Towards biologically active heterocycles from renewable aromatic starting materials

This thesis describes work undertaken over the past three years as part of the EPSRC Centre for Doctoral Training in Sustainable Chemistry. Our focus was on developing methods to generate the same important molecules in new, and better ways as judged by green & sustainability criteria. Overall,...

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Main Author: Anderson, Edward
Format: Thesis (University of Nottingham only)
Language:English
Published: 2019
Subjects:
Online Access:https://eprints.nottingham.ac.uk/56834/
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author Anderson, Edward
author_facet Anderson, Edward
author_sort Anderson, Edward
building Nottingham Research Data Repository
collection Online Access
description This thesis describes work undertaken over the past three years as part of the EPSRC Centre for Doctoral Training in Sustainable Chemistry. Our focus was on developing methods to generate the same important molecules in new, and better ways as judged by green & sustainability criteria. Overall, we have concentrated our efforts on the synthesis of heterocyclic molecules within the context of biologically active molecules. This has ranged from the synthesis of aromatic heterocycles in the form of naphthyridines, to the dearomatisation of aromatic molecules to generate spirocyclic, unsaturated amines. We have successfully developed a greener, as judged by reaction metrics, method for the synthesis of 1,8-naphthyridines. In addition, we have produced a method for the synthesis of a previously unreported heterocycle that can likely find use as an electrophilic building block in synthetic chemistry. Furthermore, we have shown that one can oxidatively dearomatise phenols in the presence of tethered tertiary tert-butyl carbamates to afford spirocyclic tertiary amine products, using iodine(III) reagents as an oxidant.
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spelling nottingham-568342025-02-28T14:33:02Z https://eprints.nottingham.ac.uk/56834/ Towards biologically active heterocycles from renewable aromatic starting materials Anderson, Edward This thesis describes work undertaken over the past three years as part of the EPSRC Centre for Doctoral Training in Sustainable Chemistry. Our focus was on developing methods to generate the same important molecules in new, and better ways as judged by green & sustainability criteria. Overall, we have concentrated our efforts on the synthesis of heterocyclic molecules within the context of biologically active molecules. This has ranged from the synthesis of aromatic heterocycles in the form of naphthyridines, to the dearomatisation of aromatic molecules to generate spirocyclic, unsaturated amines. We have successfully developed a greener, as judged by reaction metrics, method for the synthesis of 1,8-naphthyridines. In addition, we have produced a method for the synthesis of a previously unreported heterocycle that can likely find use as an electrophilic building block in synthetic chemistry. Furthermore, we have shown that one can oxidatively dearomatise phenols in the presence of tethered tertiary tert-butyl carbamates to afford spirocyclic tertiary amine products, using iodine(III) reagents as an oxidant. 2019-07-17 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/56834/1/PhD%20Thesis%20-%20Edward%20Christopher%20Anderson%204230938%20with%20corrections.pdf Anderson, Edward (2019) Towards biologically active heterocycles from renewable aromatic starting materials. PhD thesis, University of Nottingham. Heterocyclic compounds; Naphthyridines Synthesis; Aromatic compounds
spellingShingle Heterocyclic compounds; Naphthyridines
Synthesis; Aromatic compounds
Anderson, Edward
Towards biologically active heterocycles from renewable aromatic starting materials
title Towards biologically active heterocycles from renewable aromatic starting materials
title_full Towards biologically active heterocycles from renewable aromatic starting materials
title_fullStr Towards biologically active heterocycles from renewable aromatic starting materials
title_full_unstemmed Towards biologically active heterocycles from renewable aromatic starting materials
title_short Towards biologically active heterocycles from renewable aromatic starting materials
title_sort towards biologically active heterocycles from renewable aromatic starting materials
topic Heterocyclic compounds; Naphthyridines
Synthesis; Aromatic compounds
url https://eprints.nottingham.ac.uk/56834/