Reações entre (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas e aminoácidos para produção de heterociclos de 5, 6 e 7 membros
Ano de defesa: | 2022 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
Brasil
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/25863 |
Resumo: | This work present the versatility of 4-alkoxy-5-bromo-1,1,1-trialopent-3-en-2-ones in reactions with amino acids, exploring the four reactive centers of this building block and leading to the formation of heterocycles of 5, 6 and 7 members. Initially, a regioselective protocol was developed, using α-amino acids free of protecting groups, in one-pot reactions to obtain enantiomerically pure morpholin-2-ones. The reaction was selective for the formation of the Z regioisomer in all cases, however when a secondary amino group was used, only the E isomer was observed. The synthesized compounds were obtained in up to 92% yields. In the second step, the protocol previously developed was treated with β-amino acids derived from 4 and 5 substituted 2-aminobenzoic acids affording the corresponding of 7-membered heterocycles, benzoxazepinones, with up to 86% yields. These series of compounds showed solid state fluorescence and studies were carried out on their photophysical properties and their interaction with CT-DNA and BSA. In the third stage of the work, a series of 5-bromo enamino esters were synthesized, wich where used as intermediate for the synthesis of 3 differents heterocycles; in this regard, a séries of reaction parameters were evaluated incluiding, solvent, temperature and base. For instance using inorganic bases it was possible to synthesize furans with up to 85% yield. With primary amines, a selective reaction pathway was obtained for the formation of pyrroles with up to 93% yield, and piperazin-2-ones with 91% yield. The heterocycles developed in this work have structures similar to compounds with biological activity, making it interesting to study their properties. The structures of the compounds were elucidated by 1H, 13C NMR experiments, 2D NMR analyzes as well as X-ray experiments. |
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2022-08-11T13:23:07Z2022-08-11T13:23:07Z2022-05-13http://repositorio.ufsm.br/handle/1/25863This work present the versatility of 4-alkoxy-5-bromo-1,1,1-trialopent-3-en-2-ones in reactions with amino acids, exploring the four reactive centers of this building block and leading to the formation of heterocycles of 5, 6 and 7 members. Initially, a regioselective protocol was developed, using α-amino acids free of protecting groups, in one-pot reactions to obtain enantiomerically pure morpholin-2-ones. The reaction was selective for the formation of the Z regioisomer in all cases, however when a secondary amino group was used, only the E isomer was observed. The synthesized compounds were obtained in up to 92% yields. In the second step, the protocol previously developed was treated with β-amino acids derived from 4 and 5 substituted 2-aminobenzoic acids affording the corresponding of 7-membered heterocycles, benzoxazepinones, with up to 86% yields. These series of compounds showed solid state fluorescence and studies were carried out on their photophysical properties and their interaction with CT-DNA and BSA. In the third stage of the work, a series of 5-bromo enamino esters were synthesized, wich where used as intermediate for the synthesis of 3 differents heterocycles; in this regard, a séries of reaction parameters were evaluated incluiding, solvent, temperature and base. For instance using inorganic bases it was possible to synthesize furans with up to 85% yield. With primary amines, a selective reaction pathway was obtained for the formation of pyrroles with up to 93% yield, and piperazin-2-ones with 91% yield. The heterocycles developed in this work have structures similar to compounds with biological activity, making it interesting to study their properties. The structures of the compounds were elucidated by 1H, 13C NMR experiments, 2D NMR analyzes as well as X-ray experiments.Este trabalho apropria-se da versatilidade das 4-alcoxi-5-bromo-1,1,1-trialopent-3-en-2-onas em reações com aminoácidos, explorando os quatro centros reativos desse bloco construtor e levando a formação de heterociclos de 5, 6 e 7 membros. Na