Bi-heterociclos a partir do Ácido Levulínico: Síntese de 5-[(5-(trifluormetil)-5-hidroxi-(3-substituido)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetil)pirazolo[1,5-a]pirimidinas

Detalhes bibliográficos
Ano de defesa: 2013
Autor(a) principal: Rosales, Pauline Fagundes lattes
Orientador(a): Flores, Alex Fabiani Claro lattes
Banca de defesa: Pereira, Claudio Martin Pereira de lattes, Rodrigues, Oscar Endrigo Dorneles lattes
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:
Pirazolo[1,5-a]pirimidinas
Pirazóis
Bi-heterociclos
Palavras-chave em Inglês:
Pyrazolo[1,5-a]pyrimidines
Pyrazoles
Bi-heterocyclic
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/10535
Resumo: An efficient method to obtain 2-methyl-5-(methylpropanoate-3-yl)-7-trifluoromethylpyrazolo[1,5-a]pyrimidine 2 from the reaction of compound methyl 7,7,7-trifluoro-4-methoxy-6-oxo-heptenoate with 3-amino-5-methyl-1H-pyrazol. This compound 2 brought to reaction with hydrazine monohydrate to obtain 2-methyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine-5-propanehydrazine 3 and after were later brought to cyclocondensation reaction with a series of β-alkoxyvinyltrifluoromethyl ketones giving the series of news bi-heterocyclic 5-[(5-(trifluoromethyl)-5-hydroxy- (3-substituted)-4,5-dihydro-1H-pyrazol-1-yl)-1-propan-1-one-3-yl]-2-methyl-7-trifluoro methyl)pyrazolo[1,5-a]pyrimidines compounds 5a-l. Compound 2-methyl-5-(methylpropanoate-3-yl)-7-trifluoromethylpyrazolo[1,5-a]pyrimidine 2 brought to transesterification reaction and hydrolises reaction for obtaining the compounds 6 and 7. The structures of all synthesized compounds were confirmed by 1H, 13C, 19F NMR data, and two-dimensional NMR techniques like HETCOR and COLOC, mass spectrometry data.
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spelling 2014-02-102014-02-102013-03-04ROSALES, Pauline Fagundes. From Levulinic Acid to Biheterocycles: Synthesis of 5-[(5-(trifluoromethyl)-5-hydroxy-(3-substituted)-4,5-dihydro-1H-pyrazol-1-yl)-1-propan-1-one-3-yl]-2-methyl-7-trifluoromethyl)pyrazolo [1,5-a]pyrimidines. 2013. 198 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013.http://repositorio.ufsm.br/handle/1/10535An efficient method to obtain 2-methyl-5-(methylpropanoate-3-yl)-7-trifluoromethylpyrazolo[1,5-a]pyrimidine 2 from the reaction of compound methyl 7,7,7-trifluoro-4-methoxy-6-oxo-heptenoate with 3-amino-5-methyl-1H-pyrazol. This compound 2 brought to reaction with hydrazine monohydrate to obtain 2-methyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine-5-propanehydrazine 3 and after were later brought to cyclocondensation reaction with a series of β-alkoxyvinyltrifluoromethyl ketones giving the series of news bi-heterocyclic 5-[(5-(trifluoromethyl)-5-hydroxy- (3-substituted)-4,5-dihydro-1H-pyrazol-1-yl)-1-propan-1-one-3-yl]-2-methyl-7-trifluoro methyl)pyrazolo[1,5-a]pyrimidines compounds 5a-l. Compound 2-methyl-5-(methylpropanoate-3-yl)-7-trifluoromethylpyrazolo[1,5-a]pyrimidine 2 brought to transesterification reaction and hydrolises reaction for obtaining the compounds 6 and 7. The structures of all synthesized compounds were confirmed by 1H, 13C, 19F NMR data, and two-dimensional NMR techniques like HETCOR and COLOC, mass spectrometry data.Este trabalho descreve um método eficiente para a obtenção de 2-metil-5-(propanoato-3-il de metila)-7-trifluormetilpirazolo[1,5-a]pirimidina 2 a partir da reação de ciclocondensação do composto 7,7,7-trifluor-4-metoxi-6-oxo-4-heptenoato de metila com 3-amino-5-metil-1H-pirazol. Este composto 2 foi levado à reação com monohidrato de hidrazina obtendo-se a 2-metil-7-trifluormetilpirazolo[1,5-a]pirimidina-5-propanohidrazina 3. Posteriormente, o composto 3 foi levado à reação de ciclocondensação do tipo [3+2] com uma série de β-alcoxivniltrifluormetil cetonas alquil e aril substituídas utilizando etanol como solvente, resultando em uma série de compostos bi-heterocíclicos inéditos 5-[(5-trifluormetil)-5-hidróxi-(3-substituidos)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetilpirazolo[1,5-a]pirimidina 5a-l. O composto 2-metil-5-(propanoato-3-il de metila)-7-trifluormetilpirazolo[1,5-a]pirimidina 2 foi levado à reação de transesterificação e à reação de hidrólise para a formação dos respectivos compostos 6 e 7. As estruturas de todos os compostos sintetizados foram confirmadas por dados de RMN 1H, 13C, 19F e técnicas de RMN bidimensionais como HETCOR e COLOC, além de dados de espectrometria de massas.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaPirazolo[1,5-a]pirimidinasPirazóisBi-heterociclosPyrazolo[1,5-a]pyrimidinesPyrazolesBi-heterocyclicCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICABi-heterociclos a partir do Ácido Levulínico: Síntese de 5-[(5-(trifluormetil)-5-hidroxi-(3-substituido)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetil)pirazolo[1,5-a]pirimidinasFrom Levulinic Acid to Biheterocycles: Synthesis of 5-[(5-(trifluoromethyl)-5-hydroxy-(3-substituted)-4,5-dihydro-1H-pyrazol-1-yl)-1-propan-1-one-3-yl]-2-methyl-7-trifluoromethyl)pyrazolo [1,5-a]pyrimidinesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisFlores, Alex Fabiani Clarohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0Pereira, Claudio Martin Pereira dehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4769201U4Rodrigues, Oscar Endrigo Dorneleshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4763956Z6http://lattes.cnpq.br/1677974893141092Rosales, Pauline Fagundes1006000000004005003003005008a4555ae-c246-4b1a-adac-bf3b2784da08f0596a5a-ad88-49b3-b225-dc833dafd09f2b5f78ba-b70a-4d4d-9764-ff8348dbec15f0970438-aab7-4bbe-8d26-13140ae7303ainfo:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALROSALES, PAULINE FAGUNDES.pdfapplication/pdf7514855http://repositorio.ufsm.br/bitstream/1/10535/1/ROSALES%2c%20PAULINE%20FAGUNDES.pdf611f0aaa7fa92feb29ad220a92b1a7deMD51TEXTROSALES, PAULINE FAGUNDES.pdf.txtROSALES, PAULINE FAGUNDES.pdf.txtExtracted texttext/plain147916http://repositorio.ufsm.br/bitstream/1/10535/2/ROSALES%2c%20PAULINE%20FAGUNDES.pdf.txt55248fe97ff1c27d02cdeb8c8395505fMD52THUMBNAILROSALES, PAULINE FAGUNDES.pdf.jpgROSALES, PAULINE FAGUNDES.pdf.jpgIM Thumbnailimage/jpeg6182http://repositorio.ufsm.br/bitstream/1/10535/3/ROSALES%2c%20PAULINE%20FAGUNDES.pdf.jpga74049cc09f772c8a7782a3c0560edbdMD531/105352017-07-25 12:05:08.508oai:repositorio.ufsm.br:1/10535Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132017-07-25T15:05:08Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false
dc.title.por.fl_str_mv Bi-heterociclos a partir do Ácido Levulínico: Síntese de 5-[(5-(trifluormetil)-5-hidroxi-(3-substituido)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetil)pirazolo[1,5-a]pirimidinas
dc.title.alternative.eng.fl_str_mv From Levulinic Acid to Biheterocycles: Synthesis of 5-[(5-(trifluoromethyl)-5-hydroxy-(3-substituted)-4,5-dihydro-1H-pyrazol-1-yl)-1-propan-1-one-3-yl]-2-methyl-7-trifluoromethyl)pyrazolo [1,5-a]pyrimidines
title Bi-heterociclos a partir do Ácido Levulínico: Síntese de 5-[(5-(trifluormetil)-5-hidroxi-(3-substituido)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetil)pirazolo[1,5-a]pirimidinas
spellingShingle Bi-heterociclos a partir do Ácido Levulínico: Síntese de 5-[(5-(trifluormetil)-5-hidroxi-(3-substituido)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetil)pirazolo[1,5-a]pirimidinas
Rosales, Pauline Fagundes
Pirazolo[1,5-a]pirimidinas
Pirazóis
Bi-heterociclos
Pyrazolo[1,5-a]pyrimidines
Pyrazoles
Bi-heterocyclic
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Bi-heterociclos a partir do Ácido Levulínico: Síntese de 5-[(5-(trifluormetil)-5-hidroxi-(3-substituido)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetil)pirazolo[1,5-a]pirimidinas
title_full Bi-heterociclos a partir do Ácido Levulínico: Síntese de 5-[(5-(trifluormetil)-5-hidroxi-(3-substituido)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetil)pirazolo[1,5-a]pirimidinas
title_fullStr Bi-heterociclos a partir do Ácido Levulínico: Síntese de 5-[(5-(trifluormetil)-5-hidroxi-(3-substituido)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetil)pirazolo[1,5-a]pirimidinas
