Compostos β-enamino carbonílicos: obtenção utilizando microondas, avaliação da sua reatividade e atividade antimicrobiana
Autor(a) principal: | |
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Data de Publicação: | 2007 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/4284 |
Resumo: | In this work, we explored new methodologies to obtain β-enamino carbonylic compounds derived from 1,3-dicarbonyl and α-amino acids using microwave and solvent free conditions. The β-enamino carbonylic compounds were prepared by the reaction of 1,3- dicarbonyl compounds, acetilacetone, ethyl acetoacetate or ethyl 2-oxo-1- cyclopentanecarboxylate with α-amino esters hydrochlorides derived from glycine, Lalanine, L-serine and L-proline. The reactions were performed with or without solid support (K-10 or KSF) using microwave irradiation. An addition aim of this study is the investigation of the reactivity of the β-enamino carbonylic compounds, with the possibility of creating alternative synthetic routes for heterocyclic compounds. The reactivity of the acyclic β-enamino carbonylic (C,N-dinucleophiles) was evaluated by reactions with the 1,2-diketones. To evaluate the influence of the group -CHR1COOEt (N- substituted) on the reactivity of the β-enamino carbonyl compounds obtained by reduction reactions, we used NaBH4/EtOH, which is effective for the selective reduction of the derived compounds of the acetilacetone or ethyl 2-oxo-1-cyclopentanecarboxylate giving their respective β-hidroxyenamino products. The reactivity of diethyl-3-benzylamino-2-pentenedioate was also evaluated using NaBH4, where the methylene acetate fragment (-CHR1COOEt), instead of being bonded to the nitrogen atom, is bonded to the β-carbon atom. This model allows us to evaluate the complexation of the nitrogen atom and carbonyl carbon atom with the tetrahydroborate and subsequent hydride transfer allowing a comparison with the reductions mentioned previously. The antimicrobial activity of the cyclic β-enamino carbonylic coumpounds, β- hydroxyenamino and of the heterocyclic 2-pyrrolin-5-one obtained, was investigated by the Bioautography method against different indicative microorganisms. |
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Compostos β-enamino carbonílicos: obtenção utilizando microondas, avaliação da sua reatividade e atividade antimicrobianaβ-enamino carbonylic compounds: obtaining using microwaves, evaluation of it s reactivity and antimicrobial activityMontmorillonitaMicroondasβ-enamino carbonílicosMicrowaveAtividade antimicrobianaMontmorilloniteβ-enamino carbonylic compoundsAntimicrobial activityCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAIn this work, we explored new methodologies to obtain β-enamino carbonylic compounds derived from 1,3-dicarbonyl and α-amino acids using microwave and solvent free conditions. The β-enamino carbonylic compounds were prepared by the reaction of 1,3- dicarbonyl compounds, acetilacetone, ethyl acetoacetate or ethyl 2-oxo-1- cyclopentanecarboxylate with α-amino esters hydrochlorides derived from glycine, Lalanine, L-serine and L-proline. The reactions were performed with or without solid support (K-10 or KSF) using microwave irradiation. An addition aim of this study is the investigation of the reactivity of the β-enamino carbonylic compounds, with the possibility of creating alternative synthetic routes for heterocyclic compounds. The reactivity of the acyclic β-enamino carbonylic (C,N-dinucleophiles) was evaluated by reactions with the 1,2-diketones. To evaluate the influence of the group -CHR1COOEt (N- substituted) on the reactivity of the β-enamino carbonyl compounds obtained by reduction reactions, we used NaBH4/EtOH, which is effective for the selective reduction of the derived compounds of the acetilacetone or ethyl 2-oxo-1-cyclopentanecarboxylate giving their respective β-hidroxyenamino products. The reactivity of diethyl-3-benzylamino-2-pentenedioate was also evaluated using NaBH4, where the methylene acetate fragment (-CHR1COOEt), instead of being bonded to the nitrogen atom, is bonded to the β-carbon atom. This model allows us to evaluate the complexation of the nitrogen atom and carbonyl carbon atom with the tetrahydroborate and subsequent hydride transfer allowing a comparison with the reductions mentioned previously. The antimicrobial activity of the cyclic β-enamino