Síntese, reatividade e atividade antimicrobiana de β-enamino ésteres α-clorados utilizando K-10 e irradiação de microondas
Ano de defesa: | 2005 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
|
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
BR
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/10393 |
Resumo: | Enamino carbonylic compounds are important synthetic intermediates used in the synthesis of heterocycles and natural products. Our group of research has been dedicating much of our efforts to the development and implementation of simple and efficient methodologies to obtain β-enamino carbonylic compounds, mainly due to their functionality and ability to react both as ambident nucleophiles and as ambident electrophiles. In this dissertation, we study the synthesis and reactivity of new α-chloro functionalized N-substituted β-enamino acyclic compounds. In the synthesis of α-chlorinated β-enamino esters (2a-g) was employed the condensation of ethyl 2-chloro-acetoacetate with primary amines. This convenient and safe procedure uses the clean chemistry methodology of microwave-assisted solid support (K-10) synthesis in the absence of solvent. The reactivity and regiochemistry of the α-chlorinated β-enamino compounds was assessed through the study of cyclization reactions involving the coupling of these substrates with dinucleophiles such as hydrazine and semicarbazide derivatives. The obtained heterocycles showed the influence of the chloro substituent at the α position, which led to the inversion of reactivity of this center, allowing the preparation of heterocyclic compounds having four and six members. These functionalized heterocycle derivatives are attractive targets for the discovery of new active molecules as they have high potential to present a broad range of biological properties. Therefore, evaluation of the antimicrobial activity of the newly synthesized compounds was carried out using the in vitro Bioautography assay. |
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2017-05-122017-05-122005-12-15ORIQUES, Daniela Alves. Synthesis, reactivity and antimicrobial activity of α-chloro β-enamino esters using K-10 and microwave irradiation. 2005. 81 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2005.http://repositorio.ufsm.br/handle/1/10393Enamino carbonylic compounds are important synthetic intermediates used in the synthesis of heterocycles and natural products. Our group of research has been dedicating much of our efforts to the development and implementation of simple and efficient methodologies to obtain β-enamino carbonylic compounds, mainly due to their functionality and ability to react both as ambident nucleophiles and as ambident electrophiles. In this dissertation, we study the synthesis and reactivity of new α-chloro functionalized N-substituted β-enamino acyclic compounds. In the synthesis of α-chlorinated β-enamino esters (2a-g) was employed the condensation of ethyl 2-chloro-acetoacetate with primary amines. This convenient and safe procedure uses the clean chemistry methodology of microwave-assisted solid support (K-10) synthesis in the absence of solvent. The reactivity and regiochemistry of the α-chlorinated β-enamino compounds was assessed through the study of cyclization reactions involving the coupling of these substrates with dinucleophiles such as hydrazine and semicarbazide derivatives. The obtained heterocycles showed the influence of the chloro substituent at the α position, which led to the inversion of reactivity of this center, allowing the preparation of heterocyclic compounds having four and six members. These functionalized heterocycle derivatives are attractive targets for the discovery of new active molecules as they have high potential to present a broad range of biological properties. Therefore, evaluation of the antimicrobial activity of the newly synthesized compounds was carried out using the in vitro Bioautography assay.Compostos enamino carbonílicos são importantes intermediários sintéticos usados na síntese de heterociclos e produtos naturais. Nosso grupo de pesquisa tem se dedicado ao desenvolvimento e implementação de metodologias simples e eficientes para obter compostos β-enamino carbonílicos, principalmente devido à sua funcionalidade, atuando como sistema ambidentado, tanto com caráter nucleofílico como eletrofílico. Neste