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

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Contents Vol 63(5)

doi:10.1071/CH09607

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, Anna P. Young ^C

^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





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Australian Journal of Chemistry 63(5) 785–791 http://dx.doi.org/10.1071/CH09607
Submitted: 24 November 2009 Accepted: 15 January 2010 Published online: 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.