Síntese de 1,7-fenantrolinas e 7-aminoquinolinas trifluormetil substituídas
Ano de defesa: | 2010 |
---|---|
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: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/10464 |
Resumo: | This work, at first, describes the synthesis and characterization of new series of (Z,Z)-N,N -bis(oxotrifluoroalkenyl)-1,3-phenylenediamines by the addition/elimination reaction of β-alkoxyvinyl trifluoromethyl ketones with 1,3-phenylenediamine, in 47-91 % yields. The 4-alkyl[aryl(heteroaryl)]-4-alkoxy-1,1,1-trifluoro-3-alken-2-ones, of general formula F3C-C(O)-CH=C(R1)-OR where R = Me, Et and R1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-ClPh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furoyl, 2-thienyl, were obtained from trifluoroacetylation reactions of enolethers or acetals derived of acyclic ketones. Subsequently is reported the synthesis and characterization of new series of bis-trifluoromethyl substituted 1,7-phenanthrolines, from cyclization reactions of bis-enaminones in a strongly acidic medium (PPA) and absence of solvent, in 22-40 % yields, where for the first time two interesting manners of cyclization were observed, in the synthesis of two different angular structures. The products were identified as 2,8-bis(trifluoromethyl)-1,7-phenanthroline and 2,10-dialkyl(aryl)-4,8-(bis-trifluoromethyl)-1,7-phenanthrolines. The synthetic route used herein also allowed the isolation of new series of 7-aminoquinolines structures in 20-45 % yields. Compounds were characterized by 1H, 13C NMR spectroscopy, by Mass Spectrometry, their structures also were established by X-ray diffraction and their purity was confirmed by elemental analysis. |
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2017-05-252017-05-252010-02-26ANDRIGHETTO, Rosalia. Synthesis of trifluoromethyl substituted 1,7-phenanthrolines and 7-aminoquinolines. 2010. 206 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2010.http://repositorio.ufsm.br/handle/1/10464This work, at first, describes the synthesis and characterization of new series of (Z,Z)-N,N -bis(oxotrifluoroalkenyl)-1,3-phenylenediamines by the addition/elimination reaction of β-alkoxyvinyl trifluoromethyl ketones with 1,3-phenylenediamine, in 47-91 % yields. The 4-alkyl[aryl(heteroaryl)]-4-alkoxy-1,1,1-trifluoro-3-alken-2-ones, of general formula F3C-C(O)-CH=C(R1)-OR where R = Me, Et and R1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-ClPh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furoyl, 2-thienyl, were obtained from trifluoroacetylation reactions of enolethers or acetals derived of acyclic ketones. Subsequently is reported the synthesis and characterization of new series of bis-trifluoromethyl substituted 1,7-phenanthrolines, from cyclization reactions of bis-enaminones in a strongly acidic medium (PPA) and absence of solvent, in 22-40 % yields, where for the first time two interesting manners of cyclization were observed, in the synthesis of two different angular structures. The products were identified as 2,8-bis(trifluoromethyl)-1,7-phenanthroline and 2,10-dialkyl(aryl)-4,8-(bis-trifluoromethyl)-1,7-phenanthrolines. The synthetic route used herein also allowed the isolation of new series of 7-aminoquinolines structures in 20-45 % yields. Compounds were characterized by 1H, 13C NMR spectroscopy, by Mass Spectrometry, their structures also were established by X-ray diffraction and their purity was confirmed by elemental analysis.A presente dissertação inicialmente descreve a síntese e caracterização de uma nova série de (Z,Z)-N,N -bis(oxotrifluoralquenil)-1,3-fenilenodiaminas a partir da reação de adição/eliminação entre β-alcoxivinil trifluormetil cetonas e o dinucleófilo 1,3-fenilenodiamina, obtidas com rendimentos de 47-91 %. As 4-alcóxi-4-alquil[aril(heteroaril)]-1,1,1-triflúor-3-alquen-2-onas, de fórmula geral F3C-C(O)-CH=C(R1)-OR onde R = Me, Et e R1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-ClPh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furil, 2-tienil foram obtidas a partir de reações de trifluoracetilação de enoléteres ou de acetais derivados de cetonas acíclicas. Subsequentemente é relatada a síntese e caracterização de uma nova série de 1,7-fenantrolinas bis-trifluormetil substituídas, obtidas a partir da reação de termociclização das bis-enamino cetonas em meio ácido PPA (ácido polifosfórico) na ausência de solvente, com rendimentos de 22-40 %. Duas interessantes maneiras de ciclização foram observadas na síntese dos iprodutos 2,8-bis(trifluormetil)-1,7-fenantrolina e 2,10-di(alquil/aril)-4,8-bis(trifluormetil)-1,7-fenantrolinas. Nesta segunda etapa é descrita a síntese e caracterização de uma nova série 2-aril[alquil(heteroaril)]-4-trifluormetil-7-aminoquinolinas, obtidas como co-produtos das reações de termociclização das bis-enamino cetonas em meio ácido PPA, em rendimentos de 20-45 %. Os compostos foram caracterizados por experimentos de RMN de 1H, RMN de 13C {1H}, por Espectrometria de Massas, Difração de Raios-X e sua pureza comprovada por Análise Elementar.Conselho Nacional de Desenvolvimento Científico e Tecnológicoapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaQuímicaAcetaisFenilenodiaminasFarmacos naturaisIndústria farmacêuticaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 1,7-fenantrolinas e 7-aminoquinolinas trifluormetil substituídasSynthesis of trifluoromethyl substituted 1,7-phenanthrolines and 7-aminoquinolinesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0Flores, Alex Fabiani Clarohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0Dornelles, Lucianohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797177P9http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4131584P0Andrighetto, Rosalia10060000000040050050050050006c852ad-d805-43c3-99d6-93a6a86f507c720f190c-d3eb-473d-b34d-464c63eb95804d308e51-3866-4274-9e77-03644c9383df4a671e0c-bfb0-436b-bd8f-ab5645f4229einfo:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALANDRIGHETTO, ROSALIA.pdfapplication/pdf13655082http://repositorio.ufsm.br/bitstream/1/10464/1/ANDRIGHETTO%2c%20ROSALIA.pdf3ad02f7ae375abd58f8ada50b6a689daMD51TEXTANDRIGHETTO, ROSALIA.pdf.txtANDRIGHETTO, ROSALIA.pdf.txtExtracted texttext/plain244588http://repositorio.ufsm.br/bitstream/1/10464/2/ANDRIGHETTO%2c%20ROSALIA.pdf.txt112a00bfa0196a36d0cc541439e2a0dcMD52THUMBNAILANDRIGHETTO, ROSALIA.pdf.jpgANDRIGHETTO, ROSALIA.pdf.jpgIM Thumbnailimage/jpeg6162http://repositorio.ufsm.br/bitstream/1/10464/3/ANDRIGHETTO%2c%20ROSALIA.pdf.jpg7c2dc4bf90e6250d6ca64cb07e24f7d7MD531/104642017-07-25 12:03:28.423oai:repositorio.ufsm.br:1/10464Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2017-07-25T15:03:28Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de 1,7-fenantrolinas e 7-aminoquinolinas trifluormetil substituídas |
dc.title.alternative.eng.fl_str_mv |
Synthesis of trifluoromethyl substituted 1,7-phenanthrolines and 7-aminoquinolines |
title |
Síntese de 1,7-fenantrolinas e 7-aminoquinolinas trifluormetil substituídas |
spellingShingle |
Síntese de 1,7-fenantrolinas e 7-aminoquinolinas trifluormetil substituídas Andrighetto, Rosalia Química Acetais Fenilenodiaminas Farmacos naturais Indústria farmacêutica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 1,7-fenantrolinas e 7-aminoquinolinas trifluormetil substituídas |
title_full |
Síntese de 1,7-fenantrolinas e 7-aminoquinolinas trifluormetil substituídas |
title_fullStr |
Síntese de 1,7-fenantrolinas e 7-aminoquinolinas trifluormetil substituídas |
title_full_unstemmed |
Síntese de 1,7-fenantrolinas e 7-aminoquinolinas trifluormetil substituídas |
title_sort |
Síntese de 1,7-fenantrolinas e 7-aminoquinolinas trifluormetil substituídas |
author |
Andrighetto, Rosalia |
author_facet |
Andrighetto, Rosalia |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0 |
dc.contributor.referee1.fl_str_mv |
Flores, Alex Fabiani Claro |
dc.contributor.referee1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0 |
dc.contributor.referee2.fl_str_mv |
Dornelles, Luciano |
dc.contributor.referee2Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797177P9 |
dc.contributor.authorLattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4131584P0 |
dc.contributor.author.fl_str_mv |
Andrighetto, Rosalia |
contributor_str_mv |
Bonacorso, Helio Gauze Flores, Alex Fabiani Claro Dornelles, Luciano |
dc.subject.por.fl_str_mv |
Química Acetais Fenilenodiaminas Farmacos naturais Indústria farmacêutica |
topic |
Química Acetais Fenilenodiaminas Farmacos naturais Indústria farmacêutica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work, at first, describes the synthesis and characterization of new series of (Z,Z)-N,N -bis(oxotrifluoroalkenyl)-1,3-phenylenediamines by the addition/elimination reaction of β-alkoxyvinyl trifluoromethyl ketones with 1,3-phenylenediamine, in 47-91 % yields. The 4-alkyl[aryl(heteroaryl)]-4-alkoxy-1,1,1-trifluoro-3-alken-2-ones, of general formula F3C-C(O)-CH=C(R1)-OR where R = Me, Et and R1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-ClPh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furoyl, 2-thienyl, were obtained from trifluoroacetylation reactions of enolethers or acetals derived of acyclic ketones. Subsequently is reported the synthesis and characterization of new series of bis-trifluoromethyl substituted 1,7-phenanthrolines, from cyclization reactions of bis-enaminones in a strongly acidic medium (PPA) and absence of solvent, in 22-40 % yields, where for the first time two interesting manners of cyclization were observed, in the synthesis of two different angular structures. The products were identified as 2,8-bis(trifluoromethyl)-1,7-phenanthroline and 2,10-dialkyl(aryl)-4,8-(bis-trifluoromethyl)-1,7-phenanthrolines. The synthetic route used herein also allowed the isolation of new series of 7-aminoquinolines structures in 20-45 % yields. Compounds were characterized by 1H, 13C NMR spectroscopy, by Mass Spectrometry, their structures also were established by X-ray diffraction and their purity was confirmed by elemental analysis. |
publishDate |
2010 |
dc.date.issued.fl_str_mv |
2010-02-26 |
dc.date.accessioned.fl_str_mv |
2017-05-25 |
dc.date.available.fl_str_mv |
2017-05-25 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
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masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
ANDRIGHETTO, Rosalia. Synthesis of trifluoromethyl substituted 1,7-phenanthrolines and 7-aminoquinolines. 2010. 206 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2010. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10464 |
identifier_str_mv |
ANDRIGHETTO, Rosalia. Synthesis of trifluoromethyl substituted 1,7-phenanthrolines and 7-aminoquinolines. 2010. 206 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2010. |
url |
http://repositorio.ufsm.br/handle/1/10464 |
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por |
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Universidade Federal de Santa Maria |
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UFSM |
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Universidade Federal de Santa Maria |
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