Síntese de 2-fenil-3H-pirimidin-4-onas 6-metilsubstituídas e 4- trifluormetil-2-ureído pirimidinas
Ano de defesa: | 2009 |
---|---|
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
|
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/1/4171 |
Resumo: | This study was carried out in three parts: At first, three methods for the bromination of 6-alkylsubstituted 2-phenyl-3H-pyrimidin-4-ones was developed for the synthesis of: (i) a new series of 6-alkylsubstituted 5-bromo-2-phenyl-3H-pyrimidin-4-ones, (ii) a new series of 6-(1-bromoalkyl)-2-phenyl-3H-pyrimidin-4-ones, and (iii) e new series of 5-bromo-6-(1-bromoalkyl)-2-phenyl-3H-pyrimidin-4-ones. On the second part, the brominated pyrimidines obtained, were used to synthesize new 6-methylsubstituted 2-phenyl-3Hpyrimidin-4-ones from the reaction of the brominated pyrimidinones with primary and secondary amines, pyridine and sodium azide. On the third part, a new series of 5- e 6-substituted 4-trifluoromethyl-2-ureido pyrimidines was prepared, in good yields, from the cyclocondensation reaction of β- alkoxyvinyl-trifluoromethylketones substituted and dicyanodiamide. The products synthesized in this study were obtained in good yields and were characterized by GC-MS and 1H e 13C RMN spectroscopy. The purity of the products was assured by elemental analysis. Some compounds such as 5-bromo-2-phenyl-6-propyl-3H-pyrimidin-4-one, 5-bromo-6-(1- bromopropyl)-2-phenyl-3H-pyrimidin-4-one, 5-bromo-6-(1-bromobutyl)-2-phenyl-3H-pyrimidin-4-one, 6-(1-azidoethyl)-5-bromo-2-phenyl-3H-pyrimidin-4-one, 6-(1-azidopropyl)-5-bromo-2-phenyl-3H-pyrimidin-4-one, and 6-(1-azidobutyl)-5-bromo-2-phenyl-3H-pyrimidin-4-one, exhibited significant antimicrobial activity against some microorganisms, such as Candida albicans, Saccharomyces cerevisiae, Staphylococcus aureus, Salmonela, Klebsiela pneumonie among others. |
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2017-05-182017-05-182009-01-12FANTINEL, Leonardo. Synthesis of 6-methylsubstituted 2-phenyl-3H-pyrimidin-4-ones and 4-trifluoromethyl-2-ureido pyrimidines. 2009. 214 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2009.http://repositorio.ufsm.br/handle/1/4171This study was carried out in three parts: At first, three methods for the bromination of 6-alkylsubstituted 2-phenyl-3H-pyrimidin-4-ones was developed for the synthesis of: (i) a new series of 6-alkylsubstituted 5-bromo-2-phenyl-3H-pyrimidin-4-ones, (ii) a new series of 6-(1-bromoalkyl)-2-phenyl-3H-pyrimidin-4-ones, and (iii) e new series of 5-bromo-6-(1-bromoalkyl)-2-phenyl-3H-pyrimidin-4-ones. On the second part, the brominated pyrimidines obtained, were used to synthesize new 6-methylsubstituted 2-phenyl-3Hpyrimidin-4-ones from the reaction of the brominated pyrimidinones with primary and secondary amines, pyridine and sodium azide. On the third part, a new series of 5- e 6-substituted 4-trifluoromethyl-2-ureido pyrimidines was prepared, in good yields, from the cyclocondensation reaction of β- alkoxyvinyl-trifluoromethylketones substituted and dicyanodiamide. The products synthesized in this study were obtained in good yields and were characterized by GC-MS and 1H e 13C RMN spectroscopy. The purity of the products was assured by elemental analysis. Some compounds such as 5-bromo-2-phenyl-6-propyl-3H-pyrimidin-4-one, 5-bromo-6-(1- bromopropyl)-2-phenyl-3H-pyrimidin-4-one, 5-bromo-6-(1-bromobutyl)-2-phenyl-3H-pyrimidin-4-one, 6-(1-azidoethyl)-5-bromo-2-phenyl-3H-pyrimidin-4-one, 6-(1-azidopropyl)-5-bromo-2-phenyl-3H-pyrimidin-4-one, and 6-(1-azidobutyl)-5-bromo-2-phenyl-3H-pyrimidin-4-one, exhibited significant antimicrobial activity against some microorganisms, such as Candida albicans, Saccharomyces cerevisiae, Staphylococcus aureus, Salmonela, Klebsiela pneumonie among others.Este trabalho foi realizado em três etapas. Na primeira, foram desenvolvidos três métodos de bromação de 2-fenil-3H-pirimidin-4-onas 6-alquilsubstituídas para a obtenção de: (i) uma série inédita de 5-bromo-2-fenil-3H-pirimidin-4-onas 6-alquilsubstituídas, (ii) uma série inédita de 