Synthesis of Functionalized 1<i>H</i>-Imidazoles via Denitrogenative Transformation of 5-Amino-1,2,3-Triazoles

Abstract

An efficient access to novel 2-substituted 1H-imidazole derivatives was developed based on acid-mediated denitrogenative transformation of 5-amino-1,2,3-triazole derivatives available through dipolar azide−nitrile cycloaddition (DCR). The proposed approach includes intramolecular cyclization of 5-amino-4-aryl-1-(2,2-diethoxyethyl) 1,2,3-triazoles followed by triazole ring opening and insertion of in situ formed carbene intermediate into the O-H bond of different alcohols under acidic conditions.

Keywords

• imidazoles
• 5-amino-1,2,3-triazoles
• denitrogenative transformation
• pyridotriazoles