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Int. J. Mol. Sci. 2012, 13(3), 2590-2617; doi:10.3390/ijms13032590
Article

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

1
, 1
, 2
, 3
, 4,* , 3
, 1
 and 1,*
1 Department of Organic Chemistry, National School of Biological Sciences, National Polytechnic Institute, Prol. Carpio y Plan de Ayala, S/N, 11340 Mexico, D. F., Mexico 2 Institute of Chemical-Biology Research, University of Michoacan of San Nicolás de Hidalgo, Edif. B-1, Ciudad Universitaria, Francisco J. Mujica S/N, 58066 Morelia, Mich, Mexico 3 Department of Chemical Sciences, Graduate School of Cuautitlán-National University of Mexico, Campo 1, Avenida 1ro. de Mayo S/N, Cuautitlán Izcalli, Estado de México 54740, Mexico 4 Department of Chemistry, University of Guanajuato, Noria Alta, S/N, Guanajuato Gto. 36050, Mexico
* Authors to whom correspondence should be addressed.
Received: 15 December 2011 / Revised: 29 January 2012 / Accepted: 13 February 2012 / Published: 24 February 2012
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Abstract

Infrared irradiation promoted the Diels-Alder cycloadditions of exo-2-oxazolidinone dienes 13 with the Knoevenagel adducts 46, as dienophiles, leading to the synthesis of new 3,5-diphenyltetrahydrobenzo[d]oxazol-2-one derivatives (7, 9, 11 and 1317), 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 1316 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.
Keywords: Diels-Alder cycloadditions; regioselectivity; Knoevenagel; infrared irradiation Diels-Alder cycloadditions; regioselectivity; Knoevenagel; infrared irradiation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Flores-Conde, M.I.; Reyes, L.; Herrera, R.; Rios, H.; Vazquez, M.A.; Miranda, R.; Tamariz, J.; Delgado, F. Highly Regio- and Stereoselective Diels-Alder Cycloadditions via Two-Step and Multicomponent Reactions Promoted by Infrared Irradiation under Solvent-Free Conditions. Int. J. Mol. Sci. 2012, 13, 2590-2617.

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