primeira etapa foi desenvolvido um protocolo regiosseletivo, utilizando α-aminoácidos livres de grupos protetores, em reações one-pot para obter morfolin-2-onas enantiomericamente puras. A reação foi seletiva na formação do regioisômero Z em todos os casos, independentemente do α-aminoácido utilizado, no entanto quando um grupo amino secundário foi usado, apenas o isômero E foi observado. Os compostos sintetizados foram obtidos com rendimentos de até 92%. A segunda etapa utilizou o protocolo desenvolvido anteriormente testando frente à β-aminoácidos derivados dos ácidos 2-aminobenzóicos 4 e 5 substituídos levando à formação de heterociclos de 7 membros, benzoxazepinonas, com rendimentos de até 86%. Essa série de compostos apresentou fluorescência no estado sólido e foram feitos estudos de suas propriedades fotofísicas e da sua interação com CT-DNA e BSA. Na terceira etapa do trabalho foram sintetizadas 5-bromo enamino ésteres e a partir desse intermediário foi possível a síntese de 3 heterociclos de forma seletiva, variando solvente, temperatura e base adicionada. Utilizando bases inorgânicas foi possível a síntese de furanos com até 85% de rendimento. Quando submetidos em reações com aminas primárias, foi obtido um caminho reacional seletivo para a formação de pirróis com até 93% de rendimento, e piperazin-2-onas com rendimentos 91% de rendimento. Os heterociclos desenvolvidos neste trabalho apresentam estruturas análogas à compostos com atividade biológica, sendo interessante o estudo de suas propriedades. As estruturas dos compostos foram elucidadas por experimentos de RMN de 1H, 13C, análises de RMN de 2D assim como experimentos raios-X.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESFundação de Amparo à Pesquisa do Estado do Rio Grande do Sul - FAPERGSporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccess4-alcoxi-5-bromo-1,1,1-trialopent-3-en-2-onasAminoácidosHeterociclosMorfolin-2-onasBenzoxazepinonasFuranosPirróisPiperazin-2-onas4-alkoxy-5-bromo-1,1,1-trialopent-3-en-2-onesAmino acidsHeterocyclesMorpholin-2-onesBenzoxazepinonesFuransPyrrolesPiperazin-2-onesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAReações entre (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas e aminoácidos para produção de heterociclos de 5, 6 e 7 membrosReactions of (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas and amino acids for the production of heterocycles with 5, 6 and 7 membersinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Frizzo, Clarissa PiccininIglesias, Bernardo AlmeidaStein, André Luiz AgnesGodoi, Benhur deGodoi, Marcelo dehttp://lattes.cnpq.br/3215982010548240Camargo, Adriano Felin100600000000600600600600600600600600233dc1de-ab03-4f57-9b85-e40dc01a2d4f085f5202-352a-4525-bd35-02020baeb1bb34c6d2e6-1cc5-4638-a14a-6ba61387c7d8483d6d0c-e419-454b-b413-1a51673258c38ea16b8c-d9d8-4c59-acd8-5ef92b79c155cf146591-5ab0-45b3-ba9e-06509120448f7adc234a-9c95-4865-880c-d879a3c65fe7reponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMLICENSElicense.txtlicense.txttext/plain; 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dc.title.por.fl_str_mv |
Reações entre (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas e aminoácidos para produção de heterociclos de 5, 6 e 7 membros |
dc.title.alternative.eng.fl_str_mv |
Reactions of (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas and amino acids for the production of heterocycles with 5, 6 and 7 members |
title |
Reações entre (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas e aminoácidos para produção de heterociclos de 5, 6 e 7 membros |
spellingShingle |
Reações entre (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas e aminoácidos para produção de heterociclos de 5, 6 e 7 membros Camargo, Adriano Felin 4-alcoxi-5-bromo-1,1,1-trialopent-3-en-2-onas Aminoácidos Heterociclos Morfolin-2-onas Benzoxazepinonas Furanos Pirróis Piperazin-2-onas 4-alkoxy-5-bromo-1,1,1-trialopent-3-en-2-ones Amino acids Heterocycles Morpholin-2-ones Benzoxazepinones Furans Pyrroles Piperazin-2-ones CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Reações entre (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas e aminoácidos para produção de heterociclos de 5, 6 e 7 membros |
title_full |
