Preparação de 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas como precursores para síntese de 3-trialometil-[3-carboxi] isoselenazóis

Detalhes bibliográficos
Ano de defesa: 2002
Autor(a) principal: Bastos, Giovani Palma lattes
Orientador(a): Martins, Marcos Antonio Pinto lattes
Banca de defesa: Grosmann, Grace, Freitag, Rogério Antônio, Zanatta, Nilo, Bonacorso, Hélio Gauze
Tipo de documento: Tese
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
Programa de Pós-Graduação: Programa de Pós-Graduação em Química
Departamento: Química
País: Brasil
Palavras-chave em Português:
Química
Sintese quimica
Compostos heterociclicos
Química orgânica
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/27090
Resumo: A convenient synthesis of 16 1,1,1-trihalo-4-methyl[phenyl]seleno-3-alken-2-ones [CX3C(O)CH=CR1SeR, where X = Cl, F; R = Me, Ph e R1 = H, Me, Et, n-Pr, iso-Pr, iso-Bu, Ph, 4-F-C6H4 e 4-Cl-C6H4], from the reaction of the corresponding 1,1,1-trihalo-4-methoxy-3-alken-2-ones with selenium nucleophilic in presence of boron trifluoride etherate, is reported. The reaction of the 1,1,1-trihalo-4-methyl[phenyl]seleno-3-alken-2-ones with bromine and ammonia to –700C furnished the of 3-trihalomethyl isoselenazoles in good yelds ( 68 – 81% ). The reaction of 3-trihalomethyl isoselenazoles in sulfuric acid and water as solvent, lead to the isoselenazoles carboxilic acids ( 70 – 80% ), while the reaction of the 3-trihalomethyl isoselenazoles in sulfuric acid and methanol as solvent lead to the respective methoxicarbonylselenazoles, in good yelds, ( 71 – 75% ), with the transformation of the CCl3 into CO2R2.
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spelling 2022-11-24T13:33:17Z2022-11-24T13:33:17Z2002-04-19http://repositorio.ufsm.br/handle/1/27090A convenient synthesis of 16 1,1,1-trihalo-4-methyl[phenyl]seleno-3-alken-2-ones [CX3C(O)CH=CR1SeR, where X = Cl, F; R = Me, Ph e R1 = H, Me, Et, n-Pr, iso-Pr, iso-Bu, Ph, 4-F-C6H4 e 4-Cl-C6H4], from the reaction of the corresponding 1,1,1-trihalo-4-methoxy-3-alken-2-ones with selenium nucleophilic in presence of boron trifluoride etherate, is reported. The reaction of the 1,1,1-trihalo-4-methyl[phenyl]seleno-3-alken-2-ones with bromine and ammonia to –700C furnished the of 3-trihalomethyl isoselenazoles in good yelds ( 68 – 81% ). The reaction of 3-trihalomethyl isoselenazoles in sulfuric acid and water as solvent, lead to the isoselenazoles carboxilic acids ( 70 – 80% ), while the reaction of the 3-trihalomethyl isoselenazoles in sulfuric acid and methanol as solvent lead to the respective methoxicarbonylselenazoles, in good yelds, ( 71 – 75% ), with the transformation of the CCl3 into CO2R2.Este trabalho apresenta a síntese de 16 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas [CX3C(O)CH=CR1SeR, onde X = Cl, F; R = Me, Ph e R1 = H, Me, Et, n-Pr, iso-Pr, iso-Bu, Ph, 4-F-C6H4 e 4-Cl-C6H4], a partir da reação da correspondente 1,1,1-trialo-4-alcoxi-3-alquen-2-onas com selênio nucleofílico em presença de trifluorboroeterato como ácido de Lewis. A 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas ao reagirem com bromo elementar e amônia gasosa a –70 0C forneceram os 3-trialometil isoselenazóis em bons rendimentos ( 68 – 81% ). A reação dos 3-trialometil isoselenazóis em meio ácido sulfúrico e água como solvente, levou aos respectivos ácidos carboxiselenazóis ( 70 – 80% ), enquanto a reação dos 3-trialometil isoselenazóis 5 em meio ácido sulfúrico e metanol como solvente levou aos respectivos 3-metoxicarbonilselenazóis, em bons rendimentos ( 71 –75% ), com a transformação do grupo CCl3 em CO2R2.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessQuímicaSintese quimicaCompostos heterociclicosQuímica orgânicaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAPreparação de 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas como precursores para síntese de 3-trialometil-[3-carboxi] isoselenazóisPreparation of 4-methyl[phenyl]seleno-1,1,1-trihalo-3-alken-2-ones as precursor for the synthesis of 3-trihalomethyl [3-carboxy] - isoselenazolesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisMartins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642Grosmann, GraceFreitag, Rogério AntônioZanatta, NiloBonacorso, Hélio Gauzehttp://lattes.cnpq.br/3315734411059233Bastos, Giovani Palma100600000000600600600600600600600c28419d9-6027-4f9c-acd2-76e8067a85d1b994175f-e20c-4c90-8467-18d7739477f62d903201-b068-4028-9ef8-e869f4582196a3934cb9-6684-47ba-a107-e1cc9fecdeb9a3caf96b-54e9-4f59-95af-1941d0bb008787682def-c17b-45e6-ba79-43a5332193dfreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv Preparação de 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas como precursores para síntese de 3-trialometil-[3-carboxi] isoselenazóis
