Hypervalent Iodine(III)‐Mediated Regioselective Cyanation of Quinoline N‐Oxides with Trimethylsilyl Cyanide

Abstract A regioselective cyanation of quinoline N ‐oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal‐free and base‐free reaction conditions to obtain 2‐cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N−O bond cleavage. The reaction system featured a wide range of substrate suitability and high yields. The procedure was enlarged gram‐scale to synthesize the tuberculosis (TB) inhibitor. Finally, according to some experimental results, a plausible mechanism for the cyanation reaction is proposed. magnified image