Azide-Alkyne cyclization reactions for synthesis of new 1,2,3- triazole derivatives possessing highly substituted imidazoles

Triazole and its derivatives are a group of organic compounds with important biological activities including anti-cancer, anti-AIDS, anti-malaria and anti-bacteria agents. They have also other wide applications in industry, agriculture and especially in the field of drug discovery [1,2]. Hence, the synthesis of these azoles has been in the center of attention formany years.The purpose of this research, is the synthesis of new derivatives of 1,2,3- triazoles containing polysubstituted imidazole rings. The polyaromatic imidazoles were prepared by four-component reactions of aryl aldehydes, diketone (benzil), 4-aminophenol and ammonium acetatein the presence ofp-toluene sulfonic acid catalyst.All synthesized imidazoles have a hydroxy group whichwere converted into propargyl ether within treatment with propargyl chloride in the presence of a base. Propargyl etherswere used as terminal acetylenes in copper catalysed 1,3-dipolar cycloaddition reactions with benzyl azid to give the target triazole derivatives (figure 1).