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A Brønsted Acid-Catalyzed Multicomponent Reaction for the Synthesis of Highly Functionalized γ-Lactam Derivatives

Departamento de Química Orgánica I, Centro de Investigación y Estudios Avanzados “Lucio Lascaray”- Facultad de Farmacia, University of the Basque Country, UPV/EHU Paseo de la Universidad 7, 01006 Vitoria-Gasteiz, Spain
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Academic Editor: Gianfranco Favi
Molecules 2019, 24(16), 2951; https://doi.org/10.3390/molecules24162951
Received: 24 July 2019 / Revised: 6 August 2019 / Accepted: 11 August 2019 / Published: 14 August 2019
(This article belongs to the Special Issue Modern Strategies for Heterocycle Synthesis)
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Abstract

Brønsted acids catalyze a multicomponent reaction of benzaldehyde with amines and diethyl acetylenedicarboxylate to afford highly functionalized γ-lactam derivatives. The reaction consists of a Mannich reaction of an enamine to an imine, both generated in situ, promoted by a phosphoric acid catalyst and a subsequent intramolecular cyclization. The hydrolysis of the cyclic enamine substrate can provide enol derivatives and, moreover, a second attack of the amine on the carboxylate can afford amide derivatives. An optimization of the reaction conditions is presented in order to obtain selectively cyclic enamines that can afford the enol species after selective hydrolysis.
Keywords: γ-lactam; pyrrolidones; multicomponent reactions; organocatalysis γ-lactam; pyrrolidones; multicomponent reactions; organocatalysis
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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 (CC BY 4.0).

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Corte, X.; Marigorta, E.M.; Palacios, F.; Vicario, J. A Brønsted Acid-Catalyzed Multicomponent Reaction for the Synthesis of Highly Functionalized γ-Lactam Derivatives. Molecules 2019, 24, 2951.

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