trabalho, nós estudamos a síntese e a reatividade de novos β-enamino compostos acíclicos α-cloro funcionalizados Nsubstituídos. Na síntese de β-enamino ésteres α-clorados (2a-g) foi empregada a condensação do 2-cloro acetoacetato de etila com aminas primárias. Este procedimento simples e seguro, emprega a metodologia de suporte sólido (K-10) associada ao uso de energia de microondas (MO) na ausência de solvente, sendo considerado como um protocolo de Química Limpa. A reatividade dos centros eletrofílicos dos β-enamino compostos α-clorados foi estudada em reações de ciclização, reagindo-se estes compostos frente a dinucleófilos como hidrazinas e semicarbazida, avaliando-se o padrão de reatividade destes compostos e a regioquímica dos sistemas heterocíclicos polifuncionalizados 3 e 4 obtidos. Os heterociclos obtidos mostraram a influência do substituinte cloro na posição α, o qual levou a uma inversão na reatividade deste centro, possibilitando a obtenção de compostos heterocíclicos de quatro e seis membros. Os sistemas heterocíclicos funcionalizados obtidos são alvos atrativos para a descoberta de novas moléculas ativas, devido as suas características estruturais com elevado potencial para apresentar propriedades biológicas. Portanto, estudos foram conduzidos para determinar a atividade antimicrobiana de uma série de compostos sintetizados empregando o ensaio in vitro através do método de Bioautografia.Conselho Nacional de Desenvolvimento Científico e Tecnológicoapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaK-10Microondasβ-enamino ésteres α-cloradosHeterociclosMicrowaveα-chlorinated β-enamino estersHeterocyclesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese, reatividade e atividade antimicrobiana de β-enamino ésteres α-clorados utilizando K-10 e irradiação de microondasSynthesis, reactivity and antimicrobial activity of α-chloro β-enamino esters using K-10 and microwave irradiationinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBraibante, Mara Elisa Forteshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788627U5Morel, Ademir Fariashttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783930A8Marchi, Miriam Ineshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4761904P8Dalcol, Ionara Irionhttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797864E9http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4772280J8Oriques, Daniela Alves1006000000004005003005003005006e9d3171-46d3-4ee5-a0a1-ee7cd026f24b5c08870b-04e2-40d2-9adf-6b41d874a2a622df5f67-c304-4742-b982-4d1e6d30aecc04ca62b4-c920-4a5f-bee4-d041599f46ba11b367fb-0eed-426e-9ab5-e42e52a8d098info:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDANIELA ORIQUES.pdfapplication/pdf2590905http://repositorio.ufsm.br/bitstream/1/10393/1/DANIELA%20ORIQUES.pdf19ee06b90cedc1708c364accd0433771MD51TEXTDANIELA ORIQUES.pdf.txtDANIELA ORIQUES.pdf.txtExtracted texttext/plain113271http://repositorio.ufsm.br/bitstream/1/10393/2/DANIELA%20ORIQUES.pdf.txtcaaeb5fa42bcfcd875fcfd60f60af352MD52THUMBNAILDANIELA ORIQUES.pdf.jpgDANIELA ORIQUES.pdf.jpgIM Thumbnailimage/jpeg5025http://repositorio.ufsm.br/bitstream/1/10393/3/DANIELA%20ORIQUES.pdf.jpg88785c3ca6852a9f4bf06e2aee3fea56MD531/103932017-07-27 08:42:12.132oai:repositorio.ufsm.br:1/10393Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132017-07-27T11:42:12Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese, reatividade e atividade antimicrobiana de β-enamino ésteres α-clorados utilizando K-10 e irradiação de microondas |
dc.title.alternative.eng.fl_str_mv |
Synthesis, reactivity and antimicrobial activity of α-chloro β-enamino esters using K-10 and microwave irradiation |
title |
Síntese, reatividade e atividade antimicrobiana de β-enamino ésteres α-clorados utilizando K-10 e irradiação de microondas |
spellingShingle |
Síntese, reatividade e atividade antimicrobiana de β-enamino ésteres α-clorados utilizando K-10 e irradiação de microondas Oriques, Daniela Alves K-10 Microondas β-enamino ésteres α-clorados Heterociclos Microwave α-chlorinated β-enamino esters Heterocycles CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese, reatividade e atividade antimicrobiana de β-enamino ésteres α-clorados utilizando K-10 e irradiação de microondas |
title_full |
Síntese, reatividade e atividade antimicrobiana de β-enamino ésteres α-clorados utilizando K-10 e irradiação de microondas |
title_fullStr |
