Transition Metal-Free,Base-Induced Arylation of Amino Acids: Synthesis of N-(para-Substituted phenyl)amino-2-carboxylic acids

摘要

A metal-free aryl amination reaction of aryl halides and amino acids;with the amino acid serving as the nucleophilic aminating agent,is reported.The reaction was achieved by the condensation of various aryl halides 1 with cyclic and acyclic amino acids 2,in the presence of a cheap and readily available base,potassium carbonate,in refluxing ethanol/water solution(1 : 1)for 3 h,under simple operating conditions.The products,N-(p-substituted phenyl)-amino-2-carboxylic acids 3–12,were obtained in isolated yields of 25–90% and characterized by IR,~1H-and ~(13)C-NMR spectroscopy and high-resolution mass spectrometry.These arylated amino acids are vital synthons and precursors to many compounds of physiological importance.