A DMPU’s study: characterization and applicability as solvent in organic reactions

Detalhes bibliográficos
Autor(a) principal: Santos, Ricardo Alexandre Luís Silva
Data de Publicação: 2020
Tipo de documento: Dissertação
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10773/30551
Resumo: This work focus on 1,3-dimethyl-1,3-diazinan-2-one (DMPU) as a dipolar aprotic green solvent with applicability in organic synthesis. Its solvatochromic parameters were determined. Afterward, it was tested as a solvent in the Claisen-Smith condensation of 2-hydroxyacetophenone with benzaldehydes, aiming to obtain chalcone derivatives. Furthermore, it was also tested in chalcones cyclodehydrogenation to obtain flavone derivatives. The protocols were optimized to use microwave radiation, and the desired products were obtained in poor to good yields under microwave radiation. The product’s precipitation problem was addressed. A new approach was proposed, in which the organic compound precipitates in dichloromethane. Flavanone was obtained as a side product in chalcones cyclodehydrogenation. All the synthesized compounds were characterized by monodimensional nuclear magnetic resonance (1H and 13C).
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spelling A DMPU’s study: characterization and applicability as solvent in organic reactionsDMPUGreen solventChalconeFlavoneFlavanoneOrganic synthesisSolvatochromic parameterNMR characterizationThis work focus on 1,3-dimethyl-1,3-diazinan-2-one (DMPU) as a dipolar aprotic green solvent with applicability in organic synthesis. Its solvatochromic parameters were determined. Afterward, it was tested as a solvent in the Claisen-Smith condensation of 2-hydroxyacetophenone with benzaldehydes, aiming to obtain chalcone derivatives. Furthermore, it was also tested in chalcones cyclodehydrogenation to obtain flavone derivatives. The protocols were optimized to use microwave radiation, and the desired products were obtained in poor to good yields under microwave radiation. The product’s precipitation problem was addressed. A new approach was proposed, in which the organic compound precipitates in dichloromethane. Flavanone was obtained as a side product in chalcones cyclodehydrogenation. All the synthesized compounds were characterized by monodimensional nuclear magnetic resonance (1H and 13C).Este trabalho focou-se no 1,3-dimetil-1,3-diazinan-2-ona (DMPU) como um solvente verde dipolar aprótico e com aplicabilidade em sínteses orgânicas. Primeiro foram determinados os parâmetros solvatocrómicos do solvente. Posteriormente, ele foi testado como solvente na condensação Claisen-Smith de 2-hidroxiacetofenona com benzaldeídos, para obter derivados de calcona. Além disso, também foi testado na ciclode-hidrogenação de calconas para produzir derivados de flavona. Os protocolos foram otimizados para usar radiação microondas e os produtos foram obtidos com rendimentos baixos a bons, sob radiação micro-ondas. O problema da precipitação dos produtos foi resolvido. A solução proposta consiste na precipitação dos compostos orgânicos em diclorometano. Também foi obtida flavanona como produto secundário da ciclode-hidrogenação das calconas. Todos os compostos sintetizados foram caracterizados por ressonância magnética nuclear (1H e 13C).2021-12-03T00:00:00Z2020-11-27T00:00:00Z2020-11-27info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfhttp://hdl.handle.net/10773/30551engSantos, Ricardo Alexandre Luís Silvainfo:eu-repo/semantics/embargoedAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-02-22T11:59:01Zoai:ria.ua.pt:10773/30551Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:02:36.876031Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv A DMPU’s study: characterization and applicability as solvent in organic reactions
title A DMPU’s study: characterization and applicability as solvent in organic reactions
spellingShingle A DMPU’s study: characterization and applicability as solvent in organic reactions
Santos, Ricardo Alexandre Luís Silva
DMPU
Green solvent
Chalcone
Flavone
Flavanone
Organic synthesis
Solvatochromic parameter
NMR characterization
title_short A DMPU’s study: characterization and applicability as solvent in organic reactions
title_full A DMPU’s study: characterization and applicability as solvent in organic reactions
title_fullStr A DMPU’s study: characterization and applicability as solvent in organic reactions
title_full_unstemmed A DMPU’s study: characterization and applicability as solvent in organic reactions
title_sort A DMPU’s study: characterization and applicability as solvent in organic reactions
author Santos, Ricardo Alexandre Luís Silva
author_facet Santos, Ricardo Alexandre Luís Silva
author_role author
dc.contributor.author.fl_str_mv Santos, Ricardo Alexandre Luís Silva
dc.subject.por.fl_str_mv DMPU
Green solvent
Chalcone
Flavone
Flavanone
Organic synthesis
Solvatochromic parameter
NMR characterization
topic DMPU
Green solvent
Chalcone
Flavone
Flavanone
Organic synthesis
Solvatochromic parameter
NMR characterization
description This work focus on 1,3-dimethyl-1,3-diazinan-2-one (DMPU) as a dipolar aprotic green solvent with applicability in organic synthesis. Its solvatochromic parameters were determined. Afterward, it was tested as a solvent in the Claisen-Smith condensation of 2-hydroxyacetophenone with benzaldehydes, aiming to obtain chalcone derivatives. Furthermore, it was also tested in chalcones cyclodehydrogenation to obtain flavone derivatives. The protocols were optimized to use microwave radiation, and the desired products were obtained in poor to good yields under microwave radiation. The product’s precipitation problem was addressed. A new approach was proposed, in which the organic compound precipitates in dichloromethane. Flavanone was obtained as a side product in chalcones cyclodehydrogenation. All the synthesized compounds were characterized by monodimensional nuclear magnetic resonance (1H and 13C).
publishDate 2020
dc.date.none.fl_str_mv 2020-11-27T00:00:00Z
2020-11-27
2021-12-03T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
format masterThesis
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10773/30551
url http://hdl.handle.net/10773/30551
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/embargoedAccess
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instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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