6-(1- bromoalquil)-2-fenil-3H-pirimidin-4-onas e (iii) uma série inédita de 5-bromo-6-(1-bromoalquil)-2-fenil-3H-pirimidin-4-onas. Na segunda etapa, as pirimidinas bromadas, obtidas na etapa anterior, foram utilizadas para sintetizar novas 2-fenil-3H-pirimidin-4-onas 6-metilsubstituídas através de reações das pirimidinonas bromadas com aminas primárias e secundárias, piridina e azida de sódio. Na terceira etapa, foi sintetizada uma nova série de 4-trifluormetil-2-ureído pirimidinas 5- e 6-substituídas a partir de reações de ciclocondensação entre -alcoxivinil-fluormetilcetonas substituídas e dicianodiamida. Os produtos sintetizados neste trabalho foram obtidos em bons rendimentos e foram caracterizados por CG-EM e RMN de 1H e 13C. A pureza dos produtos foi comprovada por análise elementar. Alguns compostos como 5-bromo-2-fenil-6-propil-3H-pirimidin-4-ona, 5-bromo-6-(1-bromopropil)-2-fenil-3H-pirimidin-4-ona, 5-bromo-6-(1-bromobutil)-2-fenil-3Hpirimidin-4-ona, 6-(1-azidoetil)-5-bromo-2-fenil-3H-pirimidin-4-ona, 6-(1- azidopropil)-5-bromo-2-fenil-3H-pirimidin-4-ona e 6-(1-azidobutil)-5-bromo-2-fenil-3H-pirimidin-4-ona, apresentaram atividade antimicrobiana significativa contra alguns microorganismos como Candida albicans, Saccharomyces cerevisiae, Staphylococcus aureus, Salmonela, Klebsiela pneumonie e outras.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaBenzamidine hydrochlorideBrominationDicianidiamidaPyrimidinonesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 2-fenil-3H-pirimidin-4-onas 6-metilsubstituídas e 4- trifluormetil-2-ureído pirimidinasSynthesis of 6-methylsubstituted 2-phenyl-3H-pyrimidin-4-ones and 4-trifluoromethyl-2-ureido pyrimidinesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Schneider, Paulo Henriquehttp://lattes.cnpq.br/9953361052942820Appelt, Helmoz Roseniaimhttp://lattes.cnpq.br/5360357766246970Dalcol, Ionara Irionhttp://lattes.cnpq.br/9769548819312192Flores, Alex Fabiani Clarohttp://lattes.cnpq.br/1159954352174167http://lattes.cnpq.br/3934644027018397Fantinel, Leonardo100600000000400300300300300500300233dc1de-ab03-4f57-9b85-e40dc01a2d4fabaf8e6f-61da-4cca-a80d-90ef5eea0bfc45261c66-d648-4472-9675-c315a838b7684684f279-563c-45a1-a01d-7d0ddd2378cb11b367fb-0eed-426e-9ab5-e42e52a8d09835e22973-1fef-4e56-b9e4-53097efb9b44info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALFANTINEL, LEONARDO.pdfapplication/pdf14431164http://repositorio.ufsm.br/bitstream/1/4171/1/FANTINEL%2c%20LEONARDO.pdff4cb73d51931aaf2b923c38adbed0997MD51TEXTFANTINEL, LEONARDO.pdf.txtFANTINEL, LEONARDO.pdf.txtExtracted texttext/plain180797http://repositorio.ufsm.br/bitstream/1/4171/2/FANTINEL%2c%20LEONARDO.pdf.txt1aef3a7c53ed5784f1a747e95e5f76c6MD52THUMBNAILFANTINEL, LEONARDO.pdf.jpgFANTINEL, LEONARDO.pdf.jpgIM Thumbnailimage/jpeg4861http://repositorio.ufsm.br/bitstream/1/4171/3/FANTINEL%2c%20LEONARDO.pdf.jpg0b151bfa4c895f818deee21b175a3f03MD531/41712023-04-25 08:48:13.513oai:repositorio.ufsm.br:1/4171Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2023-04-25T11:48:13Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de 2-fenil-3H-pirimidin-4-onas 6-metilsubstituídas e 4- trifluormetil-2-ureído pirimidinas |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 6-methylsubstituted 2-phenyl-3H-pyrimidin-4-ones and 4-trifluoromethyl-2-ureido pyrimidines |
title |
Síntese de 2-fenil-3H-pirimidin-4-onas 6-metilsubstituídas e 4- trifluormetil-2-ureído pirimidinas |
spellingShingle |
Síntese de 2-fenil-3H-pirimidin-4-onas 6-metilsubstituídas e 4- trifluormetil-2-ureído pirimidinas Fantinel, Leonardo Benzamidine hydrochloride Bromination Dicianidiamida Pyrimidinones CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 2-fenil-3H-pirimidin-4-onas 6-metilsubstituídas e 4- trifluormetil-2-ureído pirimidinas |
title_full |
Síntese de 2-fenil-3H-pirimidin-4-onas 6-metilsubstituídas e 4- trifluormetil-2-ureído pirimidinas |
title_fullStr |
Síntese de 2-fenil-3H-pirimidin-4-onas 6-metilsubstituídas e 4- trifluormetil-2-ureído pirimidinas |
title_full_unstemmed |
Síntese de 2-fenil-3H-pirimidin-4-onas 6-metilsubstituídas e 4- trifluormetil-2-ureído pirimidinas |
