Construction of Tetrazole Derivatives via Sequential Ugi‐N₃/Pd‐Catalyzed Isocyanide Insertion Reactions

Abstract

Herein, a straightforward method for the construction of tetrazole derivatives has been achieved through Pd-catalyzed isocyanide insertion reactions, which is a good extension for the response of multi-molecule isocyanides. The Ugi-N 3 reaction was introduced to the transformation to enrich the diversity of skeleton structures. The commercially available starting materials and moderate to good yields make this method a valuable tool for generating N-containing heterocyclic compounds.

Solvent-involved synthesis of pyrrolidin-5-one-2-carboxamides via a sequential Ugi/olefination reaction

“…The post-Ugi reactions are well suited for the construction of important heterocycles, macrocycles, and other compounds in drug discovery and natural product synthesis. 12 In continuation of our interest in reactions involving sulfur ylides and Ugi reactions, 13 we envisaged challenging the universal reactivity of sulfur ylides toward carbonyl derivatives. To our delight, an unexpected tandem Ugi/olefination reaction of (carboxymethyl)dimethylsulfonium bromide, aryl glyoxal, amines and isocyanides was observed to afford pyrrolidin-5-one-2-carboxamides with solvent participation, and (carboxymethyl)dimethylsulfonium bromide and aryl glyoxal facilitate the formation of double bonds in this reaction (Fig.…”