Estudo comparativo de métodos de oxidação de álcoois utilizando energia de microondas e reações sob suporte sólido

Detalhes bibliográficos
Ano de defesa: 2006
Autor(a) principal: Uliana, Marciana Pierina lattes
Orientador(a): Braibante, Mara Elisa Fortes lattes
Banca de defesa: Morel, Ademir Farias, Silva, Ubiratan Flores da, Dalcol, Ionara Irion
Tipo de documento: Dissertação
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:
Métodos de oxidação
K-10
Microondas
Heterociclos
Palavras-chave em Inglês:
Oxidation methods
Microwave irradiation
Heterocycles
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/23842
Resumo: In this work, a comparative study is presented of the oxidation of secondary alcohols to form ketones by different routes: (I) potassium permanganate adsorbed on copper sulfate as a solid support without solvent, (Ia) using microwave irradiation, or (Ib) using conventional heating; (II) potassium permanganate adsorbed on montmorillonite, K-10 at room temperature. The alcohols used in this study have structures based on alkyl chains (1a), cyclopentyl rings (1d), cyclohexyl rings with different substituents (1c, 1e, 1f, 1h), allylic alcohol (1f), benzylic alcohols (1g and 1i) and a hydroxyketone (1b). This structural diverse collection of alcohols was used to valid the oxidative protocols as a general method of oxidation. Since the principal line of research in our group is the formation of heterocyclic systems, we used benzil 2b, obtained from the oxidation of alcohol 1b, for the cyclization reaction with the 1,4 N- dinucleophiles such as semicarbazide hydrochloride and thiosemicarbazide to give the heterocycles 5,6-diphenyl-2,3-dihydro-1,2,4-triazin-3-one 4 and 5,6-diphenyl-2,3-dihydro- 1,2,4-triazin-3-thione 6, respectively. Different methodologies, reactions with microwave irradiation or in refluxing ethanol were also evaluated. The investigation of possible biological activity of the heterocyclic compounds 4 and 6 obtained was carried out using Bioautography method with different microorganisms.
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spelling 2022-03-22T19:06:22Z2022-03-22T19:06:22Z2006-09-01http://repositorio.ufsm.br/handle/1/23842In this work, a comparative study is presented of the oxidation of secondary alcohols to form ketones by different routes: (I) potassium permanganate adsorbed on copper sulfate as a solid support without solvent, (Ia) using microwave irradiation, or (Ib) using conventional heating; (II) potassium permanganate adsorbed on montmorillonite, K-10 at room temperature. The alcohols used in this study have structures based on alkyl chains (1a), cyclopentyl rings (1d), cyclohexyl rings with different substituents (1c, 1e, 1f, 1h), allylic alcohol (1f), benzylic alcohols (1g and 1i) and a hydroxyketone (1b). This structural diverse collection of alcohols was used to valid the oxidative protocols as a general method of oxidation. Since the principal line of research in our group is the formation of heterocyclic systems, we used benzil 2b, obtained from the oxidation of alcohol 1b, for the cyclization reaction with the 1,4 N- dinucleophiles such as semicarbazide hydrochloride and thiosemicarbazide to give the heterocycles 5,6-diphenyl-2,3-dihydro-1,2,4-triazin-3-one 4 and 5,6-diphenyl-2,3-dihydro- 1,2,4-triazin-3-thione 6, respectively. Different methodologies, reactions with microwave irradiation or in refluxing ethanol were also evaluated. The investigation of possible biological activity of the heterocyclic compounds 4 and 6 obtained was carried out using Bioautography method with different microorganisms.Nesse trabalho realizamos um estudo comparativo entre metodologias de oxidação visando a obtenção de cetonas pela oxidação de álcoois secundários, avaliando diferentes protocolos oxidativos; I. Permanganato de potássio adsorvido em sulfato de cobre como suporte sólido, sem solvente utilizando: (Ia) energia de microondas e (Ib) aquecimento convencional e II. Permanganato de potássio adsorvido em montmorillonita, K-10, a temperatura ambiente. Os álcoois empregados, possuem em sua estrutura, cadeias saturada aberta (1a), saturadas cíclicas com 5 membros (1d) e 6 membros e diferentes substituições (1c, 1e, 1f e 1h), álcool alílico (1f), benzílicos (1g e 1i) e a hidroxi cetona (1b). Esta diversidade estrutural dos álcoois foi utilizada no sentido de validar os protocolos oxidativos como método geral de oxidação. De acordo com a linha de pesquisa desenvolvida pelo nosso grupo de pesquisa, que visa a obtenção de sistemas heterocíclicos, neste trabalho, utilizamos a dicetona benzil 2b, obtida a partir da oxidação do álcool 1b para efetuarmos reação de ciclização com 1,4 N- dinucleófilos como; cloridrato de semicarbazida e a tiosemicarbazida obtendo-se os heterociclos 5,6-difenil-2,3-dihidro-1,2,4-triazin-3-ona 4 e 5,6-difenil-2,3-dihidro-1,2,4- triazin-3-tiona 6 avaliando também diferentes metodologias, reações com energia de microondas e reações com refluxo em etanol. A investigação da possível atividade biológica dos compostos heterocíclicos foi realizada através do método de bioautografia frente a diferentes microorganismos indicadores.porUniversidade 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/openAccessMétodos de oxidaçãoK-10MicroondasHeterociclosOxidation methodsMicrowave irradiationHeterocyclesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAEstudo comparativo de métodos de oxidação de álcoois utilizando energia de microondas e reações sob suporte sólidoComparative study of the methods of oxidation of alcohols using microwave energy and reactions with solid supportsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBraibante, Mara Elisa Forteshttp://lattes.cnpq.br/0685197822607977Morel, