A New Approach for the Synthesis of <i>N</i>-Arylamides Starting from Benzonitriles

Abstract

N-Arylamides are a ubiquitous component of a broad range of natural products and biologically active compounds. In this paper, a new synthetic protocol for the preparation of N-arylamides was developed via the hypervalent iodine-mediated aza-Hofmann-type rearrangement of amidines. The reaction proceeded smoothly at 100 °C in the presence of PhINTs in toluene solvent. The requisite amidine substrates were prepared from amines and nitriles by applying the Pinner reaction approach. Considering the easy access of amidines from nitriles, the overall process is the conversion of nitriles to acetanilide and N-arylamides. As an application of the protocol, the preparation of paracetamol from 4-cyanophenol is also described.

Keywords

• <i>N</i>-arylamides
• nitriles
• amidines
• paracetamol