Uso de energia microondas na síntese de enonas e de 4,5-diidropirazóis trialometil-substituídos
Ano de defesa: | 2007 |
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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: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/4165 |
Resumo: | The solvent-free microwave-assisted regiospecific synthesis of a series of 5-trihalomethyl-4,5-dihydro-1H-pyrazole (7 - 10) from the cyclocondensation of 1,1,1- trihalo-4-alkoxy-3-alken-2-ones (5 - 6),[ CX3COC(R)2=C(R)1OR, where X = Cl, F; R = Me, Et; R2 = H, Me and R1 = H, Me, Et, Pr, iso-Pr, Bu, iso-Bu, tert-Bu, iso - Pen, Ph, 4-Me-Ph, 4-MeO-Ph, 4-NO2-Ph, 4-Cl-Ph, 4-Br-Ph, 4-F-Ph, H, OEt,] with carboxymethyl hydrazine or pentafluorophenyl hydrazine is described. The reaction was performed in a 1:1.2 molar ratio of alken-2-ones and hydrazine, in a single reaction step, for 6-12 minutes, in good yields (70-98%). The advantages obtained by using microwave irradiation under solvent-free conditions, rather than a conventional method, were also demonstrated. The 4-alkoxy-1,1,1-trihalo-3-alken-2-ones (4-5) were obtained from the reaction of cloreto de trichloroacetyl cloride or trifluoroacetic anhydride with enol ethers or acetals in presence of pyridine, solvent free and microwave induced techniques. |
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2017-05-222017-05-222007-08-17BECK, Paulo Henrique. Use of microwave irradiation in the synthesis of Enones and 4,5-dihydro-1h-pyrazoles Trihalomethyl-substituted. 2007. 213 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007.http://repositorio.ufsm.br/handle/1/4165The solvent-free microwave-assisted regiospecific synthesis of a series of 5-trihalomethyl-4,5-dihydro-1H-pyrazole (7 - 10) from the cyclocondensation of 1,1,1- trihalo-4-alkoxy-3-alken-2-ones (5 - 6),[ CX3COC(R)2=C(R)1OR, where X = Cl, F; R = Me, Et; R2 = H, Me and R1 = H, Me, Et, Pr, iso-Pr, Bu, iso-Bu, tert-Bu, iso - Pen, Ph, 4-Me-Ph, 4-MeO-Ph, 4-NO2-Ph, 4-Cl-Ph, 4-Br-Ph, 4-F-Ph, H, OEt,] with carboxymethyl hydrazine or pentafluorophenyl hydrazine is described. The reaction was performed in a 1:1.2 molar ratio of alken-2-ones and hydrazine, in a single reaction step, for 6-12 minutes, in good yields (70-98%). The advantages obtained by using microwave irradiation under solvent-free conditions, rather than a conventional method, were also demonstrated. The 4-alkoxy-1,1,1-trihalo-3-alken-2-ones (4-5) were obtained from the reaction of cloreto de trichloroacetyl cloride or trifluoroacetic anhydride with enol ethers or acetals in presence of pyridine, solvent free and microwave induced techniques.Este trabalho descreve a sintese rgeioespecifica de uma serie de 4,5-diidro-1Hpirazóis (7 - 10), por ciclocondensação de 4-alcóxi-1,1,1-trialo-3-alquen-2-onas, [ CX3COC(R)2=C(R)1OR, com X = Cl, F; R = Me, Et; R2 = H, Me; R1 = H, Me, Et, Pr, i-Pr, c-Pr, Bu, i-Bu, t-Bu, i-Pen, Pen, Ph, 4-Me-Ph, 4-MeO-Ph, 4-NO2-Ph, 4-Cl-Ph, 4-Br-Ph, 4-F-Ph, H, OEt] com carboximetil ou pentafluorfenil hidrazinas. As condições reacionais utilizadas para a síntese dos 4,5-diidropirazóis envolveu técnicas ambientalmente corretas, em um único passo e na ausência de solvente, usando 1:1.2 de relação molar das β-alcoxivinil cetonas e hidrazinas, em um único passo com um tempo de 6-12 minutos, com bons rendimentos (70-98%). Foram demonstradas as vantagens da condição, sem solvente e com uso de irradiação de microondas sobre o metodo convencional. A sintese das 4-alcóxi-1,1,1-trialo-3- alquen-2-onas (5 - 6) foram obtidas por reações de cloreto de tricloro acetila ou anidrido trifluoracetico com enoleteres ou acetais na presensa de piridina, livre de sonvente e tecnicas induzidas por microondas.Conselho Nacional de Desenvolvimento Científico e Tecnológicoapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaAcilaçãoEnonasPirazóisEnergia de microondasSem o uso de solventeAcylationEnonesPirazolesMicrowave irradiationSolvent-freeCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAUso de energia microondas na síntese de enonas e de 4,5-diidropirazóis trialometil-substituídosUse of microwave irradiation in the synthesis of Enones and 4,5-dihydro-1h-pyrazoles Trihalomethyl-substitutedinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisMartins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642Zanatta, Nilohttp://lattes.cnpq.br/0719465062354576Bonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Freitag, Rogério Antoniohttp://lattes.cnpq.br/3326079765076830http://lattes.cnpq.br/4175014494565472Beck, Paulo Henrique100600000000400300300300300300c28419d9-6027-4f9c-acd2-76e8067a85d10cd25fcc-995a-4530-b869-efd6954482c612036c3b-18f6-4b7d-ad7e-5fd56bfce1d76112c8ea-0206-4324-bf67-465ff831088f39b482b9-3e24-4a92-a99f-b554a3f84814info:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALPAULOHENRIQUEBECK.pdfapplication/pdf3034978http://repositorio.ufsm.br/bitstream/1/4165/1/PAULOHENRIQUEBECK.pdf9716625c1dc3d40e7c771e3349f09930MD51TEXTPAULOHENRIQUEBECK.pdf.txtPAULOHENRIQUEBECK.pdf.txtExtracted texttext/plain197563http://repositorio.ufsm.br/bitstream/1/4165/2/PAULOHENRIQUEBECK.pdf.txt2cfd005b725ddaee31a6aa6b3b943fc1MD52THUMBNAILPAULOHENRIQUEBECK.pdf.jpgPAULOHENRIQUEBECK.pdf.jpgIM Thumbnailimage/jpeg5920http://repositorio.ufsm.br/bitstream/1/4165/3/PAULOHENRIQUEBECK.pdf.jpgd3b32aa23d65ae8f17852386aba1584dMD531/41652023-01-02 11:55:16.644oai:repositorio.ufsm.br:1/4165Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132023-01-02T14:55:16Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Uso de energia microondas na síntese de enonas e de 4,5-diidropirazóis trialometil-substituídos |
