343337-70-2Relevant academic research and scientific papers
N-Sulfonylcarboxamide as an Oxidizing Directing Group for Ruthenium-Catalyzed C–H Activation/Annulation
Petrova, Elina,Rasina, Dace,Jirgensons, Aigars
supporting information, p. 1773 - 1779 (2017/04/13)
N-Sulfonylcarboxamides can act as both a directing group for C–H activation and an internal oxidant in the Ru-catalyzed annulation reaction with alkynes to give isoquinolones. Of all of the N-sulfonylcarboxamides that were studied, the N-(2,6-difluorophenyl)sulfonamide derivatives were found to be the most efficient and led to the formation of an unstable sulfinate byproduct that decomposed into 1,3-difluorobenzene under the reaction conditions. The described isoquinolone synthesis provides an alternative to the currently known traceless annulations of hydroxamic acid and sulfoximine derivatives.
The aza Curtius rearrangement
Yagupolskii, Lev M.,Shelyazhenko, Svetlana V.,Maletina, Irina I.,Petrik, Vitalij N.,Rusanov, Eduard B.,Chernega, Alexander N.
, p. 1225 - 1233 (2007/10/03)
On interaction of N-(trifluoromethylsulfonyl)carboximidoyl chlorides (analogs of acyl chlorides in which the carbonyl oxygen atom is substituted by the more strongly electron-withdrawing =NSO2CF3 group) with sodium azide in glyme or acetonitrile at -5 to +10 °C, dinitrogen is eliminated quantitatively and carbodiimides RN=C=NSO2CF3 are formed in high yield. In other words, an aza Curtius rearrangement occurs. The carbodiimides react with water, alcohols, and secondary amines to give corresponding ureas, isoureas, and guanidine derivatives. Imidoyl chlorides with substituents other than SO2RF do not enter into the aza Curtius reaction.
