Azidoisocyanides, New Bifunctional Reagents for Multicomponent Reactions and Biomolecule Modifications

The synthetic capabilities of chiral α,β-azidoisocyanides were systematically reviewed. The potential of using them as bifunctional building blocks for multicomponent Passerini and Ugi reactions and also for Cu(I)-catalyzed [3+2]-cycloaddition to form 1,2,3-triazoles was demonstrated. The bifunctional nature of these compounds enabled the development of a methodology for preparing peptides containing an azide group and conjugating them subsequently with various biologically active compounds containing an ethynyl group for targeted modification of biomolecules.