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Organics, Volume 4, Issue 2

2023 June - 14 articles

Cover Story: The Nenitzescu reaction is a condensation reaction between an enamine and a quinone, most commonly resulting in 5-hydroxyindoles and 5-hydroxybenzofurans with promising bioactivities. Despite the high chemodivergency for this reaction, it remains of interest due to the mild reaction conditions, easily accessible starting materials and simple reaction procedures. Earlier investigation of the Nenitzescu reaction of piperazinone enaminoesters led to rearranged 2-imidazolidinone benzofurans. In this work, we aimed to develop reaction conditions that favor the formation of 5-hydroxyindoles via an extensive, multi-variate optimization study. This led to valuable insights into the parameters that influence regio- and chemoselectivity. Furthermore, two novel products were obtained, pyrrolo[2,3-f]indole and 2-benzofuranone. View this paper
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Organics - ISSN 2673-401X
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