Reduction of different electron-poor N-heteroarylhydrazines in strong basic conditions.
The first application of the Wolff-Kishner reduction methodology to electron-poor heteroaromatic compounds is reported. Hydrazino-containing heterocycles with hydrazone-type tautomery have been reduced under basic conditions. This novel chemistry was successfully applied to mono-dehalogenate a number of electron-poor heterocycles in a regioselective manner. According to the experimental results, this reductive process is a base-catalyzed reaction that takes only place in the presence of air, probably through an oxygen-assisted mechanism. As consequence of the specific features of this kind of hydrazone/enehydrazine tautomers, the overall outcome of the process is the synthesis of a Shapiro-type reduction product by simply using a milder version of the Huang-Minlon methodology.
Unciti-Broceta
Asier
A
School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, UK. asier.ub@ed.ac.uk
Pineda de las Infantas
María J
MJ
Gallo
Miguel A
MA
Espinosa
Antonio
A
D004583:Electrons; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006834:Hydrazines / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry
D006571:Heterocyclic Compounds; D006834:Hydrazines; D006835:Hydrazones; D010100:Oxygen