NDLI: Highly Regio- and Stereoselective Diels-Alder Cycloadditions via Two-Step and Multicomponent Reactions Promoted by Infrared Irradiation under Solvent-Free Conditions

Content Provider	MDPI
Author	Flores-Conde, Maria Ines Reyes, Leonor Herrera, Rafael Rios, Hulme Vazquez, Miguel A. Miranda, Rene Tamariz, Joaquin Delgado, Francisco
Abstract	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.
File Size	472064
Ending Page	2617
Page Count	28
Starting Page	2590
File Format	PDF
e-ISSN	14220067
DOI	10.3390/ijms13032590
Journal	International Journal of Molecular Sciences
Issue Number	3
Volume Number	13
Language	English
Publisher Date	2012-02-24
Access Restriction	Open
Subject Keyword	Diels-Alder cycloadditions regioselectivity Knoevenagel infrared irradiation
Content Type	Text
Resource Type	Article

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Highly Regio- and Stereoselective Diels-Alder Cycloadditions via Two-Step and Multicomponent Reactions Promoted by Infrared Irradiation under Solvent-Free Conditions