Reações entre (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas e aminoácidos para produção de heterociclos de 5, 6 e 7 membros |
title_fullStr |
Reações entre (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas e aminoácidos para produção de heterociclos de 5, 6 e 7 membros |
title_full_unstemmed |
Reações entre (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas e aminoácidos para produção de heterociclos de 5, 6 e 7 membros |
title_sort |
Reações entre (e)-5-bromo-1,1,1-trialo-4-metoxipent-3-en-2-onas e aminoácidos para produção de heterociclos de 5, 6 e 7 membros |
author |
Camargo, Adriano Felin |
author_facet |
Camargo, Adriano Felin |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Zanatta, Nilo |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.advisor-co1.fl_str_mv |
Frizzo, Clarissa Piccinin |
dc.contributor.referee1.fl_str_mv |
Iglesias, Bernardo Almeida |
dc.contributor.referee2.fl_str_mv |
Stein, André Luiz Agnes |
dc.contributor.referee3.fl_str_mv |
Godoi, Benhur de |
dc.contributor.referee4.fl_str_mv |
Godoi, Marcelo de |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3215982010548240 |
dc.contributor.author.fl_str_mv |
Camargo, Adriano Felin |
contributor_str_mv |
Zanatta, Nilo Frizzo, Clarissa Piccinin Iglesias, Bernardo Almeida Stein, André Luiz Agnes Godoi, Benhur de Godoi, Marcelo de |
dc.subject.por.fl_str_mv |
4-alcoxi-5-bromo-1,1,1-trialopent-3-en-2-onas Aminoácidos Heterociclos Morfolin-2-onas Benzoxazepinonas Furanos Pirróis Piperazin-2-onas |
topic |
4-alcoxi-5-bromo-1,1,1-trialopent-3-en-2-onas Aminoácidos Heterociclos Morfolin-2-onas Benzoxazepinonas Furanos Pirróis Piperazin-2-onas 4-alkoxy-5-bromo-1,1,1-trialopent-3-en-2-ones Amino acids Heterocycles Morpholin-2-ones Benzoxazepinones Furans Pyrroles Piperazin-2-ones CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
4-alkoxy-5-bromo-1,1,1-trialopent-3-en-2-ones Amino acids Heterocycles Morpholin-2-ones Benzoxazepinones Furans Pyrroles Piperazin-2-ones |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work present the versatility of 4-alkoxy-5-bromo-1,1,1-trialopent-3-en-2-ones in reactions with amino acids, exploring the four reactive centers of this building block and leading to the formation of heterocycles of 5, 6 and 7 members. Initially, a regioselective protocol was developed, using α-amino acids free of protecting groups, in one-pot reactions to obtain enantiomerically pure morpholin-2-ones. The reaction was selective for the formation of the Z regioisomer in all cases, however when a secondary amino group was used, only the E isomer was observed. The synthesized compounds were obtained in up to 92% yields. In the second step, the protocol previously developed was treated with β-amino acids derived from 4 and 5 substituted 2-aminobenzoic acids affording the corresponding of 7-membered heterocycles, benzoxazepinones, with up to 86% yields. These series of compounds showed solid state fluorescence and studies were carried out on their photophysical properties and their interaction with CT-DNA and BSA. In the third stage of the work, a series of 5-bromo enamino esters were synthesized, wich where used as intermediate for the synthesis of 3 differents heterocycles; in this regard, a séries of reaction parameters were evaluated incluiding, solvent, temperature and base. For instance using inorganic bases it was possible to synthesize furans with up to 85% yield. With primary amines, a selective reaction pathway was obtained for the formation of pyrroles with up to 93% yield, and piperazin-2-ones with 91% yield. The heterocycles developed in this work have structures similar to compounds with biological activity, making it interesting to study their properties. The structures of the compounds were elucidated by 1H, 13C NMR experiments, 2D NMR analyzes as well as X-ray experiments. |
publishDate |
2022 |
dc.date.accessioned.fl_str_mv |
2022-08-11T13:23:07Z |
dc.date.available.fl_str_mv |
2022-08-11T13:23:07Z |
dc.date.issued.fl_str_mv |
2022-05-13 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/25863 |
url |
http://repositorio.ufsm.br/handle/1/25863 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 600 600 |
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Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
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