Sulfoximidovinil trifluormetil cetonas. Obtenção e aplicação na síntese de azóis e azinas derivadas
Autor(a) principal: | |
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Data de Publicação: | 2007 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional Manancial UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/10646 |
Resumo: | This work describes the synthesis of a new series of 4-alkyl(aryl)-4-tetramethylenesulfoximide-1,1,1-trifluorobut-3-en-2-ones (5a-k) by the O,N-exchange reactions of ketones (1a-k) [CF3C(O)CH=CR1R, where R = OMe, OEt; R1 = H, Me, Ph, 4-MePh, 4-MeOPh, 4-BrPh, 4-ClPh, 4-FPh, 4-NO2Ph, 4,4 -Bifenil, 1-Naftil] with tetramethylenesulfoximide (4) in absence of solvent and with 65-97% yields. Subsequently, the preparation of a new series of a geminated heterocyclic system 3-aryl-5-trifluorometyl-7,8-dihydro-6H-thieno[2,1-f] [1,2]-thiazine 1-oxide (6c-k) derivatives (60-85% yields) by an intramolecular cyclocondensation reactions of enones employing potassium t-butoxide in diethyl ether as solvent, is also reported. In a subsequent step, the O,N-exchange reactions of 4,4-diethoxy-1,1,1-trifluoro-3-buten-2-one (1l) with S,S-dimethylsulfoximide (2), S-methyl-S-phenylsulfoximide (3) e tetramethylenesulfoximide (4), to obtain the corresponding acyclic compounds 4-ethoxy-4-sulfoximide-1,1,1-trifluoro-3-buten-2-one (5l-m) are described. Also, the application of compound 4-ethoxy-4-dimethylsulfoximide-1,1,1-trifluoro-3-buten-2-one (5l) to obtain S,S-dimethylsulfoximide substituted pyrazoles, isoxazoles and pyrimidine (8-18), is reported. |
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2017-05-222017-05-222007-07-02VEZZOSI, Renata Pivetta. Sulfoximidovinyl trifluoromethyl ketones. Preparation and application in the synthesis of azoles and azines derivatives. 2007. 176 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007.http://repositorio.ufsm.br/handle/1/10646This work describes the synthesis of a new series of 4-alkyl(aryl)-4-tetramethylenesulfoximide-1,1,1-trifluorobut-3-en-2-ones (5a-k) by the O,N-exchange reactions of ketones (1a-k) [CF3C(O)CH=CR1R, where R = OMe, OEt; R1 = H, Me, Ph, 4-MePh, 4-MeOPh, 4-BrPh, 4-ClPh, 4-FPh, 4-NO2Ph, 4,4 -Bifenil, 1-Naftil] with tetramethylenesulfoximide (4) in absence of solvent and with 65-97% yields. Subsequently, the preparation of a new series of a geminated heterocyclic system 3-aryl-5-trifluorometyl-7,8-dihydro-6H-thieno[2,1-f] [1,2]-thiazine 1-oxide (6c-k) derivatives (60-85% yields) by an intramolecular cyclocondensation reactions of enones employing potassium t-butoxide in diethyl ether as solvent, is also reported. In a subsequent step, the O,N-exchange reactions of 4,4-diethoxy-1,1,1-trifluoro-3-buten-2-one (1l) with S,S-dimethylsulfoximide (2), S-methyl-S-phenylsulfoximide (3) e tetramethylenesulfoximide (4), to obtain the corresponding acyclic compounds 4-ethoxy-4-sulfoximide-1,1,1-trifluoro-3-buten-2-one (5l-m) are described. Also, the application of compound 4-ethoxy-4-dimethylsulfoximide-1,1,1-trifluoro-3-buten-2-one (5l) to obtain S,S-dimethylsulfoximide substituted pyrazoles, isoxazoles and pyrimidine (8-18), is reported.A presente dissertação descreve, inicialmente, a síntese de uma nova série de 4-alquil(aril)-4-tetrametilenosulfoximido-1,1,1-trifluor-3-buten-2-onas (5a-k) através da reação de substituição de b-alcoxivinil trifluormetil cetonas (1a-k) [CF3C(O)CH=CR1R, onde R = OMe, OEt; R1 = H, Me, Ph, 4-MePh, 4-MeOPh, 4-BrPh, 4-ClPh, 4-FPh, 4-NO2Ph,4,4 -Bifenil, 1-Naftil] com tetrametilenosulfoximida (4), na ausência de solvente, com rendimentos de 65-97%. Subseqüentemente, é descrita a síntese de uma nova série de heterociclos geminados 3-aril-5-trifluormetil-7,8-diidro-6H-tieno[2,1-f] [1,2]-tiazinas 1-óxido (6c-j), com 60-85% de rendimentos, obtidos a partir da reação de ciclização intramolecular das enonas, empregando t-butóxido de potássio em dietiléter. Numa etapa posterior, são descritas as reações de substituição de 4,4-dietoxi-1,1,1-trifluor-3-buten-2-ona (1l) com S,S-dimetilsulfoximida (2), S-metil-S-fenilsulfoximida (3) e tetrametilenosulfoximida (4), formando os intermediários acíclicos 4-etóxi-4-sulfoximido-1,1,1-trifluor-3-buten-2-ona (5l-m). Também, é descrita a aplicação do composto 4-etóxi-4-dimetilsulfoximido-1,1,1-trifluor-3-buten-2-ona (5l) na síntese de pirazóis, isoxazóis e pirimidina S,S-dimetilsulfoximido substituídos, (8-18).Conselho Nacional de Desenvolvimento Científico e Tecnológicoapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaQuímicaSíntese químicaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASulfoximidovinil trifluormetil cetonas. Obtenção e aplicação na síntese de azóis e azinas derivadasSulfoximidovinyl trifluoromethyl ketones. Preparation and application in the synthesis of azoles and azines derivativesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Rodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Martins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642http://lattes.cnpq.br/1954952387719626Vezzosi, Renata