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Synthesis of Nitrogen Heterocycles by Hypervalent Iodine Mediated Cyclization

Ibrahim, Mohamed Raif; (2022) Synthesis of Nitrogen Heterocycles by Hypervalent Iodine Mediated Cyclization. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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Abstract

This thesis discusses the synthesis of 3-arylpyrrolidin-2-ones and the use of hypervalent iodine reagents in organic synthesis. With that being the case, the first chapter provides a brief introduction to nitrogen heterocycles and discusses methods for the synthesis of 3-arylpyrrolidin-2-ones. The second chapter provides an introduction to the bonding and reactivity of hypervalent iodine reagents. The third chapter explores the prior applications of hypervalent iodine reagent in organic synthesis with a focus on areas relevant to this work. This includes the use of hypervalent iodine reagents in the functionalization of alkynes, in nitrogen heterocycle synthesis and in various migratory reactions. The fourth chapter discusses the results of an investigation into the synthesis of pyrrolidinones. A novel synthesis of 3-arylpyrrolidin-2-ones by a hypervalent iodine induced cyclization-rearrangement cascade reaction is reported. Starting from N-(4-arylbut-3-yn-1-yl)tosylamides, the initial cyclization gives an intermediary β-arylvinyl(phenyl)iodonium salt which has been isolated and characterized by NMR spectroscopy. Hydration of this intermediate leads to the generation of 3-arylpyrrolidin-2-ones by a 1,2-aryl shift with expulsion of iodobenzene. The fifth chapter summarizes the results and suggests some avenues for future research. The final chapter provides the experimental details and characterization data for compounds isolated during the course of this work.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Synthesis of Nitrogen Heterocycles by Hypervalent Iodine Mediated Cyclization
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Copyright © The Author 2021. Original content in this thesis is licensed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) Licence (https://creativecommons.org/licenses/by-nc/4.0/). Any third-party copyright material present remains the property of its respective owner(s) and is licensed under its existing terms. Access may initially be restricted at the author’s request.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10161927
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