Gold(III) Chloride-Mediated Transformation of Furfural to the <i>trans</i>-<i>N</i>,<i>N</i>-4,5-Diaminocyclopent-2-enones in the Presence of Anilines

We investigated the efficient approach of a series of <i>trans</i>-<i>N</i>,<i>N</i>-4,5-substituted-diaminocyclopent-2-enones (<i>trans</i>-DACPs) from furfural and anilines mediated by Gold(III) chloride (HAuCl<sub>4</sub>). The present p...

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Bibliographic Details
Main Authors: Marina A. Tzani, Ioannis N. Lykakis
Format: Article
Language:English
Published: MDPI AG 2023-02-01
Series:Chemistry
Subjects:
Online Access:https://www.mdpi.com/2624-8549/5/1/29
Description
Summary:We investigated the efficient approach of a series of <i>trans</i>-<i>N</i>,<i>N</i>-4,5-substituted-diaminocyclopent-2-enones (<i>trans</i>-DACPs) from furfural and anilines mediated by Gold(III) chloride (HAuCl<sub>4</sub>). The present protocol required a low amount of the catalysts, 1.5 mol%, open air conditions, the absence of any additives, and short reaction times. The desired <i>trans</i>-DACPs were isolated in good to high yields. The protocol was also applied to secondary amines, leading to the corresponding 4,5-diamino-cyclopent-2-enones in good yields. To the best of our knowledge, this is the first gold-mediated paradigm as an efficient catalyst for the formation of the cyclopentenones core-bearing C-N bonds under mild reaction conditions.
ISSN:2624-8549