Studies in the synthesis and impurity profiling of pharmacologically active benzodifurans

Substituted 2,3-dihydrobenzofuran derivatives as well as their benzofuran and benzodifuranyl analogues are versatile heterocycles that are increasing in prominence as key building blocks in organic chemistry. In particular, benzodifuran-containing structures are gaining significant interest in medicinal chemistry as pharmacophores and in industrial chemistry as scaffolds for organic electroluminescent devices, organic field-effect transistors, solar cell sensitizers and semiconducting polymers. The synthesis of pharmacologically active benzodifurans are complex multi-step processes and each individual step has the potential for considerable side-product/impurity formation. This project focused on synthetic strategies to benzofuran and benzodifuran derivatives in addition to their hydrogenated and substituted analogues. The chosen synthetic routes to target molecules further focused on the propensity of synthetic steps to produce impurities, modifiable variables to modulate impurity formation and the impurity profile of each synthetic route explored. Organic process impurities identified were isolated and fully characterised where possible, in addition to intended products.

Grantor dc:publisher

University College Cork

Year dc:date.issued

2022

Author dc:creator

• O'Connor, Richard Eric

Advisor dc:contributor.advisor

• Keating, J J

• Pharmacologically active benzodifurans
• Impurity profiling
• Ketone precurso
• Novel Isomers
• Benzodifuran scaffolds
• Anti-cancer
• Regio-specific halogenation
• Benzodifuran ring closure

Statement dc:rights

• © 2023, Richard Eric O'Connor.

Licence dc:rights.uri

• https://creativecommons.org/licenses/by-nc-nd/4.0/

Language dc:language.iso

en

Handle dc:identifier.uri

https://hdl.handle.net/10468/15532

OAI identifier oai:identifier

oai:cora.ucc.ie:10468/15532