3739-70-6Relevant academic research and scientific papers
5-Morpholino-1,2,3,4-thiatriazole as a sulfur-transfer reagent in the reactions with thioketones
Mloston, Grzegorz,Woznicka, Marta,Heimgartner, Heinz
, p. 594 - 600 (2007)
The thermal decomposition of 5-morpholino-1,2,3,4-thiatriazole (7), which leads to the extrusion of an active form of sulfur, in the presence of different thioketones is described. The interception of the S-atom by the C=S bond leads to in situ formation of an elusive thiocarbonyl S-sulfide of type 5. This intermediate is a prone 1,3-dipole, which undergoes effectively [2 + 3] cycloadditions with thioketones to yield 1,2,4-trithiolane derivatives in a regioselective manner. Unexpectedly, 3,3-dichloro-2,2,4,4-tetramethyl-3- thioxocyclobutanone (1c) does not lead to the expected symmetrical 1,2,4-trithiolane. This result can be explained by the reduced stability of the corresponding thiosulfine 5c. Three-component reactions, which were carried out in the presence of equimolar amounts of two different thioketones, result in the formation of 'mixed' 1,2,4-trithiolanes of type 8.
An efficient protocol for the formation of aminothiatriazoles from thiocarbamoylimidazolium salts
Ponzo, Marisa G,Evindar, Ghotas,Batey, Robert A
, p. 7601 - 7604 (2007/10/03)
A new protocol for the formation of substituted aminothiatriazoles from thiocarbamoylimidazolium salts is outlined. Thiocarbamoylimidazolium salts are synthesized from the corresponding amines by treatment with thiocarbonyldiimidazole (TCDI) followed by methylation with iodomethane. Thiocarbamoylimidazolium salts are shown to act as thiocarbamoyl cation equivalents. Substitution of the salts by azide anion followed by electrocyclization affords substituted aminothiatriazoles in good to excellent yields.
