Affiliation:
1. Chemical Sciences and Technology Division CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST) 695019 Thiruvananthapuram India
2. Academy of Scientific and Innovative Research (AcSIR) 201002 Ghaziabad India
3. Research and Post-Graduate Department of Chemistry St. Joseph's College (Autonomous) Devagiri 673008 Calicut India
Abstract
AbstractWe 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.