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Keywords = piperazinone enaminoesters

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18 pages, 7770 KiB  
Article
Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters
by Rebecca Hermans, Max Van Hoof, Luc Van Meervelt and Wim Dehaen
Organics 2023, 4(2), 146-163; https://doi.org/10.3390/org4020012 - 7 Apr 2023
Cited by 1 | Viewed by 2690
Abstract
The Nenitzescu reaction is a condensation reaction between an enamine and a quinone, which can give rise to a wide variety of reaction products depending on the nature of the starting material and the reaction conditions. The most commonly observed products are 5-hydroxyindoles [...] Read more.
The Nenitzescu reaction is a condensation reaction between an enamine and a quinone, which can give rise to a wide variety of reaction products depending on the nature of the starting material and the reaction conditions. The most commonly observed products are 5-hydroxyindoles and 5-hydroxybenzofurans. Both classes are of interest since they are known to possess a variety of promising bioactivities. Despite the high chemodivergency for this reaction, it remains an interesting synthetic strategy thanks to the mild reaction conditions, easily accessible starting materials and simple reaction procedures. For these reasons, our research group investigated the Nenitzescu reaction of piperazinone enaminoesters, resulting in the unexpected formation of rearranged 2-imidazolidinone benzofurans. In this work, we aimed to develop reaction conditions that favor the formation of 5-hydroxyindoles via an extensive, multivariate optimization study. This led to valuable insights into the parameters that influence regio- and chemoselectivity. Furthermore, two novel products were obtained, a pyrrolo[2,3-f]indole and a benzofuranone, both of which are rarely reported in the literature. Full article
(This article belongs to the Special Issue Chemistry of Heterocycles)
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