Síntese de compostos contendo núcleos de pirimidínicos derivados de β-enaminodicetonas
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Repositório Institucional Manancial UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/20807 |
Resumo: | In this work the reactivity of β-enaminodiketones [RC(O)C(=CHNMe2)C(O)R1], (wher R= C6H5, 4-Me-C6H4, 4-OMe-C6H4, 4-Cl-C6H4 4-NO2-C6H4, thien-2-yl and furan-2-yl) and R1 (CF3 and CO2Et), was studied with dinucleophiles such as: N-substituted 2-methylisothiourea sulfates, 3-amino-1H-(1,2,4)-triazoles, and 2-aminobenzimidazole. The novel 5-trifluoromethyl[1,2,4]triazolo[1,5-a]pyrimidines were obtained in a highly regioselective manner from the cyclocondensation reaction between β-enaminodike-tones and 3-amino-triazoles in good yields. (72-90%). Then, the β-enaminodiketones were cyclocondensed with different 2-methylisothiurea sulfates, with the general for-mula [R1NHC(SMe)NH]2.H2SO4 where (R1= Me, Et, Ally). The pyrimidines were obtai-ned with high regioselectivity, and good yield (81-95%), when the reaction was perfor-med in basic medium using chloroform as the solvent. In this same reaction when the solvent was changed to acetonitrile, the elimination of the CF3 group occurred, thus obtaining the pyrimidinones in good yields (65-87%). Dihydrobenzo[4,5]imido[1,2-a]pyrimidines were selectively obtained through the reaction of β-enaminodecetones with 2-aminobenzimidazole, furnishing the expected products in good yields (87-98%), Finally, Benzo[4,5]imido [1,2-a]pyrimidines carboxylates were obtained in high purity and excellent yields (90 to 97%). The novel heterocycles obtained in this work were characterized by Hydrogen and Carbon Nuclear Magnetic Resonance, HMBC two-di-mensional NMR, Mass Spectrometry, Elemental Analysis and X-ray Diffraction. |
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3913 |
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2021-05-07T10:13:52Z2021-05-07T10:13:52Z2019-03-22http://repositorio.ufsm.br/handle/1/20807In this work the reactivity of β-enaminodiketones [RC(O)C(=CHNMe2)C(O)R1], (wher R= C6H5, 4-Me-C6H4, 4-OMe-C6H4, 4-Cl-C6H4 4-NO2-C6H4, thien-2-yl and furan-2-yl) and R1 (CF3 and CO2Et), was studied with dinucleophiles such as: N-substituted 2-methylisothiourea sulfates, 3-amino-1H-(1,2,4)-triazoles, and 2-aminobenzimidazole. The novel 5-trifluoromethyl[1,2,4]triazolo[1,5-a]pyrimidines were obtained in a highly regioselective manner from the cyclocondensation reaction between β-enaminodike-tones and 3-amino-triazoles in good yields. (72-90%). Then, the β-enaminodiketones were cyclocondensed with different 2-methylisothiurea sulfates, with the general for-mula [R1NHC(SMe)NH]2.H2SO4 where (R1= Me, Et, Ally). The pyrimidines were obtai-ned with high regioselectivity, and good yield (81-95%), when the reaction was perfor-med in basic medium using chloroform as the solvent. In this same reaction when the solvent was changed to acetonitrile, the elimination of the CF3 group occurred, thus obtaining the pyrimidinones in good yields (65-87%). Dihydrobenzo[4,5]imido[1,2-a]pyrimidines were selectively obtained through the reaction of β-enaminodecetones with 2-aminobenzimidazole, furnishing the expected products in good yields (87-98%), Finally, Benzo[4,5]imido [1,2-a]pyrimidines carboxylates were obtained in high purity and excellent yields (90 to 97%). The novel heterocycles obtained in this work were characterized by Hydrogen and Carbon Nuclear Magnetic Resonance, HMBC two-di-mensional NMR, Mass Spectrometry, Elemental Analysis and X-ray Diffraction.Neste trabalho foi analisada a reatividade de β-enaminodicetonas substituídas [RC(O)C(=CHNMe2)C(O)R1], (onde R = C6H5, 4-Me-C6H4, 4-OMe-C6H4, 4-Cl-C6H4, 4-Br-C6H4, 4-F-C6H4, 4-I-C6H4, 4-NO2-C6H4, tien-2-ila e furan-2-il) e R1(CF3 e CO2Et) frente a dinucleófilos como: sulfato de 2-metilisoureias, 3-amino-1H-(1,2,4)-triazóis 5-substituídos, e 