title_full_unstemmed Bi-heterociclos a partir do Ácido Levulínico: Síntese de 5-[(5-(trifluormetil)-5-hidroxi-(3-substituido)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetil)pirazolo[1,5-a]pirimidinas
title_sort Bi-heterociclos a partir do Ácido Levulínico: Síntese de 5-[(5-(trifluormetil)-5-hidroxi-(3-substituido)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetil)pirazolo[1,5-a]pirimidinas
author Rosales, Pauline Fagundes
author_facet Rosales, Pauline Fagundes
author_role author
dc.contributor.advisor1.fl_str_mv Flores, Alex Fabiani Claro
dc.contributor.advisor1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0
dc.contributor.referee1.fl_str_mv Pereira, Claudio Martin Pereira de
dc.contributor.referee1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4769201U4
dc.contributor.referee2.fl_str_mv Rodrigues, Oscar Endrigo Dorneles
dc.contributor.referee2Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4763956Z6
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/1677974893141092
dc.contributor.author.fl_str_mv Rosales, Pauline Fagundes
contributor_str_mv Flores, Alex Fabiani Claro
Pereira, Claudio Martin Pereira de
Rodrigues, Oscar Endrigo Dorneles
dc.subject.por.fl_str_mv Pirazolo[1,5-a]pirimidinas
Pirazóis
Bi-heterociclos
topic Pirazolo[1,5-a]pirimidinas
Pirazóis
Bi-heterociclos
Pyrazolo[1,5-a]pyrimidines
Pyrazoles
Bi-heterocyclic
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv Pyrazolo[1,5-a]pyrimidines
Pyrazoles
Bi-heterocyclic
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description An efficient method to obtain 2-methyl-5-(methylpropanoate-3-yl)-7-trifluoromethylpyrazolo[1,5-a]pyrimidine 2 from the reaction of compound methyl 7,7,7-trifluoro-4-methoxy-6-oxo-heptenoate with 3-amino-5-methyl-1H-pyrazol. This compound 2 brought to reaction with hydrazine monohydrate to obtain 2-methyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine-5-propanehydrazine 3 and after were later brought to cyclocondensation reaction with a series of β-alkoxyvinyltrifluoromethyl ketones giving the series of news bi-heterocyclic 5-[(5-(trifluoromethyl)-5-hydroxy- (3-substituted)-4,5-dihydro-1H-pyrazol-1-yl)-1-propan-1-one-3-yl]-2-methyl-7-trifluoro methyl)pyrazolo[1,5-a]pyrimidines compounds 5a-l. Compound 2-methyl-5-(methylpropanoate-3-yl)-7-trifluoromethylpyrazolo[1,5-a]pyrimidine 2 brought to transesterification reaction and hydrolises reaction for obtaining the compounds 6 and 7. The structures of all synthesized compounds were confirmed by 1H, 13C, 19F NMR data, and two-dimensional NMR techniques like HETCOR and COLOC, mass spectrometry data.
publishDate 2013
dc.date.issued.fl_str_mv 2013-03-04
dc.date.accessioned.fl_str_mv 2014-02-10
dc.date.available.fl_str_mv 2014-02-10
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dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
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status_str publishedVersion
dc.identifier.citation.fl_str_mv ROSALES, Pauline Fagundes. From Levulinic Acid to Biheterocycles: Synthesis of 5-[(5-(trifluoromethyl)-5-hydroxy-(3-substituted)-4,5-dihydro-1H-pyrazol-1-yl)-1-propan-1-one-3-yl]-2-methyl-7-trifluoromethyl)pyrazolo [1,5-a]pyrimidines. 2013. 198 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013.
dc.identifier.uri.fl_str_mv http://repositorio.ufsm.br/handle/1/10535
identifier_str_mv ROSALES, Pauline Fagundes. From Levulinic Acid to Biheterocycles: Synthesis of 5-[(5-(trifluoromethyl)-5-hydroxy-(3-substituted)-4,5-dihydro-1H-pyrazol-1-yl)-1-propan-1-one-3-yl]-2-methyl-7-trifluoromethyl)pyrazolo [1,5-a]pyrimidines. 2013. 198 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013.
url http://repositorio.ufsm.br/handle/1/10535
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dc.publisher.none.fl_str_mv Universidade Federal de Santa Maria
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 BR
dc.publisher.department.fl_str_mv Química
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