Highly regio- and Stereoselective Diels-Alder Cycloadditions Via Two-Step and Multicomponent Reactions Promoted by Infrared Irradiation Under Solvent-Free Conditions

Maria Ines Flores-Conde, Leonor Reyes, Rafael Herrera, Hulme Rios, Miguel A. Vazquez, Rene Miranda, Joaquin Tamariz, Francisco Delgado

Producción científica: Contribución a una revistaArtículorevisión exhaustiva

18 Citas (Scopus)

Resumen

Infrared irradiation promoted the Diels-Alder cycloadditions of exo-2-oxazolidinone dienes 1-3 with the Knoevenagel adducts 4-6, as dienophiles, leading to the synthesis of new 3,5-diphenyltetrahydrobenzo[d]oxazol-2-one derivatives (7, 9, 11 and 13-17), under solvent-free conditions. These cycloadditions were performed with good regio- and stereoselectivity, favoring the para-endo cycloadducts. We also evaluated the one-pot three-component reaction of active methylene compounds 20, benzaldehydes 21 and exo-2-oxazolidinone diene 2 under the same reaction conditions. A cascade Knoevenagel condensation/Diels-Alder cycloaddition reaction was observed, resulting in the final adducts 13-16 in similar yields. These procedures are environmentally benign, because no solvent and no catalyst were employed in these processes. The regioselectivity of these reactions was rationalized by Frontier Molecular Orbital (FMO) calculations.

Idioma originalInglés
Páginas (desde-hasta)2590-2617
Número de páginas28
PublicaciónInternational Journal of Molecular Sciences
Volumen13
N.º3
DOI
EstadoPublicada - mar. 2012

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