Abstract
We have encountered a superbase‐mediated chemoselective reaction of N‐tosylhydrazones with aza‐ortho‐quinone methide precursors. When tosylhydrazone was treated with ortho‐aminobenzyl alcohol in super basic conditions (KOH+DMSO), we observed the formation of 2‐substituted quinoline. The reaction was found to be general, and by this method, mono‐, di‐ and tri‐substituted quinolines could be made. We could prove experimentally and theoretically that the reaction proceeded via the formation of an azine from the basic decomposition of N‐tosylhydrazones. Finally, the reaction of tosylhydrazone with N‐(2‐(chloromethyl) phenyl)‐4‐methylbenzenesulfonamide (aza‐ortho‐quinone methide precursor) under super basic conditions afforded hydrazine substituted sulfonamides.
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