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Towards Understanding the Synthesis and Reactivity of Alkynyl Sulfonamides

Luo, Yi; (2021) Towards Understanding the Synthesis and Reactivity of Alkynyl Sulfonamides. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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Abstract

This thesis discusses the importance of the sulfonamide motif both in medicinal chemistry and as a synthetic tool. Particular focus is given to the alkynyl sulfonamide, a useful alkyne that first attracted the attention of this research group when it was shown to possess potential in the synthesis of ynol ethers. As the reactivity of alkynyl sulfonamides is relatively unexplored, there is interest in expanding the knowledge base of reactions that the alkynyl sulfonamide can undergo with medical applications in mind. With that being the case, this project has explored routes towards a one pot synthesis of alkynyl sulfonamides, which, whilst successful, proved to be largely unscalable. However, this led to the development of other analogues that demonstrated similar reactivity to alkynyl sulfonamides in addition-elimination reactions to form ynol ethers. Secondly, a range of novel “drug-like” 2,3-dihydroisoxazoles was developed by reacting alkynyl sulfonamides with nitrones in a 1,3-dipolar cycloaddition reaction. The reactions are rapid and lead to the formation of one regioisomer in good yields, with several of these compounds exhibiting promising biological activity in vitro. Novel 4,5-dihydroisoxazoles were also synthesized by reacting alkenyl sulfonamides with nitrile oxides in a 1,3-dipolar cycloaddition to form one regioisomer in good yields. Lastly, a small range of novel isoxazoles was synthesized through two routes: a 1,3-dipolar cycloaddition between alkynyl sulfonamides and nitrile oxides; and a 1,3-dipolar cycloaddition between alkenyl sulfonamides and nitrile oxides, followed by elimination of the sulfonamide.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Towards Understanding the Synthesis and Reactivity of Alkynyl Sulfonamides
Event: UCL (University College London)
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 4.0 International (CC BY 4.0) Licence (https://creativecommons.org/licenses/by/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/10131773
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