Direct C(sp ² )‐H Cyanation of Imidazole N‐Oxides in the Synthesis of Nitrile and Amide Derivatives

ABSTRACT The nucleophilic substitution of hydrogen (S N H ) reaction was successfully applied as an original approach for the non‐catalytic C─H cyanation of both non‐aromatic 2 H ‐ and novel aromatic 1 H ‐imidazoles 1‐oxides. A series of new carbonitrile‐containing azaheterocyclic derivatives were synthesized in good yields of 61%–93% using trimethylsilyl cyanide (TMSCN) as the CN‐group source. Further modification of the nitrile group was achieved via the Radziszewski reaction for the synthesis of carboxamides of diverse architectures in yields ranging from 82% to 91%. The obtained compounds could be utilized as synthons for the subsequent chemical transformations focused on the design of pharmacologically active compounds and functional materials.