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

Maria Ines Flores-Conde 1 email, Leonor Reyes 1 email, Rafael Herrera 2 email, Hulme Rios 3 email, Miguel A. Vazquez 4,* email, Rene Miranda 3 email, Joaquin Tamariz 1 email and Francisco Delgado 1,* email
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; in revised form: 29 January 2012 / Accepted: 13 February 2012 / Published: 24 February 2012
PDF Full-text Download PDF Full-Text [461 KB, Updated Version, uploaded 27 February 2012 17:22 CET]
The original version is still available [482 KB, uploaded 24 February 2012 13:51 CET]
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.
Keywords: Diels-Alder cycloadditions; regioselectivity; Knoevenagel; infrared irradiation

Supplementary Files

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

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.

AMA Style

Flores-Conde MI, Reyes L, Herrera R, Rios H, Vazquez MA, 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. International Journal of Molecular Sciences. 2012; 13(3):2590-2617.

Chicago/Turabian Style

Flores-Conde, Maria Ines; Reyes, Leonor; Herrera, Rafael; Rios, Hulme; Vazquez, Miguel A.; Miranda, Rene; Tamariz, Joaquin; Delgado, Francisco. 2012. "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. 13, no. 3: 2590-2617.

Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert