Síntese de 2-trialoacetil-1-metoxicicloalquenos e sua aplicação na obtenção de cicloalcapirazóis e isoxazóis derivados
Ano de defesa: | 2008 |
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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: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/4179 |
Resumo: | This work describes the synthesis and characterization of 2-trihaloacetylmetoxycycloalkenes series derived from cyclical ketones (cyclohexanone, cycloheptanone, cyclooctanone and cyclododecanone). The 2-trihaloacetyl-1-metoxycycloalkenes were obtained from the reaction of trihaloacetylation of 1.1-dimetoxycycloalkanes. Eight 2-trihaloacetyl-1-metoxycycloalkenes have been synthesized, and four of these trichloroacetyl compounds are unprecedented in the literature. The 2-trifluoroacetyl-1-metoxycycloalkenes were employed in the regiospecific synthesis of 3-hydroxy-3-trifluoromethyl-cycloalka[c]isoxazole, 3-trifluoromethyl-cycloalka[c]isoxazole, 3-trifluoromethyl-cycloalka[c]1H-pyrazole, 2-acetyl-3-hydroxy-3-trifluoromethyl-cycloalka[c]1H-pyrazole, 2-carboxyamide-3-hydroxy-3-trifluoromethyl-cycloalka[c]1H-pyrazole, 4-(3-hydroxy-3-trifluoromethyl-cycloalka[c] pyrazole-2-yl]-7-chloroquinoline. The reactions of cyclocondensation employed 2-trifluoroacetyl-1- metoxycycloalkenes and five different 1,2-dinucleofiles (hydroxylamine, hydrazine hydrochloride, acetic hydrazine, semicarbazide and 4-hydrazine-7-chloroquinoline), leading to yield between 34-85%. All compounds were characterized by spectral and analytical experiments, 1H's and 13C's NMR, and its purity was demostrated by CG/MS and elemental analyses. |
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2017-05-192017-05-192008-08-06COSTA, Michelle Budke. Synthesis of 2-trihaloacetyl-1-metoxycycloalkenes and its application in obtaining cycloalca-pirazoles and isoxazoles derivaties. 2008. 195 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2008.http://repositorio.ufsm.br/handle/1/4179This work describes the synthesis and characterization of 2-trihaloacetylmetoxycycloalkenes series derived from cyclical ketones (cyclohexanone, cycloheptanone, cyclooctanone and cyclododecanone). The 2-trihaloacetyl-1-metoxycycloalkenes were obtained from the reaction of trihaloacetylation of 1.1-dimetoxycycloalkanes. Eight 2-trihaloacetyl-1-metoxycycloalkenes have been synthesized, and four of these trichloroacetyl compounds are unprecedented in the literature. The 2-trifluoroacetyl-1-metoxycycloalkenes were employed in the regiospecific synthesis of 3-hydroxy-3-trifluoromethyl-cycloalka[c]isoxazole, 3-trifluoromethyl-cycloalka[c]isoxazole, 3-trifluoromethyl-cycloalka[c]1H-pyrazole, 2-acetyl-3-hydroxy-3-trifluoromethyl-cycloalka[c]1H-pyrazole, 2-carboxyamide-3-hydroxy-3-trifluoromethyl-cycloalka[c]1H-pyrazole, 4-(3-hydroxy-3-trifluoromethyl-cycloalka[c] pyrazole-2-yl]-7-chloroquinoline. The reactions of cyclocondensation employed 2-trifluoroacetyl-1- metoxycycloalkenes and five different 1,2-dinucleofiles (hydroxylamine, hydrazine hydrochloride, acetic hydrazine, semicarbazide and 4-hydrazine-7-chloroquinoline), leading to yield between 34-85%. All compounds were characterized by spectral and analytical experiments, 1H's and 13C's NMR, and its purity was demostrated by CG/MS and elemental analyses.Este trabalho descreve a síntese e caracterização de uma série de 2-trialoacetil-1-metoxicicloalquenos derivados de cetonas cíclicas (ciclopentanona, cicloexanona, cicloeptanona, ciclooctanona e ciclododecanona). Os 2-trialoacetil-1-metoxicicloalquenos foram sintetizados a partir da reação de trialoacetilação de 1,1-dimetoxicicloalcanos. Foram sintetizadas oito 2-trialoacetil-1-metoxicicloalquenos, sendo que quatro destes compostos tricloroacetilados são inéditos na literatura. Os 2-trifluoracetil-1-metoxicicloalquenos foram empregados na síntese regioespecífica de 3-hidróxi-3-trifluormetil-cicloalca[c]isoxazol, 3-trifluormetilcicloalca[ c]isoxazol, 3-trifluormetil-cicloalca[c]1H-pirazol, 2-acetil-3-hidróxi-3-trifluormetil-cicloalca[c]1H-pirazol, 2-carboxiamida-3-hidróxi-3-trifluormetilcicloalca[c]1H-pirazol, 4-{3-hidróxi-3-trifluormetil-cicloalca[c]pirazol-2-il]-7-cloroquinolina. As reações de ciclocondensação empregaram 2-trifluoracetil-1- metoxicicloalquenos e cinco diferentes 1,2-dinucleófilos, hidroxilamina, cloridrato de hidrazina, hidrazina acética, semicarbazida e 4-hidrazina-7-cloroquinolina, levando a rendimentos entre 34-85%. A análise estrutural de 2-trialoacetil-1-metoxicicloalquenos, bem como os cicloalca[c]azo compostos sintetizados foram caracterizados por experimentos de RMN de 1H, 13C, e sua pureza determinada via CGMS e análise elementar.Conselho Nacional de Desenvolvimento Científico e Tecnológicoapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaHeterociclosTrifluormetilCicloalcanonasTrialoacetilcicloalcanonasCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 2-trialoacetil-1-metoxicicloalquenos e sua aplicação na obtenção de cicloalcapirazóis e isoxazóis derivadosSynthesis of 2-trihaloacetyl-1-metoxycycloalkenes and its application in obtaining cycloalca-pirazoles and isoxazoles derivatiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Zanatta, Nilohttp://lattes.cnpq.br/0719465062354576Dalcol, Ionara Irionhttp://lattes.cnpq.br/9769548819312192Appelt, Helmoz Roseniaimhttp://lattes.cnpq.br/5360357766246970Obregon, Adriana Dornelles Carpeshttp://lattes.cnpq.br/9735757544227661http://lattes.cnpq.br/8752647892614261Costa, Michelle Budke10060000000040030030030030030030006c852ad-d805-43c3-99d6-93a6a86f507c3baf8e48-3c88-4e04-b0f1-16ff2053fdeb12036c3b-18f6-4b7d-ad7e-5fd56bfce1d7a40bb239-8ee1-458e-9d6a-c027ca35d1ff208c1834-aaa3-42a8-9b15-94470d8775e0e4bbaeee-3ded-43e8-a9d1-c28e6cbf73cdinfo:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALCOSTA, MICHELLE BUDKE.pdfapplication/pdf6046000http://repositorio.ufsm.br/bitstream/1/4179/1/COSTA%2c%20MICHELLE%20BUDKE.pdf8425bce4ea72c2d310120530b09e3c5cMD51TEXTCOSTA, MICHELLE BUDKE.pdf.txtCOSTA, MICHELLE BUDKE.pdf.txtExtracted texttext/plain203072http://repositorio.ufsm.br/bitstream/1/4179/2/COSTA%2c%20MICHELLE%20BUDKE.pdf.txtf476f75c10e4e587f203f89d1df4dc5eMD52THUMBNAILCOSTA, MICHELLE BUDKE.pdf.jpgCOSTA, MICHELLE BUDKE.pdf.jpgIM Thumbnailimage/jpeg5884http://repositorio.ufsm.br/bitstream/1/4179/3/COSTA%2c%20MICHELLE%20BUDKE.pdf.jpg80d3574162b09cf5529600a68b3cb27aMD531/41792023-04-19 13:45:44.514oai:repositorio.ufsm.br:1/4179Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2023-04-19T16:45:44Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de 2-trialoacetil-1-metoxicicloalquenos e sua aplicação na obtenção de cicloalcapirazóis e isoxazóis derivados |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 2-trihaloacetyl-1-metoxycycloalkenes and its application in obtaining cycloalca-pirazoles and isoxazoles derivaties |
title |
Síntese de 2-trialoacetil-1-metoxicicloalquenos e sua aplicação na obtenção de cicloalcapirazóis e isoxazóis derivados |
spellingShingle |
Síntese de 2-trialoacetil-1-metoxicicloalquenos e sua aplicação na obtenção de cicloalcapirazóis e isoxazóis derivados Costa, Michelle Budke Heterociclos Trifluormetil Cicloalcanonas Trialoacetilcicloalcanonas CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 2-trialoacetil-1-metoxicicloalquenos e sua aplicação na obtenção de cicloalcapirazóis e isoxazóis derivados |
title_full |
Síntese de 2-trialoacetil-1-metoxicicloalquenos e sua aplicação na obtenção de cicloalcapirazóis e isoxazóis derivados |
title_fullStr |
Síntese de 2-trialoacetil-1-metoxicicloalquenos e sua aplicação na obtenção de cicloalcapirazóis e isoxazóis derivados |
title_full_unstemmed |
Síntese de 2-trialoacetil-1-metoxicicloalquenos e sua aplicação na obtenção de cicloalcapirazóis e isoxazóis derivados |
title_sort |
Síntese de 2-trialoacetil-1-metoxicicloalquenos e sua aplicação na obtenção de cicloalcapirazóis e isoxazóis derivados |
author |
Costa, Michelle Budke |
author_facet |
Costa, Michelle Budke |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
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 |
Dalcol, Ionara Irion |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/9769548819312192 |
dc.contributor.referee3.fl_str_mv |
Appelt, Helmoz Roseniaim |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/5360357766246970 |
dc.contributor.referee4.fl_str_mv |
Obregon, Adriana Dornelles Carpes |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/9735757544227661 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/8752647892614261 |
dc.contributor.author.fl_str_mv |
Costa, Michelle Budke |
contributor_str_mv |
Bonacorso, Helio Gauze Zanatta, Nilo Dalcol, Ionara Irion Appelt, Helmoz Roseniaim Obregon, Adriana Dornelles Carpes |
dc.subject.por.fl_str_mv |
Heterociclos Trifluormetil Cicloalcanonas Trialoacetilcicloalcanonas |
topic |
Heterociclos Trifluormetil Cicloalcanonas Trialoacetilcicloalcanonas CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work describes the synthesis and characterization of 2-trihaloacetylmetoxycycloalkenes series derived from cyclical ketones (cyclohexanone, cycloheptanone, cyclooctanone and cyclododecanone). The 2-trihaloacetyl-1-metoxycycloalkenes were obtained from the reaction of trihaloacetylation of 1.1-dimetoxycycloalkanes. Eight 2-trihaloacetyl-1-metoxycycloalkenes have been synthesized, and four of these trichloroacetyl compounds are unprecedented in the literature. The 2-trifluoroacetyl-1-metoxycycloalkenes were employed in the regiospecific synthesis of 3-hydroxy-3-trifluoromethyl-cycloalka[c]isoxazole, 3-trifluoromethyl-cycloalka[c]isoxazole, 3-trifluoromethyl-cycloalka[c]1H-pyrazole, 2-acetyl-3-hydroxy-3-trifluoromethyl-cycloalka[c]1H-pyrazole, 2-carboxyamide-3-hydroxy-3-trifluoromethyl-cycloalka[c]1H-pyrazole, 4-(3-hydroxy-3-trifluoromethyl-cycloalka[c] pyrazole-2-yl]-7-chloroquinoline. The reactions of cyclocondensation employed 2-trifluoroacetyl-1- metoxycycloalkenes and five different 1,2-dinucleofiles (hydroxylamine, hydrazine hydrochloride, acetic hydrazine, semicarbazide and 4-hydrazine-7-chloroquinoline), leading to yield between 34-85%. All compounds were characterized by spectral and analytical experiments, 1H's and 13C's NMR, and its purity was demostrated by CG/MS and elemental analyses. |
publishDate |
2008 |
dc.date.issued.fl_str_mv |
2008-08-06 |
dc.date.accessioned.fl_str_mv |
2017-05-19 |
dc.date.available.fl_str_mv |
2017-05-19 |
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 |
COSTA, Michelle Budke. Synthesis of 2-trihaloacetyl-1-metoxycycloalkenes and its application in obtaining cycloalca-pirazoles and isoxazoles derivaties. 2008. 195 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2008. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/4179 |
identifier_str_mv |
COSTA, Michelle Budke. Synthesis of 2-trihaloacetyl-1-metoxycycloalkenes and its application in obtaining cycloalca-pirazoles and isoxazoles derivaties. 2008. 195 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2008. |
url |
http://repositorio.ufsm.br/handle/1/4179 |
dc.language.iso.fl_str_mv |
por |
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por |
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100600000000 |
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Universidade Federal de Santa Maria |
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Programa de Pós-Graduação em Química |
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UFSM |
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BR |
dc.publisher.department.fl_str_mv |
Química |
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Universidade Federal de Santa Maria |
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