2-aminobenzimidazol. As 5-trifluormetil[1,2,4]triazolo[1,5-a]pirimidinas inéditas foram obtidas de forma altamente regiosseletiva a partir da reação de ciclo-condensação entre β-enaminodicetonas com 3-amino-triazóis obtendo-se os produ-tos com bons rendimentos (72-90%). Em seguida, as β-enaminodicetonas foram ci-clocondensadas com diferentes sulfatos de 2-metilisotiureias N-substituídos, de fór-mula geral [R1NHC(SMe)NH]2.H2SO4 onde (R1= Me, Et, Alil) em meio básico, utili-zando como solvente clorofórmio, as pirimidinas trifluormetiladas foram obtidas com alta regiosseletividade, e bons rendimentos (81-95%). Nessa mesma reação quando se alterou o solvente para acetonitrila, ocorreu eliminação do grupo CF3, obtendo-se, assim, as pirimidinonas em bons rendimentos (65-87%). Diidrobenzo[4,5]imido[1,2-a]pirimidinas trifluormetiladas formam obtidas de forma seletiva, através da reação de β-enaminodicetonas e 2-aminobenzimidazol, resultando nos produtos esperados com bons rendimentos (87-98%), Para finalizar, Benzo[4,5]imido[1,2a]pirimidinas carboxi-latos foram obtidas com alto grau de pureza e rendimentos que variaram de 90 a 97%. Os heterociclos inéditos obtidos nesse trabalho foram caracterizados por Ressonância Magnética Nuclear de hidrogênio e Carbono, RMN bidimensional HMBC, Espectro-metria de Massas, Analise Elementar e Difratometria de Raio-X.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade 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/openAccessβ-enaminodicetonasCiclocondensaçãoTriazolopirimidinasPirimidinasβ-enaminodicetonesCyclocondensationTriazolopyrimidinesPyrimidinesDi-hydropyridinesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de compostos contendo núcleos de pirimidínicos derivados de β-enaminodicetonasSynthesis of compounds containing pyrimidine scafolds ob-tained from β-enaminodycetonesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Frizzo, Clarissa PiccininXXXXXXXXXXXXXXXRodrigues, Oscar Endrigo DornelesXXXXXXXXXXXXXXFantinel, LeonardoXXXXXXXXXXXXLüdtke, Diogo SeibertXXXXXXXXXXXXXXXhttp://lattes.cnpq.br/7060030192559964Andrade, Valquiria Pereira de100600000000600233dc1de-ab03-4f57-9b85-e40dc01a2d4f05641f8f-b910-49f6-93cf-d4256a812e17bf4338e5-e87c-4326-93b7-60f8f505f466f0970438-aab7-4bbe-8d26-13140ae7303aeba5e7a6-11ae-4c8d-8467-992f3d7d46e64ad25453-3697-4543-8bb8-1f5a9ec434c2reponame:Repositório Institucional Manancial UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2019_ANDRADE_VALQUIRIA.pdfTES_PPGQUIMICA_2019_ANDRADE_VALQUIRIA.pdfTese de Doutoradoapplication/pdf17827589http://repositorio.ufsm.br/bitstream/1/20807/1/TES_PPGQUIMICA_2019_ANDRADE_VALQUIRIA.pdff092f4e27056887f6499b77f16dea2cbMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese de compostos contendo núcleos de pirimidínicos derivados de β-enaminodicetonas |
dc.title.alternative.eng.fl_str_mv |
Synthesis of compounds containing pyrimidine scafolds ob-tained from β-enaminodycetones |
title |
Síntese de compostos contendo núcleos de pirimidínicos derivados de β-enaminodicetonas |
spellingShingle |
Síntese de compostos contendo núcleos de pirimidínicos derivados de β-enaminodicetonas Andrade, Valquiria Pereira de β-enaminodicetonas Ciclocondensação Triazolopirimidinas Pirimidinas β-enaminodicetones Cyclocondensation Triazolopyrimidines Pyrimidines Di-hydropyridines CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de compostos contendo núcleos de pirimidínicos derivados de β-enaminodicetonas |
title_full |
Síntese de compostos contendo núcleos de pirimidínicos derivados de β-enaminodicetonas |
title_fullStr |
Síntese de compostos contendo núcleos de pirimidínicos derivados de β-enaminodicetonas |
title_full_unstemmed |
Síntese de compostos contendo núcleos de pirimidínicos derivados de β-enaminodicetonas |
title_sort |
Síntese de compostos contendo núcleos de pirimidínicos derivados de β-enaminodicetonas |
author |
Andrade, Valquiria Pereira de |
author_facet |
