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Acid-catalysed hydroamination for targeted synthesis

Xue, Zhijuan 2016. Acid-catalysed hydroamination for targeted synthesis. MPhil Thesis, Cardiff University.
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Nitrogen-containing spiro-cyclic compounds mainly exist in naturally occurring compounds and pharmaceutical products. Spiro-cyclic frameworks are characterized by a unique special arrangement of their rings. The main challenge for the preparation of the spirocyclic motif is regio-controlled and stereo-controlled generation of a quaternary carbon center. Known methods for spiro-cyclic compounds include alkylation and cyclisation, condensation reactions, rearrangement reactions, metal-catalysed reactions, and ring closing metathesis are reviewed. Brønsted acid-catalysed hydroamination in the synthesis of pyrrolidines and spiro-pyrrolidines has been investigated in the Knight group for a long time. This methodology is of great convenience and can be efficient for targeted cyclic and spiro-cyclic compounds synthesis. A tris-piperidine structure, a potential lead compound for an ant-cancer drug, originates from a computer study carried out at Cancer Research UK. This small molecule was found which could bind to known sites present in various cancer cells. This thesis describes the application of triflic acid-catalysed cyclisation in the synthesis of the targeted spiro-piperidines and tris-piperidines. In section one, an introduction of anticancer drugs and anticancer drugs discovery is given, together with the background of the current project. Section two summarizes known methods for spiro-cyclic compounds synthesis, and applications of triflic acid-catalysed cyclisation in the Knight group are reviewed in section three. Section four describes different synthetic routes towards the construction of amino-alkenes and cyclisation into spiro-cyclic compound via acid-catalysed hydroamination methodology. Attempts to synthesize 1,3-disubstituted-dithianes for the preparation of spiro-piperidine and tris-piperidine are also discussed. Chapter five contains the experimental data.

Item Type: Thesis (MPhil)
Status: Unpublished
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Date of First Compliant Deposit: 30 May 2017
Last Modified: 04 Jun 2017 09:51

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