Pivetta10060000000040050030050050006c852ad-d805-43c3-99d6-93a6a86f507c9526754b-6f30-4580-94e8-f2677d6a217ed315e5ef-8c77-48c9-bc87-e90cab9c43e95450ad79-4703-4a15-93a4-86f80794d585info:eu-repo/semantics/openAccessreponame:Repositório Institucional Manancial UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALRENATA VEZZOSI.pdfapplication/pdf2075602http://repositorio.ufsm.br/bitstream/1/10646/1/RENATA%20VEZZOSI.pdf164f4d2e506e2aa110a75d13cacea83dMD511/106462023-03-06 08:37:24.006oai:repositorio.ufsm.br:1/10646Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestouvidoria@ufsm.bropendoar:39132023-03-06T11:37:24Repositório Institucional Manancial UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Sulfoximidovinil trifluormetil cetonas. Obtenção e aplicação na síntese de azóis e azinas derivadas |
dc.title.alternative.eng.fl_str_mv |
Sulfoximidovinyl trifluoromethyl ketones. Preparation and application in the synthesis of azoles and azines derivatives |
title |
Sulfoximidovinil trifluormetil cetonas. Obtenção e aplicação na síntese de azóis e azinas derivadas |
spellingShingle |
Sulfoximidovinil trifluormetil cetonas. Obtenção e aplicação na síntese de azóis e azinas derivadas Vezzosi, Renata Pivetta Química Síntese química CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Sulfoximidovinil trifluormetil cetonas. Obtenção e aplicação na síntese de azóis e azinas derivadas |
title_full |
Sulfoximidovinil trifluormetil cetonas. Obtenção e aplicação na síntese de azóis e azinas derivadas |
title_fullStr |
Sulfoximidovinil trifluormetil cetonas. Obtenção e aplicação na síntese de azóis e azinas derivadas |
title_full_unstemmed |
Sulfoximidovinil trifluormetil cetonas. Obtenção e aplicação na síntese de azóis e azinas derivadas |
title_sort |
Sulfoximidovinil trifluormetil cetonas. Obtenção e aplicação na síntese de azóis e azinas derivadas |
author |
Vezzosi, Renata Pivetta |
author_facet |
Vezzosi, Renata Pivetta |
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 |
Rodrigues, Oscar Endrigo Dorneles |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/6536519955416085 |
dc.contributor.referee2.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/6457412713967642 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/1954952387719626 |
dc.contributor.author.fl_str_mv |
Vezzosi, Renata Pivetta |
contributor_str_mv |
Bonacorso, Helio Gauze Rodrigues, Oscar Endrigo Dorneles Martins, Marcos Antonio Pinto |
dc.subject.por.fl_str_mv |
Química Síntese química |
topic |
Química Síntese química 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 of a new series of 4-alkyl(aryl)-4-tetramethylenesulfoximide-1,1,1-trifluorobut-3-en-2-ones (5a-k) by the O,N-exchange reactions of ketones (1a-k) [CF3C(O)CH=CR1R, where R = OMe, OEt; R1 = H, Me, Ph, 4-MePh, 4-MeOPh, 4-BrPh, 4-ClPh, 4-FPh, 4-NO2Ph, 4,4 -Bifenil, 1-Naftil] with tetramethylenesulfoximide (4) in absence of solvent and with 65-97% yields. Subsequently, the preparation of a new series of a geminated heterocyclic system 3-aryl-5-trifluorometyl-7,8-dihydro-6H-thieno[2,1-f] [1,2]-thiazine 1-oxide (6c-k) derivatives (60-85% yields) by an intramolecular cyclocondensation reactions of enones employing potassium t-butoxide in diethyl ether as solvent, is also reported. In a subsequent step, the O,N-exchange reactions of 4,4-diethoxy-1,1,1-trifluoro-3-buten-2-one (1l) with S,S-dimethylsulfoximide (2), S-methyl-S-phenylsulfoximide (3) e tetramethylenesulfoximide (4), to obtain the corresponding acyclic compounds 4-ethoxy-4-sulfoximide-1,1,1-trifluoro-3-buten-2-one (5l-m) are described. Also, the application of compound 4-ethoxy-4-dimethylsulfoximide-1,1,1-trifluoro-3-buten-2-one (5l) to obtain S,S-dimethylsulfoximide substituted pyrazoles, isoxazoles and pyrimidine (8-18), is reported. |
publishDate |
2007 |
dc.date.issued.fl_str_mv |
2007-07-02 |
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/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
VEZZOSI, Renata Pivetta. Sulfoximidovinyl trifluoromethyl ketones. Preparation and application in the synthesis of azoles and azines derivatives. 2007. 176 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10646 |
identifier_str_mv |
VEZZOSI, Renata Pivetta. Sulfoximidovinyl trifluoromethyl ketones. Preparation and application in the synthesis of azoles and azines derivatives. 2007. 176 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007. |
url |
http://repositorio.ufsm.br/handle/1/10646 |
dc.language.iso.fl_str_mv |
por |
language |
por |
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100600000000 |
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400 500 300 500 500 |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Universidade Federal de Santa Maria |
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Programa de Pós-Graduação em Química |
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UFSM |
dc.publisher.country.fl_str_mv |
BR |
dc.publisher.department.fl_str_mv |
Química |
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Universidade Federal de Santa Maria |
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