Introduction While looking for some appropriate research projects, I had been impressed by and interested in the work of Danishefsky' and others' regarding the use of "Eschen-moser's salt" (1). During the course of a l~terature search on an industrial project, we came across an article by Gold,' which described the preparation of a rather interesting vinylogous iminium salt (2). The name assign...

A very simple annulation reaction was designed, allowing an imidazole moiety to be fused onto a range of pyridine-based derivatives. The methodology consists of an activation step via the formation of a pyridinium salt to increase the electrophilicity of the pyridine ring, followed by a cascade reaction triggered by a nucleophilic attack of the iminium moiety. Depending on the pyridinium salt, ...

Owing to their various modes of reactivity, aaminonitriles represent versatile building blocks for the construction of a wide range of nitrogen heterocycles. The present Concept article focuses on synthetic methodologies using their bifunctional nature which is the basis of their reactivity as a-amino carbanions and as iminium ions. Reactions exclusively taking place on either the amine or on t...

We describe a new 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU)-mediated coupling reaction to produce 2-imino benzo[e]-1,3-oxazin-4-ones from salicylic acids and anilines. Mechanistic studies support a reaction pathway in which HATU mediates carbon transfer to the initially formed salicylanilides to form in succession reactive tetramethyli...

The development of a performant aminated catalyst for aldol condensations requires the combined tuning active site, support and solvent system. For this purpose, pyrrolidine group was immobilized on swellable polymer resin. Favorable interactions between water (in its role as solvent) resulted in turnover frequency (TOF) amounting to 3.0 ± 1.5 × 10−3 s−1, despite potential inhibition sites by f...