7th International Conference on Multicomponent Reactions and Related Chemistry - Trifluoroethanol Induces a Novel Five Component Reaction: Synthesis of 4-imidazolidinone Derivatives.

Congreso

Resumen *

It is well known that a multi-component reaction (MCR) may be tuned by adapting the reaction conditions in order to generate different molecular scaffolds from the same starting materials.1 For example, depending on the catalyst, solvent, or heating mode, the same component may react via different pathways to produce different scaffolds. While optimizing the conditions for the well-known Ugi-Smile reaction, we came across an unexpected result: when trifluoroethanol was used as solvent, a 4-imidazolidinone 1 was obtained instead of the desired product. In this context, we found a novel five component reaction which we have dubbed as the ARG-5CR, and which involves an isocyanide, a primary amine, two molecules of formaldehyde and water as an acid component. In this work we describe the optimization of the reaction conditions and the scope of the procedure, which gave a good yield of the target compounds when a diverse set of alkylamines -both linear and branched- as well as functionalized amines and anilines were used. In the same way, a variety of isocyanides also reacted to render the corresponding imidazolidinones. Furthermore, as the procedure can be improved by generating the isocyanides in situ, thus avoiding the isolation of these ill-famed reactants2,3, this new MCR becomes a valuable and faster alternative for the synthesis of this family of heterocycles when compared to the methods reported4?7. Información suministrada por el agente en SIGEVA