Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.

FAILLACE, MARTIN SEBASTIAN; CEBALLOS, NOELIA MARCELA; SHUSTOVA, NATALIA; PELÁEZ, WALTER JOSÉ

Asian Journal of Organic Chemistry

Wiley

Lugar: New York; Año: 2023

2193-5807

In this work, we report the regiospecific and stereoselective synthesis of novel pyrrolo thioxoimidazolidinones withpromising biological activities due to the inherent pharmaceutical properties of thioxoimidazolidinone core. Thereaction of different thioxoimidazolidinones with trans-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (ETFBO) yieldsbicyclic 1,3-diaza heterocycles bearing the trifluoromethyl (CF3) moiety. Our investigation involved both depthexperimental analysis and theoretical calculations to fathom out the mode of reaction of this building block andelucidate the underlying mechanism operating for the observed reactions. Remarkably, this unusual mechanismretained the ethanol moiety from the building block in the final products, deviating from conventional nucleophilicreactions reported in the literature