The aim of this project is to develop a series of conceptually new reactions to make nitrogen-containing medium/macrocyclic rings, directly from linear precursors via novel cascade reactions. Direct cyclisation reactions to make larger rings molecules (e.g. preparing a 10-membered ring from a linear precursor) are usually slow/difficult processes. We propose that theses larger ring frameworks may be more effectively synthesised from alternative linear precursors in which nucleophiles built into the middle of the linear starting material is used to mediate a cyclisation/ring expansion reaction cascade sequence. Thus, if all discrete cyclisation reactions proceed via comparatively easy, low-energy ‘normal’-sized cyclic transition states, it is reasonable to expect that this will enable a more favourable reaction course to be followed.
We propose to do this by designing nitrogen-containing linear molecules capable of undergo ‘Nucleophile Induced Cyclisation/Expansion’ (NICE) cascade reactions. Our group’s previous work has shown the value of ring expansion approaches to construct complex aza-macroycles and medium rings (see references 1-4) but this project will reply on the development of completely new chemistry, based on our recent published proof of concept study (reference 5) and should enable complex nitrogen-containing medium/macrocyclic rings to be prepared in new, efficient and practical ways. The project will suit candidates interested in the development of new synthetic methodology and target synthesis. Candidates who enjoy retrosynthetic analysis and applying their organic synthesis knowledge with creativity and imagination are especially encouraged to apply. Opportunities to explore and study the biological/medicinal properties of the molecules will also be explored; indeed, the balance of how much focus is placed on synthesis and potential applications can be tailored to suit the interests of PhD candidate.
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