dc.title.alternative.eng.fl_str_mv |
Use of microwave irradiation in the synthesis of Enones and 4,5-dihydro-1h-pyrazoles Trihalomethyl-substituted |
title |
Uso de energia microondas na síntese de enonas e de 4,5-diidropirazóis trialometil-substituídos |
spellingShingle |
Uso de energia microondas na síntese de enonas e de 4,5-diidropirazóis trialometil-substituídos Beck, Paulo Henrique Acilação Enonas Pirazóis Energia de microondas Sem o uso de solvente Acylation Enones Pirazoles Microwave irradiation Solvent-free CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Uso de energia microondas na síntese de enonas e de 4,5-diidropirazóis trialometil-substituídos |
title_full |
Uso de energia microondas na síntese de enonas e de 4,5-diidropirazóis trialometil-substituídos |
title_fullStr |
Uso de energia microondas na síntese de enonas e de 4,5-diidropirazóis trialometil-substituídos |
title_full_unstemmed |
Uso de energia microondas na síntese de enonas e de 4,5-diidropirazóis trialometil-substituídos |
title_sort |
Uso de energia microondas na síntese de enonas e de 4,5-diidropirazóis trialometil-substituídos |
author |
Beck, Paulo Henrique |
author_facet |
Beck, Paulo Henrique |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/6457412713967642 |
dc.contributor.referee1.fl_str_mv |
Zanatta, Nilo |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.referee2.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
dc.contributor.referee3.fl_str_mv |
Freitag, Rogério Antonio |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/3326079765076830 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/4175014494565472 |
dc.contributor.author.fl_str_mv |
Beck, Paulo Henrique |
contributor_str_mv |
Martins, Marcos Antonio Pinto Zanatta, Nilo Bonacorso, Helio Gauze Freitag, Rogério Antonio |
dc.subject.por.fl_str_mv |
Acilação Enonas Pirazóis Energia de microondas Sem o uso de solvente |
topic |
Acilação Enonas Pirazóis Energia de microondas Sem o uso de solvente Acylation Enones Pirazoles Microwave irradiation Solvent-free CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Acylation Enones Pirazoles Microwave irradiation Solvent-free |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The solvent-free microwave-assisted regiospecific synthesis of a series of 5-trihalomethyl-4,5-dihydro-1H-pyrazole (7 - 10) from the cyclocondensation of 1,1,1- trihalo-4-alkoxy-3-alken-2-ones (5 - 6),[ CX3COC(R)2=C(R)1OR, where X = Cl, F; R = Me, Et; R2 = H, Me and R1 = H, Me, Et, Pr, iso-Pr, Bu, iso-Bu, tert-Bu, iso - Pen, Ph, 4-Me-Ph, 4-MeO-Ph, 4-NO2-Ph, 4-Cl-Ph, 4-Br-Ph, 4-F-Ph, H, OEt,] with carboxymethyl hydrazine or pentafluorophenyl hydrazine is described. The reaction was performed in a 1:1.2 molar ratio of alken-2-ones and hydrazine, in a single reaction step, for 6-12 minutes, in good yields (70-98%). The advantages obtained by using microwave irradiation under solvent-free conditions, rather than a conventional method, were also demonstrated. The 4-alkoxy-1,1,1-trihalo-3-alken-2-ones (4-5) were obtained from the reaction of cloreto de trichloroacetyl cloride or trifluoroacetic anhydride with enol ethers or acetals in presence of pyridine, solvent free and microwave induced techniques. |
publishDate |
2007 |
dc.date.issued.fl_str_mv |
2007-08-17 |
dc.date.accessioned.fl_str_mv |
2017-05-22 |
dc.date.available.fl_str_mv |
2017-05-22 |
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 |
BECK, Paulo Henrique. Use of microwave irradiation in the synthesis of Enones and 4,5-dihydro-1h-pyrazoles Trihalomethyl-substituted. 2007. 213 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/4165 |
identifier_str_mv |
BECK, Paulo Henrique. Use of microwave irradiation in the synthesis of Enones and 4,5-dihydro-1h-pyrazoles Trihalomethyl-substituted. 2007. 213 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007. |
url |
http://repositorio.ufsm.br/handle/1/4165 |
dc.language.iso.fl_str_mv |
por |
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por |
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100600000000 |
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400 300 300 300 300 300 |
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Universidade Federal de Santa Maria |
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