title_sort |
Síntese de 2-fenil-3H-pirimidin-4-onas 6-metilsubstituídas e 4- trifluormetil-2-ureído pirimidinas |
author |
Fantinel, Leonardo |
author_facet |
Fantinel, Leonardo |
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 |
Schneider, Paulo Henrique |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/9953361052942820 |
dc.contributor.referee2.fl_str_mv |
Appelt, Helmoz Roseniaim |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/5360357766246970 |
dc.contributor.referee3.fl_str_mv |
Dalcol, Ionara Irion |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/9769548819312192 |
dc.contributor.referee4.fl_str_mv |
Flores, Alex Fabiani Claro |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/1159954352174167 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3934644027018397 |
dc.contributor.author.fl_str_mv |
Fantinel, Leonardo |
contributor_str_mv |
Zanatta, Nilo Schneider, Paulo Henrique Appelt, Helmoz Roseniaim Dalcol, Ionara Irion Flores, Alex Fabiani Claro |
dc.subject.por.fl_str_mv |
Benzamidine hydrochloride Bromination Dicianidiamida Pyrimidinones |
topic |
Benzamidine hydrochloride Bromination Dicianidiamida Pyrimidinones CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This study was carried out in three parts: At first, three methods for the bromination of 6-alkylsubstituted 2-phenyl-3H-pyrimidin-4-ones was developed for the synthesis of: (i) a new series of 6-alkylsubstituted 5-bromo-2-phenyl-3H-pyrimidin-4-ones, (ii) a new series of 6-(1-bromoalkyl)-2-phenyl-3H-pyrimidin-4-ones, and (iii) e new series of 5-bromo-6-(1-bromoalkyl)-2-phenyl-3H-pyrimidin-4-ones. On the second part, the brominated pyrimidines obtained, were used to synthesize new 6-methylsubstituted 2-phenyl-3Hpyrimidin-4-ones from the reaction of the brominated pyrimidinones with primary and secondary amines, pyridine and sodium azide. On the third part, a new series of 5- e 6-substituted 4-trifluoromethyl-2-ureido pyrimidines was prepared, in good yields, from the cyclocondensation reaction of β- alkoxyvinyl-trifluoromethylketones substituted and dicyanodiamide. The products synthesized in this study were obtained in good yields and were characterized by GC-MS and 1H e 13C RMN spectroscopy. The purity of the products was assured by elemental analysis. Some compounds such as 5-bromo-2-phenyl-6-propyl-3H-pyrimidin-4-one, 5-bromo-6-(1- bromopropyl)-2-phenyl-3H-pyrimidin-4-one, 5-bromo-6-(1-bromobutyl)-2-phenyl-3H-pyrimidin-4-one, 6-(1-azidoethyl)-5-bromo-2-phenyl-3H-pyrimidin-4-one, 6-(1-azidopropyl)-5-bromo-2-phenyl-3H-pyrimidin-4-one, and 6-(1-azidobutyl)-5-bromo-2-phenyl-3H-pyrimidin-4-one, exhibited significant antimicrobial activity against some microorganisms, such as Candida albicans, Saccharomyces cerevisiae, Staphylococcus aureus, Salmonela, Klebsiela pneumonie among others. |
publishDate |
2009 |
dc.date.issued.fl_str_mv |
2009-01-12 |
dc.date.accessioned.fl_str_mv |
2017-05-18 |
dc.date.available.fl_str_mv |
2017-05-18 |
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.citation.fl_str_mv |
FANTINEL, Leonardo. Synthesis of 6-methylsubstituted 2-phenyl-3H-pyrimidin-4-ones and 4-trifluoromethyl-2-ureido pyrimidines. 2009. 214 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2009. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/4171 |
identifier_str_mv |
FANTINEL, Leonardo. Synthesis of 6-methylsubstituted 2-phenyl-3H-pyrimidin-4-ones and 4-trifluoromethyl-2-ureido pyrimidines. 2009. 214 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2009. |
url |
http://repositorio.ufsm.br/handle/1/4171 |
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por |
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por |
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100600000000 |
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400 300 300 300 300 500 300 |
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Química |
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Universidade Federal de Santa Maria |
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