Synthesis of Fused Bicyclic [1,2,3]-Triazoles from γ-Amino Diazoketones

Abstract

Triazoles are an important class of N-heterocycles that are well known for their broad biological activities. In this work, we would like to demonstrate a direct synthesis of the rare fused bicyclic [1,2,3]-triazoles, employing γ-N-protected amino diazoketones as useful synthetic platforms. The strategy was based on the deprotection of a trifluoroacetamide group for the intramolecular and in situ generation of an α-diazo imine intermediate, followed by a 5-endo-dig cyclization to construct the bicyclic unit. In this fashion, the synthesis of a series of fused bicyclic [1,2,3]-triazoles could be carried out in good to excellent yields (63–95%).