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Synthesis of Diels–Alder adducts of N-arylmaleimides by a multicomponent reaction between maleic anhydride, dienes, and anilines

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Abstract

We have carried out the synthesis and characterization of some hexahydroisoindolyl benzoic acids and their corresponding ethyl esters by a multicomponent reaction (MCR) between aminobenzoic acids or aminobenzoates, maleic anhydride, and isoprene in the absence of catalysts. According to additional experiments, the MCR takes place by sequential formation of N-arylmaleamic acids from the aminobenzoic acids or aminobenzoates and maleic anhydride, Diels–Alder adducts of the acids and isoprene, and finally the imides. The 1H NMR data (coupling constants) of the adducts suggested that the preferred conformation of the corresponding cyclohexene rings is a syn-boat, a fact supported by a density functional theory (DFT) conformational analysis and DFT calculations of the spin–spin coupling constants of the corresponding conformers. Our MCR synthetic methodology was tested successfully in the synthesis of other adducts, for which cyclopentadiene and other anilines were employed.

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Acknowledgements

We thank the Secretaría de Investigación y Posgrado of the Instituto Politécnico Nacional for financial support (Grants: DQZ, 20110101; HAJV, 20100506; JTF, 20100220). DQZ and HAJV are fellows of the COFAA and EDI programs of the IPN. JAGS thanks the Consejo Nacional de Ciencia y Tecnología for the award of a scholarship. We thank Francisco Ayala M.Sc. for the HRMS measurements and Profs. G. Zepeda and J. Tamariz for helpful comments.

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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 s/n, 11340, Mexico, DF, Mexico

    J. Alberto Guevara-Salazar & Hugo A. Jiménez-Vázquez

  2. Laboratorio de Química Orgánica, Centro de Investigación en Ciencia Aplicada y Tecnología Avanzada, Instituto Politécnico Nacional, Calzada Legaria No. 694, 11500, Mexico, DF, Mexico

    Delia Quintana-Zavala

  3. Departamento de Bioquímica, Escuela Superior de Medicina, Instituto Politécnico Nacional, Salvador Díaz Mirón y Plan de San Luis s/n, 11340, Mexico, DF, Mexico

    J. Alberto Guevara-Salazar & José Trujillo-Ferrara

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  1. J. Alberto Guevara-Salazar
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  2. Delia Quintana-Zavala
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  3. Hugo A. Jiménez-Vázquez
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  4. José Trujillo-Ferrara
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Correspondence to José Trujillo-Ferrara.

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Guevara-Salazar, J.A., Quintana-Zavala, D., Jiménez-Vázquez, H.A. et al. Synthesis of Diels–Alder adducts of N-arylmaleimides by a multicomponent reaction between maleic anhydride, dienes, and anilines. Monatsh Chem 142, 827–836 (2011). https://doi.org/10.1007/s00706-011-0515-5

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