N,N-Dialkyl-N′-Chlorosulfonylchloroformamidines in Heterocyclic Synthesis. II. Thiazolo-, Thiadiazolo-, and Oxadiazolo-Fused [1,2,4,6]Thiatriazine Dioxides
Gary D. Fallon A , Craig L. Francis B C , Katarina Johansson B , Andris J. Liepa B C and Ruth C. J. Woodgate BA School of Chemistry, Monash University, Clayton VIC 3800, Australia.
B CSIRO Molecular and Health Technologies, Clayton South VIC 3168, Australia.
C Corresponding authors. Email: craig.francis@csiro.au; andy.liepa@csiro.au
Australian Journal of Chemistry 58(12) 891-900 https://doi.org/10.1071/CH05070
Submitted: 4 March 2005 Accepted: 23 May 2005 Published: 20 December 2005
Abstract
N,N-dialkyl-N′-chlorosulfonylchloroformamidines 1 were treated with 2-aminothiazoline, 2-aminothiazoles, 2-aminobenzothiazoles, 2-amino-1,3,4-thiadiazoles, and 2-amino-1,3,4-oxadiazoles to give a 6,7-dihydrothiazolo[3,2-b][1,2,4,6]thiatriazine dioxide 3, a 6,7-dihydrothiazolo[2,3-c][1,2,4,6]thiatriazine dioxide 4, thiazolo[3,2-b][1,2,4,6]thiatriazine dioxides 5, [1,2,4,6]thiatriazino[3,2-b]benzothiazole dioxides 7, a [1,2,4,6]thiatriazino[3,4-b]benzothiazole dioxide 8, [1,3,4]thiadiazolo[2,3-c][1,2,4,6]thiatriazine dioxides 10, [1,3,4]thiadiazolo[3,2-b][1,2,4,6]thiatriazine dioxides 11, [1,3,4]oxadiazolo[2,3-c][1,2,4,6]thiatriazine dioxides 13, and [1,3,4]thiadiazolo[3,2-b][1,2,4,6]thiatriazine dioxides 14. Compounds 3, 4, 5, 7, 8, 10, 11, 13, and 14 are derivatives of new ring systems.
Acknowledgments
We thank Roger Mulder for assistance with NMR spectroscopy and E. I. DuPont de Nemours and Co., Agricultural Products Department, for the biological screening of these compounds.
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* Using freshly prepared dichloro compound 1a.
† Using freshly prepared dichloro compound 1d.
