Trifluoroethanol Promoted Castagnoli–Cushman Cycloadditions of Imines with Homophthalic Anhydride

Lactams are essential compounds in medicinal chemistry and key intermediates in the synthesis of natural products. The Castagnoli–Cushman reaction (CCR) of homophthalic anhydride with imines is an exciting method for accessing cyclic densely substituted lactam products. Most CCRs need to be catalyze...

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Detalles Bibliográficos
Autores principales: Bayles, Thibault, Guillou, Catherine
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8839191/
https://www.ncbi.nlm.nih.gov/pubmed/35164109
http://dx.doi.org/10.3390/molecules27030844
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author Bayles, Thibault
Guillou, Catherine
author_facet Bayles, Thibault
Guillou, Catherine
author_sort Bayles, Thibault
collection PubMed
description Lactams are essential compounds in medicinal chemistry and key intermediates in the synthesis of natural products. The Castagnoli–Cushman reaction (CCR) of homophthalic anhydride with imines is an exciting method for accessing cyclic densely substituted lactam products. Most CCRs need to be catalyzed or heated. Herein, we report a new, efficient, metal and catalyst-free CCR for the synthesis of poly-substituted 3,4-lactams utilizing the unique properties of trifluoroethanol (TFE). This procedure provides high-speed and smooth access to a broad range of densely substituted 3,4-lactams in good yields and a 100% atom-economical fashion.
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spelling pubmed-88391912022-02-13 Trifluoroethanol Promoted Castagnoli–Cushman Cycloadditions of Imines with Homophthalic Anhydride Bayles, Thibault Guillou, Catherine Molecules Communication Lactams are essential compounds in medicinal chemistry and key intermediates in the synthesis of natural products. The Castagnoli–Cushman reaction (CCR) of homophthalic anhydride with imines is an exciting method for accessing cyclic densely substituted lactam products. Most CCRs need to be catalyzed or heated. Herein, we report a new, efficient, metal and catalyst-free CCR for the synthesis of poly-substituted 3,4-lactams utilizing the unique properties of trifluoroethanol (TFE). This procedure provides high-speed and smooth access to a broad range of densely substituted 3,4-lactams in good yields and a 100% atom-economical fashion. MDPI 2022-01-27 /pmc/articles/PMC8839191/ /pubmed/35164109 http://dx.doi.org/10.3390/molecules27030844 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Bayles, Thibault
Guillou, Catherine
Trifluoroethanol Promoted Castagnoli–Cushman Cycloadditions of Imines with Homophthalic Anhydride
title Trifluoroethanol Promoted Castagnoli–Cushman Cycloadditions of Imines with Homophthalic Anhydride
title_full Trifluoroethanol Promoted Castagnoli–Cushman Cycloadditions of Imines with Homophthalic Anhydride
title_fullStr Trifluoroethanol Promoted Castagnoli–Cushman Cycloadditions of Imines with Homophthalic Anhydride
title_full_unstemmed Trifluoroethanol Promoted Castagnoli–Cushman Cycloadditions of Imines with Homophthalic Anhydride
title_short Trifluoroethanol Promoted Castagnoli–Cushman Cycloadditions of Imines with Homophthalic Anhydride
title_sort trifluoroethanol promoted castagnoli–cushman cycloadditions of imines with homophthalic anhydride
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8839191/
https://www.ncbi.nlm.nih.gov/pubmed/35164109
http://dx.doi.org/10.3390/molecules27030844
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