Síntese, reatividade e atividade antimicrobiana de β-enamino ésteres α-clorados utilizando K-10 e irradiação de microondas |
title_full_unstemmed |
Síntese, reatividade e atividade antimicrobiana de β-enamino ésteres α-clorados utilizando K-10 e irradiação de microondas |
title_sort |
Síntese, reatividade e atividade antimicrobiana de β-enamino ésteres α-clorados utilizando K-10 e irradiação de microondas |
author |
Oriques, Daniela Alves |
author_facet |
Oriques, Daniela Alves |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Braibante, Mara Elisa Fortes |
dc.contributor.advisor1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788627U5 |
dc.contributor.referee1.fl_str_mv |
Morel, Ademir Farias |
dc.contributor.referee1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783930A8 |
dc.contributor.referee2.fl_str_mv |
Marchi, Miriam Ines |
dc.contributor.referee2Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4761904P8 |
dc.contributor.referee3.fl_str_mv |
Dalcol, Ionara Irion |
dc.contributor.referee3Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797864E9 |
dc.contributor.authorLattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4772280J8 |
dc.contributor.author.fl_str_mv |
Oriques, Daniela Alves |
contributor_str_mv |
Braibante, Mara Elisa Fortes Morel, Ademir Farias Marchi, Miriam Ines Dalcol, Ionara Irion |
dc.subject.por.fl_str_mv |
K-10 Microondas β-enamino ésteres α-clorados Heterociclos |
topic |
K-10 Microondas β-enamino ésteres α-clorados Heterociclos Microwave α-chlorinated β-enamino esters Heterocycles CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Microwave α-chlorinated β-enamino esters Heterocycles |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
Enamino carbonylic compounds are important synthetic intermediates used in the synthesis of heterocycles and natural products. Our group of research has been dedicating much of our efforts to the development and implementation of simple and efficient methodologies to obtain β-enamino carbonylic compounds, mainly due to their functionality and ability to react both as ambident nucleophiles and as ambident electrophiles. In this dissertation, we study the synthesis and reactivity of new α-chloro functionalized N-substituted β-enamino acyclic compounds. In the synthesis of α-chlorinated β-enamino esters (2a-g) was employed the condensation of ethyl 2-chloro-acetoacetate with primary amines. This convenient and safe procedure uses the clean chemistry methodology of microwave-assisted solid support (K-10) synthesis in the absence of solvent. The reactivity and regiochemistry of the α-chlorinated β-enamino compounds was assessed through the study of cyclization reactions involving the coupling of these substrates with dinucleophiles such as hydrazine and semicarbazide derivatives. The obtained heterocycles showed the influence of the chloro substituent at the α position, which led to the inversion of reactivity of this center, allowing the preparation of heterocyclic compounds having four and six members. These functionalized heterocycle derivatives are attractive targets for the discovery of new active molecules as they have high potential to present a broad range of biological properties. Therefore, evaluation of the antimicrobial activity of the newly synthesized compounds was carried out using the in vitro Bioautography assay. |
publishDate |
2005 |
dc.date.issued.fl_str_mv |
2005-12-15 |
dc.date.accessioned.fl_str_mv |
2017-05-12 |
dc.date.available.fl_str_mv |
2017-05-12 |
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.citation.fl_str_mv |
ORIQUES, Daniela Alves. Synthesis, reactivity and antimicrobial activity of α-chloro β-enamino esters using K-10 and microwave irradiation. 2005. 81 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2005. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10393 |
identifier_str_mv |
ORIQUES, Daniela Alves. Synthesis, reactivity and antimicrobial activity of α-chloro β-enamino esters using K-10 and microwave irradiation. 2005. 81 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2005. |
url |
http://repositorio.ufsm.br/handle/1/10393 |
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Universidade Federal de Santa Maria |
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Programa de Pós-Graduação em Química |
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