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Diels-Alder Reactions of 2-Oxazolidinone Dienes in Polar Solvents Using Catalysis or Non-conventional Energy Sources

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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

The (Z)-N-substituted 4-methylene-5-propylidene-2-oxazolidinone dienes were prepared by a one-step synthesis, starting from 2,3-hexanedione and isocyanates. Diels-Alder cycloadditions of these dienes were carried out in the presence of the dienophiles methyl vinyl ketone, methyl propiolate, and a captodative olefin, under conditions such as solvents of high polarity, Lewis acid catalysis, and non-conventional energy sources. The reactions carried out either with mixtures of H2O/MeOH or under BF3·Et2O catalysis yielded the highest regio- and stereoselectivities. The use of ionic liquids, microwaves, and ultrasound did not significantly increase the selectivity.

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Authors and Affiliations

  1. Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340, México, D.F., Mexico

    Aydeé Fuentes, Rafael Martínez-Palou, Hugo A. Jiménez-Vázquez, Francisco Delgado, Alicia Reyes & Joaquín Tamariz

  2. Programa de Ingeniería Molecular, Instituto Mexicano del Petróleo, Eje Lázaro Cárdenas 152, 07730, México, D.F., Mexico

    Rafael Martínez-Palou

Authors
  1. Aydeé Fuentes
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  2. Rafael Martínez-Palou
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  3. Hugo A. Jiménez-Vázquez
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  4. Francisco Delgado
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  5. Alicia Reyes
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  6. Joaquín Tamariz
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Correspondence to Joaquín Tamariz.

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Fuentes, A., Martínez-Palou, R., Jiménez-Vázquez, H. et al. Diels-Alder Reactions of 2-Oxazolidinone Dienes in Polar Solvents Using Catalysis or Non-conventional Energy Sources. Monatshefte für Chemie 136, 177–192 (2005). https://doi.org/10.1007/s00706-004-0244-0

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  • DOI: https://doi.org/10.1007/s00706-004-0244-0

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