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A Maitland Japp Inspired Synthesis of 2-Spiropiperidines

Griggs, Samuel (2018) A Maitland Japp Inspired Synthesis of 2-Spiropiperidines. PhD thesis, University of York.

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Abstract

With a growing desire to explore three-dimensional chemical space, methods for the synthesis of spirocyclic compounds, more specifically aza-spirocycles, are becoming of great interest to medicinal chemists. The synthesis of 3- and 4-spiropiperidines are well documented, however, there is little precedent for the synthesis of 2-spiropiperidines. The research detailed in this thesis describes the efforts towards the synthesis of 2- spiropiperidines via both a stepwise (Scheme i) and a one-pot procedure (Scheme ii), for use in a fragment drug discovery programme. The scopes of the procedures are demonstrated by the synthesis of a diverse range of 2-spiropiperidines. The 2-spiropiperidines were utilised as scaffolds to construct a small library of lead-like compounds that were analysed by LLAMA and principal moments of inertia analysis. The 2-spiropiperidines were consequently found to be three-dimensional. Methods for the construction of other structurally interesting piperidines are also presented, including bridged piperidines, fused piperidines, and 6- spiropiperidines, though the efforts were unsuccessful.

Item Type: Thesis (PhD)
Academic Units: The University of York > Chemistry (York)
Depositing User: Mr Samuel Griggs
Date Deposited: 14 Dec 2018 14:25
Last Modified: 14 Dec 2018 14:25
URI: http://etheses.whiterose.ac.uk/id/eprint/22332

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