carbonylic coumpounds, β- hydroxyenamino and of the heterocyclic 2-pyrrolin-5-one obtained, was investigated by the Bioautography method against different indicative microorganisms.Coordenação de Aperfeiçoamento de Pessoal de Nível SuperiorNeste trabalho buscamos estabelecer metodologias para obtenção de compostos β-enamino carbonílicos, derivados de 1,3-dicarbonílicos e α-aminoácidos utilizando energia de microondas e ausência de solvente. Os compostos β-enamino carbonílicos foram obtidos empregando compostos dicarbonílicos como acetilacetona ou acetoacetato de etila ou 2-oxo-1-ciclopentanocarboxilato de etila com cloridratos de α-aminoésteres derivados da glicina, Lalanina, L-serina e L-prolina. Estes compostos foram obtidos empregando reações em forno de microondas doméstico associado ou não a suporte sólido (K-10 ou KSF). Nossos estudos também tem por objetivo uma aplicação imediata na investigação da reatividade dos sistemas β-enamino carbonílicos obtidos, visualizando a possibilidade de criarmos rotas alternativas para obtenção de compostos heterocíclicos. Portanto, neste trabalho, com o propósito de obter compostos N-heterociclos, avaliou-se a reatividade dos β-enamino carbonílicos acíclicos (C,N-dinucleófilos), através de reações com 1,2-dicetonas. Com o intuito de avaliarmos a influência do grupo -CHR1COOEt (N-funcionalizado) na reatividade dos β-enamino carbonílicos obtidos em reações de redução, empregamos NaBH4/EtOH, o qual foi efetivo na redução seletiva dos compostos derivados da acetilacetona e 2-oxo-1-ciclopentanocarboxilato de etila levando a obtenção dos respectivos β-hidroxienaminos. A reatividade do composto 3- benzilamino-2-pentenodioato de dietila também foi avaliada utilizando NaBH4, onde o fragmento metileno acetato (-CHR1COOEt), ao invés de estar ligado ao Nitrogênio está ligado ao carbono β. Este modelo nos permite avaliar a complexação do Nitrogênio e da carbonila com o tetrahidroborato e posterior transfência do hidreto possibilitando estabelecer uma comparação com as reduções efetuadas anteriormente. A investigação da atividade antimicrobiana dos compostos cíclicos como os β-enamino carbonílicos, β-hidroxienaminos e do heterociclo 2-pirrolin-5-ona obtidos neste trabalho, foi realizada através do método de Bioautografia, frente a diferentes microorganismos indicadores.Universidade Federal de Santa MariaBRQuímicaUFSMPrograma de Pós-Graduação em QuímicaBraibante, Mara Elisa Forteshttp://lattes.cnpq.br/0685197822607977Cunha, Silvio do Desterrohttp://lattes.cnpq.br/5661286013847300Morel, Ademir Fariashttp://lattes.cnpq.br/3554994385525333Bonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Marques, Miriam InesCosta, Carla Cristiane2017-05-112017-05-112007-05-10info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisapplication/pdfapplication/pdfCOSTA, Carla Cristiane. β-enamino carbonylic compounds: obtaining using microwaves, evaluation of it s reactivity and antimicrobial activity. 2007. 199 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007.http://repositorio.ufsm.br/handle/1/4284porinfo:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSM2023-01-05T11:38:06Zoai:repositorio.ufsm.br:1/4284Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2023-01-05T11:38:06Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.none.fl_str_mv |
Compostos β-enamino carbonílicos: obtenção utilizando microondas, avaliação da sua reatividade e atividade antimicrobiana β-enamino carbonylic compounds: obtaining using microwaves, evaluation of it s reactivity and antimicrobial activity |
title |
Compostos β-enamino carbonílicos: obtenção utilizando microondas, avaliação da sua reatividade e atividade antimicrobiana |
spellingShingle |
Compostos β-enamino carbonílicos: obtenção utilizando microondas, avaliação da sua reatividade e atividade antimicrobiana Costa, Carla Cristiane Montmorillonita Microondas β-enamino carbonílicos Microwave Atividade antimicrobiana Montmorillonite β-enamino carbonylic compounds Antimicrobial activity CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Compostos β-enamino carbonílicos: obtenção utilizando microondas, avaliação da sua reatividade e atividade antimicrobiana |
title_full |
Compostos β-enamino carbonílicos: obtenção utilizando microondas, avaliação da sua reatividade e atividade antimicrobiana |
title_fullStr |
