Issue 5, 2022
From the journal:

New Journal of Chemistry

2-Imidazolidinone benzofurans as unexpected outcome of the Lewis acid mediated Nenitzescu reaction†

Tomas Horsten, ORCID logo a   Temitayo Omowumi Alegbejo Price, ORCID logo b   Luc Van Meervelt, ORCID logo c   Flavio da Silva Emery ORCID logo b  and  Wim Dehaen ORCID logo *a  

* Corresponding authors

a Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven 3001, Belgium
E-mail: wim.dehaen@kuleuven.be

b Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences at Ribeirao Preto of the University of Sao Paulo, Ribeirao Preto, SP, Brazil

c Biochemistry, Molecular and Structural Biology Section, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven 3001, Belgium

Abstract

The Lewis acid mediated Nenitzescu reaction with piperazinone enaminoesters surprisingly afforded rearranged 2-imidazolidinone 5-hydroxybenzofurans. The reaction was optimised and a scope study was performed. A one-pot two-step procedure was realised starting directly from 1,2-diaminoethane, diethyl acetylene dicarboxylate and 1,4-benzoquinone. A plausible reaction mechanism is proposed.

Graphical abstract: 2-Imidazolidinone benzofurans as unexpected outcome of the Lewis acid mediated Nenitzescu reaction

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Article information

DOI
https://doi.org/10.1039/D1NJ04965H
Article type
Communication
Submitted
18 Oct 2021
Accepted
11 Jan 2022
First published
11 Jan 2022

New J. Chem., 2022,46, 2028-2032

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2-Imidazolidinone benzofurans as unexpected outcome of the Lewis acid mediated Nenitzescu reaction

T. Horsten, T. O. Alegbejo Price, L. Van Meervelt, F. D. S. Emery and W. Dehaen, New J. Chem., 2022, 46, 2028 DOI: 10.1039/D1NJ04965H

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