Current studentsExisting staffContact us
 

N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIII.∗Cleavage and Rearrangement Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine 1,1-Dioxides

Simple item page
dc.contributor.authorNorman, R.
dc.contributor.authorPerkins, M.
dc.contributor.authorLiepa, A.
dc.contributor.authorFrancis, C.L.
dc.date.issued2016
dc.description.abstractTreatment of pyrazolo[1,5-b][1,2,4,6]thiatriazines 1 with the Vilsmeier-Haack reagent afforded pyrazolo[1,5-a][1,3,5]triazines 5. Reaction of compounds 1 with trifluoroacetic anhydride, dimethyl sulfoxide, and triethylamine afforded 5-dimethylsulfanylidene derivatives 8. The guanidino-pyrazole-sulfonic acid 9 was produced from treatment of compounds 1 with trifluoroacetic acid under anhydrous conditions. Similar treatment in the presence of water afforded the desulfonated pyrazolo-guanidine 6. Reactions of 6 with one-carbon electrophiles provided various 4-substituted pyrazolo[1,5-a][1,3,5]triazines 5. Attempted catalytic hydrogenolysis of N7-benzyl pyrazolo[1,5-b][1,2,4,6]thiatriazines 2 in alcohols led to sulfamates 12 from thiatriazine ring cleavage. Ethyl acetate or tert-butanol as solvent allowed successful debenzylation to provide compounds 1. Aminolysis of compounds 2 gave sulfamides 13. Thermal rearrangement of compounds 2 afforded 6-benzyl-pyrazolo[3,4-e][1,2,4]thiadiazines 14.
dc.identifier.citationAustralian Journal of Chemistry, 2016; 69(1):61-75
dc.identifier.doi10.1071/ch15445
dc.identifier.issn0004-9425
dc.identifier.issn1445-0038
dc.identifier.orcidNorman, R. [0000-0002-3118-3896]
dc.identifier.urihttps://hdl.handle.net/11541.2/36253
dc.language.isoen
dc.publisherCSIRO Publishing
dc.rightsCopyright CSIRO 2016
dc.source.urihttps://doi.org/10.1071/CH15445
dc.subjectRearrangement Reactions
dc.subjectChlorosulfonyl Chloroformamidines
dc.subjectcompounds
dc.titleN,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIII.∗Cleavage and Rearrangement Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine 1,1-Dioxides
dc.typeJournal article
pubs.publication-statusPublished
ror.mmsid9916800110201831

Files

Collections