Compostos β-enamino carbonílicos: obtenção utilizando microondas, avaliação da sua reatividade e atividade antimicrobiana |
title_full_unstemmed |
Compostos β-enamino carbonílicos: obtenção utilizando microondas, avaliação da sua reatividade e atividade antimicrobiana |
title_sort |
Compostos β-enamino carbonílicos: obtenção utilizando microondas, avaliação da sua reatividade e atividade antimicrobiana |
author |
Costa, Carla Cristiane |
author_facet |
Costa, Carla Cristiane |
author_role |
author |
dc.contributor.none.fl_str_mv |
Braibante, Mara Elisa Fortes http://lattes.cnpq.br/0685197822607977 Cunha, Silvio do Desterro http://lattes.cnpq.br/5661286013847300 Morel, Ademir Farias http://lattes.cnpq.br/3554994385525333 Bonacorso, Helio Gauze http://lattes.cnpq.br/7275608974248322 Marques, Miriam Ines |
dc.contributor.author.fl_str_mv |
Costa, Carla Cristiane |
dc.subject.por.fl_str_mv |
Montmorillonita Microondas β-enamino carbonílicos Microwave Atividade antimicrobiana Montmorillonite β-enamino carbonylic compounds Antimicrobial activity CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Montmorillonita Microondas β-enamino carbonílicos Microwave Atividade antimicrobiana Montmorillonite β-enamino carbonylic compounds Antimicrobial activity CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this work, we explored new methodologies to obtain β-enamino carbonylic compounds derived from 1,3-dicarbonyl and α-amino acids using microwave and solvent free conditions. The β-enamino carbonylic compounds were prepared by the reaction of 1,3- dicarbonyl compounds, acetilacetone, ethyl acetoacetate or ethyl 2-oxo-1- cyclopentanecarboxylate with α-amino esters hydrochlorides derived from glycine, Lalanine, L-serine and L-proline. The reactions were performed with or without solid support (K-10 or KSF) using microwave irradiation. An addition aim of this study is the investigation of the reactivity of the β-enamino carbonylic compounds, with the possibility of creating alternative synthetic routes for heterocyclic compounds. The reactivity of the acyclic β-enamino carbonylic (C,N-dinucleophiles) was evaluated by reactions with the 1,2-diketones. To evaluate the influence of the group -CHR1COOEt (N- substituted) on the reactivity of the β-enamino carbonyl compounds obtained by reduction reactions, we used NaBH4/EtOH, which is effective for the selective reduction of the derived compounds of the acetilacetone or ethyl 2-oxo-1-cyclopentanecarboxylate giving their respective β-hidroxyenamino products. The reactivity of diethyl-3-benzylamino-2-pentenedioate was also evaluated using NaBH4, where the methylene acetate fragment (-CHR1COOEt), instead of being bonded to the nitrogen atom, is bonded to the β-carbon atom. This model allows us to evaluate the complexation of the nitrogen atom and carbonyl carbon atom with the tetrahydroborate and subsequent hydride transfer allowing a comparison with the reductions mentioned previously. The antimicrobial activity of the cyclic β-enamino carbonylic coumpounds, β- hydroxyenamino and of the heterocyclic 2-pyrrolin-5-one obtained, was investigated by the Bioautography method against different indicative microorganisms. |
publishDate |
2007 |
dc.date.none.fl_str_mv |
2007-05-10 2017-05-11 2017-05-11 |
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 |
COSTA, Carla Cristiane. β-enamino carbonylic compounds: obtaining using microwaves, evaluation of it s reactivity and antimicrobial activity. 2007. 199 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007. http://repositorio.ufsm.br/handle/1/4284 |
identifier_str_mv |
COSTA, Carla Cristiane. β-enamino carbonylic compounds: obtaining using microwaves, evaluation of it s reactivity and antimicrobial activity. 2007. 199 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007. |
url |
http://repositorio.ufsm.br/handle/1/4284 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria BR Química UFSM Programa de Pós-Graduação em Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria BR Química UFSM Programa de Pós-Graduação em Química |
dc.source.none.fl_str_mv |
reponame:Manancial - Repositório Digital da UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Manancial - Repositório Digital da UFSM |
collection |
Manancial - Repositório Digital da UFSM |
repository.name.fl_str_mv |
Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1805922172497035264 |