dc.title.alternative.eng.fl_str_mv Preparation of 4-methyl[phenyl]seleno-1,1,1-trihalo-3-alken-2-ones as precursor for the synthesis of 3-trihalomethyl [3-carboxy] - isoselenazoles
title Preparação de 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas como precursores para síntese de 3-trialometil-[3-carboxi] isoselenazóis
spellingShingle Preparação de 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas como precursores para síntese de 3-trialometil-[3-carboxi] isoselenazóis
Bastos, Giovani Palma
Química
Sintese quimica
Compostos heterociclicos
Química orgânica
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Preparação de 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas como precursores para síntese de 3-trialometil-[3-carboxi] isoselenazóis
title_full Preparação de 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas como precursores para síntese de 3-trialometil-[3-carboxi] isoselenazóis
title_fullStr Preparação de 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas como precursores para síntese de 3-trialometil-[3-carboxi] isoselenazóis
title_full_unstemmed Preparação de 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas como precursores para síntese de 3-trialometil-[3-carboxi] isoselenazóis
title_sort Preparação de 1,1,1-trialo-4-metil[fenil]seleno-3-alquen-2-onas como precursores para síntese de 3-trialometil-[3-carboxi] isoselenazóis
author Bastos, Giovani Palma
author_facet Bastos, Giovani Palma
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 Grosmann, Grace
dc.contributor.referee2.fl_str_mv Freitag, Rogério Antônio
dc.contributor.referee3.fl_str_mv Zanatta, Nilo
dc.contributor.referee4.fl_str_mv Bonacorso, Hélio Gauze
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/3315734411059233
dc.contributor.author.fl_str_mv Bastos, Giovani Palma
contributor_str_mv Martins, Marcos Antonio Pinto
Grosmann, Grace
Freitag, Rogério Antônio
Zanatta, Nilo
Bonacorso, Hélio Gauze
dc.subject.por.fl_str_mv Química
Sintese quimica
Compostos heterociclicos
Química orgânica
topic Química
Sintese quimica
Compostos heterociclicos
Química orgânica
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description A convenient synthesis of 16 1,1,1-trihalo-4-methyl[phenyl]seleno-3-alken-2-ones [CX3C(O)CH=CR1SeR, where X = Cl, F; R = Me, Ph e R1 = H, Me, Et, n-Pr, iso-Pr, iso-Bu, Ph, 4-F-C6H4 e 4-Cl-C6H4], from the reaction of the corresponding 1,1,1-trihalo-4-methoxy-3-alken-2-ones with selenium nucleophilic in presence of boron trifluoride etherate, is reported. The reaction of the 1,1,1-trihalo-4-methyl[phenyl]seleno-3-alken-2-ones with bromine and ammonia to –700C furnished the of 3-trihalomethyl isoselenazoles in good yelds ( 68 – 81% ). The reaction of 3-trihalomethyl isoselenazoles in sulfuric acid and water as solvent, lead to the isoselenazoles carboxilic acids ( 70 – 80% ), while the reaction of the 3-trihalomethyl isoselenazoles in sulfuric acid and methanol as solvent lead to the respective methoxicarbonylselenazoles, in good yelds, ( 71 – 75% ), with the transformation of the CCl3 into CO2R2.
publishDate 2002
dc.date.issued.fl_str_mv 2002-04-19
dc.date.accessioned.fl_str_mv 2022-11-24T13:33:17Z
dc.date.available.fl_str_mv 2022-11-24T13:33:17Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.rights.driver.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
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 Brasil
dc.publisher.department.fl_str_mv Química
publisher.none.fl_str_mv Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
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