trioxo-1H-1λ6-pyrano[3,4-e][1,4,3]oxathiazines

Teresa Cablewski; Craig L. Francis; Andris J. Liepa

doi:10.1071/CH06368

RESEARCH ARTICLE

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N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. IV. 3-Dialkylamino-1,1,8-trioxo-1H-1λ⁶-pyrano[3,4-e][1,4,3]oxathiazines

Teresa Cablewski ^A , Craig L. Francis ^A ^B and Andris J. Liepa ^A ^B

+ Author Affiliations

- Author Affiliations

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

^B Corresponding authors. Email: craig.francis@csiro.au; andy.liepa@csiro.au

Australian Journal of Chemistry 60(2) 113-119 https://doi.org/10.1071/CH06368
Submitted: 11 October 2006 Accepted: 27 November 2006 Published: 13 February 2007

Abstract

N,N-dialkyl-N′-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone derivatives 2 to give 3-dialkylamino-1,1,8-trioxo-1H-1λ⁶-pyrano[3,4-e][1,4,3]oxathiazines 3. Dichloride 1b reacted regioselectively with 1,3-dimethylbarbituric acid 10 to give 3-diethylamino-5,7-dimethyl-1,1,6,8-tetraoxo-1H-1λ⁶-pyrimido[5,4-e][1,4,3]oxathiazine 11. The compounds 3 and 11 are derivatives of new ring systems.

Acknowledgments

We thank Roger Mulder for assistance with NMR spectroscopy, Gary Fallon and Craig Forsyth (Monash University) for X-ray crystallography, and E. I. DuPont de Nemours and Co., Agricultural Products Department, for biological screening of these compounds.

References

N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. IV. 3-Dialkylamino-1,1,8-trioxo-1H-1λ6-pyrano[3,4-e][1,4,3]oxathiazines

Abstract

Acknowledgments

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N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. IV. 3-Dialkylamino-1,1,8-trioxo-1H-1λ⁶-pyrano[3,4-e][1,4,3]oxathiazines