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Proceeding Paper

Pyrrolidinodiones in Enol-Ugi, Enol-Passerini, and Anomalous Enol-Passerini Condensations †

Departamento de Química Orgánica e Inorgánica, Facultad de Veterinaria, Universidad de Extremadura. Avda. Universidad, s/n, 10003 Cáceres, Spain
*
Author to whom correspondence should be addressed.
Presented at the 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November– 15 December 2018; Available Online: https://sciforum.net/conference/ecsoc-22.
Proceedings 2019, 9(1), 6; https://doi.org/10.3390/ecsoc-22-05864
Published: 19 November 2018

Abstract

In continuation of our recent research on the development of novel multicomponent reactions with isocyanides, we have used, for the first time, enols as the acid components in Ugi- and Passerini-type reactions. Thus, electron-poor pyrrolidinodiones react with aldehydes, amines, and isocyanides to give the enaminic four-component adducts. Conversely, in the absence of the amine component, careful control of the reaction conditions allows the involvement of one or two molecules of isocyanide to afford, selectively, either Passerini-type or pseudo-enol-Ugi-type products. These unprecedented condensations of isocyanides, aldehydes, amines, and 4-substituted pyrrolidine-2,3-diones constitute an excellent strategy for the preparation of new biologically relevant pyrrolidinones having peptidic or pseudo-peptidic groups on carbon 3.
Keywords: multicomponent reactions; isocyanides; enamines; heterocycles. multicomponent reactions; isocyanides; enamines; heterocycles.

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MDPI and ACS Style

Neo, A.G.; Marcos, C.F. Pyrrolidinodiones in Enol-Ugi, Enol-Passerini, and Anomalous Enol-Passerini Condensations. Proceedings 2019, 9, 6. https://doi.org/10.3390/ecsoc-22-05864

AMA Style

Neo AG, Marcos CF. Pyrrolidinodiones in Enol-Ugi, Enol-Passerini, and Anomalous Enol-Passerini Condensations. Proceedings. 2019; 9(1):6. https://doi.org/10.3390/ecsoc-22-05864

Chicago/Turabian Style

Neo, Ana G., and Carlos F. Marcos. 2019. "Pyrrolidinodiones in Enol-Ugi, Enol-Passerini, and Anomalous Enol-Passerini Condensations" Proceedings 9, no. 1: 6. https://doi.org/10.3390/ecsoc-22-05864

APA Style

Neo, A. G., & Marcos, C. F. (2019). Pyrrolidinodiones in Enol-Ugi, Enol-Passerini, and Anomalous Enol-Passerini Condensations. Proceedings, 9(1), 6. https://doi.org/10.3390/ecsoc-22-05864

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