Andrade, Valquiria Pereira de |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Zanatta, Nilo |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.referee1.fl_str_mv |
Frizzo, Clarissa Piccinin |
dc.contributor.referee1Lattes.fl_str_mv |
XXXXXXXXXXXXXXX |
dc.contributor.referee2.fl_str_mv |
Rodrigues, Oscar Endrigo Dorneles |
dc.contributor.referee2Lattes.fl_str_mv |
XXXXXXXXXXXXXX |
dc.contributor.referee3.fl_str_mv |
Fantinel, Leonardo |
dc.contributor.referee3Lattes.fl_str_mv |
XXXXXXXXXXXX |
dc.contributor.referee4.fl_str_mv |
Lüdtke, Diogo Seibert |
dc.contributor.referee4Lattes.fl_str_mv |
XXXXXXXXXXXXXXX |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/7060030192559964 |
dc.contributor.author.fl_str_mv |
Andrade, Valquiria Pereira de |
contributor_str_mv |
Zanatta, Nilo Frizzo, Clarissa Piccinin Rodrigues, Oscar Endrigo Dorneles Fantinel, Leonardo Lüdtke, Diogo Seibert |
dc.subject.por.fl_str_mv |
β-enaminodicetonas Ciclocondensação Triazolopirimidinas Pirimidinas |
topic |
β-enaminodicetonas Ciclocondensação Triazolopirimidinas Pirimidinas β-enaminodicetones Cyclocondensation Triazolopyrimidines Pyrimidines Di-hydropyridines CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
β-enaminodicetones Cyclocondensation Triazolopyrimidines Pyrimidines Di-hydropyridines |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this work the reactivity of β-enaminodiketones [RC(O)C(=CHNMe2)C(O)R1], (wher R= C6H5, 4-Me-C6H4, 4-OMe-C6H4, 4-Cl-C6H4 4-NO2-C6H4, thien-2-yl and furan-2-yl) and R1 (CF3 and CO2Et), was studied with dinucleophiles such as: N-substituted 2-methylisothiourea sulfates, 3-amino-1H-(1,2,4)-triazoles, and 2-aminobenzimidazole. The novel 5-trifluoromethyl[1,2,4]triazolo[1,5-a]pyrimidines were obtained in a highly regioselective manner from the cyclocondensation reaction between β-enaminodike-tones and 3-amino-triazoles in good yields. (72-90%). Then, the β-enaminodiketones were cyclocondensed with different 2-methylisothiurea sulfates, with the general for-mula [R1NHC(SMe)NH]2.H2SO4 where (R1= Me, Et, Ally). The pyrimidines were obtai-ned with high regioselectivity, and good yield (81-95%), when the reaction was perfor-med in basic medium using chloroform as the solvent. In this same reaction when the solvent was changed to acetonitrile, the elimination of the CF3 group occurred, thus obtaining the pyrimidinones in good yields (65-87%). Dihydrobenzo[4,5]imido[1,2-a]pyrimidines were selectively obtained through the reaction of β-enaminodecetones with 2-aminobenzimidazole, furnishing the expected products in good yields (87-98%), Finally, Benzo[4,5]imido [1,2-a]pyrimidines carboxylates were obtained in high purity and excellent yields (90 to 97%). The novel heterocycles obtained in this work were characterized by Hydrogen and Carbon Nuclear Magnetic Resonance, HMBC two-di-mensional NMR, Mass Spectrometry, Elemental Analysis and X-ray Diffraction. |
publishDate |
2019 |
dc.date.issued.fl_str_mv |
2019-03-22 |
dc.date.accessioned.fl_str_mv |
2021-05-07T10:13:52Z |
dc.date.available.fl_str_mv |
2021-05-07T10:13:52Z |
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/1/20807 |
url |
http://repositorio.ufsm.br/handle/1/20807 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 |
dc.relation.authority.fl_str_mv |
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dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
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 |
reponame:Repositório Institucional Manancial UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
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Universidade Federal de Santa Maria (UFSM) |
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UFSM |
institution |
UFSM |
reponame_str |
Repositório Institucional Manancial UFSM |
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Repositório Institucional Manancial UFSM |
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