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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.
Flores-Conde, Maria Ines; Reyes, Leonor; Herrera, Rafael; Rios, Hulme; Vazquez, Miguel A; Miranda, Rene; Tamariz, Joaquin; Delgado, Francisco.
Afiliação
  • Flores-Conde MI; 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.
  • Reyes L; 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.
  • Herrera R; 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.
  • Rios H; 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.
  • Vazquez MA; Department of Chemistry, University of Guanajuato, Noria Alta, S/N, Guanajuato Gto. 36050, Mexico.
  • Miranda R; 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.
  • Tamariz J; 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.
  • Delgado F; 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.
Int J Mol Sci ; 13(3): 2590-2617, 2012.
Article em En | MEDLINE | ID: mdl-22489113
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.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Reação de Cicloadição / Raios Infravermelhos Idioma: En Revista: Int J Mol Sci Ano de publicação: 2012 Tipo de documento: Article País de afiliação: México País de publicação: Suíça
Texto completo
Adicionar na Minha BVS
Imprimir
XML
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Reação de Cicloadição / Raios Infravermelhos Idioma: En Revista: Int J Mol Sci Ano de publicação: 2012 Tipo de documento: Article País de afiliação: México País de publicação: Suíça