Publicação
Synthesis of potentially bioactive Diels-Alder 5-HydroxymethylFurfural adducts
| Resumo: | In the past years, we have come to experience some negative effects of long term world reliance on fossil derived production. The effects on the environment are extensive and observable and, on top of this, chaotic oil market prices have been causing great concern. In the current context, pressure to develop new methods of production derived from renewable sources has extended to all areas of big industry. Chemical Industry is no exception. The majority of carbon based starting molecules are still obtained from fossil feedstock, but now we have been experiencing the increase of new ways for production for these starting materials, leading to a greener chemistry. Here is where 5-hidroxymethylfurfural (5-HMF) comes in to picture. This molecule has been known for some time, but only recently was achieved a reliable, efficient method for production that allows us to consider 5-HMF as a promising starting molecule in synthesis. 5-HMF comprises a furan ring, a structure that has been studied as a substrate for a type of synthetic useful reaction: the inverse electron demand Diels-Alder (IEDDA) reaction. In order to explore the reactivity of 5-HMF type structures in IEDDA, we devised a small compound family composed of several HMF derivatives, acting as dienes, and then tested the formation of DA adducts using 2,3-dihydrofuran (DHF) as dienophile. We optimized some of the reactions leading to the small family of substrates, screening parameters such as solvent used and reaction time. Although the isolation of most of the final adducts was not achieved, the reactivity was observed and can be improved in order to be applied to biological systems, with possible applications in areas such as click chemistry. |
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| Autores principais: | Gonçalves, João Miguel de Jesus |
| Assunto: | HMF 5-hydroxymethylfurfural Inverse-electron demanding Diels-Alder reaction HMF derivatives Mestrado Integrado - 2017 |
| Ano: | 2017 |
| País: | Portugal |
| Tipo de documento: | dissertação de mestrado |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade de Lisboa |
| Idioma: | inglês |
| Origem: | Repositório da Universidade de Lisboa |
| Resumo: | In the past years, we have come to experience some negative effects of long term world reliance on fossil derived production. The effects on the environment are extensive and observable and, on top of this, chaotic oil market prices have been causing great concern. In the current context, pressure to develop new methods of production derived from renewable sources has extended to all areas of big industry. Chemical Industry is no exception. The majority of carbon based starting molecules are still obtained from fossil feedstock, but now we have been experiencing the increase of new ways for production for these starting materials, leading to a greener chemistry. Here is where 5-hidroxymethylfurfural (5-HMF) comes in to picture. This molecule has been known for some time, but only recently was achieved a reliable, efficient method for production that allows us to consider 5-HMF as a promising starting molecule in synthesis. 5-HMF comprises a furan ring, a structure that has been studied as a substrate for a type of synthetic useful reaction: the inverse electron demand Diels-Alder (IEDDA) reaction. In order to explore the reactivity of 5-HMF type structures in IEDDA, we devised a small compound family composed of several HMF derivatives, acting as dienes, and then tested the formation of DA adducts using 2,3-dihydrofuran (DHF) as dienophile. We optimized some of the reactions leading to the small family of substrates, screening parameters such as solvent used and reaction time. Although the isolation of most of the final adducts was not achieved, the reactivity was observed and can be improved in order to be applied to biological systems, with possible applications in areas such as click chemistry. |
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