Resumen

MONROY-FLORES, Gustavo A. et al. Regioselective Functionalization and Diels-Alder Cycloadditions of Exocyclic Dienes in Five-membered Heterocycles. J. Mex. Chem. Soc [online]. 2025, vol.69, n.4, pp.709-730.  Epub 09-Mar-2026. ISSN 1870-249X.  https://doi.org/10.29356/jmcs.v69i4.2343.

An acid-catalyzed regioselective addition of diverse nucleophiles to exo-oxazolidin-2-one dienes was presently carried out, leading to a series of functionalized 4-oxazolin-2-ones. The direct formylation of 4-methyl-4-oxazolin-2-ones provided the corresponding 5-formyl-4-oxazolin-2-ones, which were applied in the construction of the 4,5-dihydrobenzo[d]oxazolones through a Staunton-Weinreb annulation process. The reactivity of symmetrical and unsymmetrical exo-imidazolidin-2-one dienes was studied in Diels-Alder cycloadditions with dienophiles N-phenylmaleimide and benzyne. The aromatization of the [4+2] adducts led to the polycyclic benzo- and naphtho[d]imidazol-2-ones, which have potential pharmacological activity.

Palabras llave : 4,5-dimethylene-2-oxazolidinone dienes; 5-functionalized 4-oxazolin-2-ones; 4,5-dimethylene-2-imidazolidinone dienes; Staunton-Weinreb annulation; Diels-Alder reaction.

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