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Authors
Abstract(s)
The preparation of medicinally relevant small molecules from biomass is a field of interest due to: 1) structural diversity obtained from biomass modification; 2) being potentially more sustainable and environmentally friendly approach, and; 3) more readily available starting materials most likely lead to lower cost of final product.
Biomass furanic platforms, including furfural, have attracted special attention from the scientific community. The transformation of furfural to trans-4,5-diamino-cyclopent-2-enones (DCP) has been extensively studied by several research groups, and different methodologies are now available to obtain these compounds. Being a class of molecules with medicinal interest, taking advantage of cyclopentenone rich scaffold is now an eminent strategy to explore other reactivities and obtain novel bioactive molecules.
The transformation of furfural to DCP continues to be a current topic of research, and in this thesis, we studied the scalability of the process by developing a continuous flow methodology for easier scale up/out taking into consideration sustainability metrics. Moreover, the challenging preparation of some DCP derivatives bearing electron-poor anilines led us to develop a high-pressure methodology, which ended up to improve DCP yields. Our interest in producing bioactive scaffolds under sustainable conditions prompted us to explore the reactivity of DCP based on the valorisation of furfural. In this sense, we developed a continuous flow hydrogenation of DCP using H-Cube® Mini Plus apparatus with high selectivity towards unprecedent 2,3-diaminocyclopentanones and α-enaminones, including an ATP sensitive potassium channel agonist. The sustainability of the method was also accessed by green metrics. The α-enaminone core reactivity was further studied through photochemical transformations and Diels-Alder reaction using α-enaminone as diene.
A series of photochemical reactions were investigated. The carboxylation of in-house prepared aminals and thioaminals was attempted. Thioaminals were prepared in this thesis. The photodecarbonylation of ketones, including 2,3-diaminocyclopentanones, was studied using environmentally friendly ionic liquids, PEG and deep eutectic systems.
Description
Keywords
Sustentabilidade Biomassa Ciclopentenonas α-Enaminonas Química de Fluxo Contínuo Sustainability Biomass Cyclopentenones α-Enaminones , Continuous Flow Chemistry