Next Article in Journal
Electrochemical Performance of Nitrogen-Doped TiO2 Nanotubes as Electrode Material for Supercapacitor and Li-Ion Battery
Previous Article in Journal / Special Issue
Design, Synthesis, and Biological Evaluation of Novel N-Acylhydrazone Bond Linked Heterobivalent β-Carbolines as Potential Anticancer Agents
Open AccessCommunication

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
Authors to whom correspondence should be addressed.
Academic Editor: Gianfranco Favi
Molecules 2019, 24(16), 2951;
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)
PDF [2400 KB, uploaded 22 August 2019]


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. View Full-Text
Keywords: γ-lactam; pyrrolidones; multicomponent reactions; organocatalysis γ-lactam; pyrrolidones; multicomponent reactions; organocatalysis

Graphical abstract

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).

Supplementary material


Share & Cite This Article

MDPI and ACS Style

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

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top