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On the Reactivity of N-Substituted Imidates Towards 1,4-Bisnucleophiles: An Experimental and Theoretical Study

Chemistry Africa volume 5, pages 1265–1273 (2022)Cite this article

Abstract

This paper sets out to describe the reaction of N-acyl and N-ethoxycarbonyl imidates with 1,4-bisnucleophiles. The reaction selectively led to 5-membered heterocycles in good yields instead of expected 7-membered ring systems. Using mild reaction conditions, we synthesized 2-imidazoline, benzimidazolines, 2-oxazoline, 2-thiazoline and 2-dithiolane derivatives. Experimental results are supported by theoretical DFT calculations. Our approach has been further extended to 1,5 bis amines towards tetrahydropyrimidine scaffolds.

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Acknowledgements

Authors are grateful to the Tunisian Ministry of Higher Education and Scientific Research, the University of Tunis El Manar, the CNRS, and to the Universities of Paris-Saclay and Versailles Saint Quentin.

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Authors and Affiliations

  1. Laboratoire de synthèse organique et hétérocyclique sélective-Evaluation d’activité biologique LR17ES01, Université de Tunis El Manar, Faculté des Sciences de Tunis, Campus universitaire, 2092, Tunis, Tunisia

    Sarra Ouni, Abderrahmen Abdelli & Mohamed Lotfi Efrit

  2. Université Paris-Saclay, UVSQ, CNRS, Institut Lavoisier de Versailles, 78035, Versailles, France

    Sarra Ouni, Anne Gaucher & Damien Prim

  3. Laboratoire de caractérisations, applications et modélisation des matériaux LR18ES08, Département de chimie, Faculté des sciences, Université de Tunis El Manar, 2092, Tunis, Tunisia

    Youssef Arfaoui

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  1. Sarra Ouni
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  2. Abderrahmen Abdelli
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  3. Anne Gaucher
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  4. Youssef Arfaoui
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  5. Damien Prim
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  6. Mohamed Lotfi Efrit
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Correspondence to Damien Prim or Mohamed Lotfi Efrit.

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Ouni, S., Abdelli, A., Gaucher, A. et al. On the Reactivity of N-Substituted Imidates Towards 1,4-Bisnucleophiles: An Experimental and Theoretical Study. Chemistry Africa 5, 1265–1273 (2022). https://doi.org/10.1007/s42250-022-00452-y

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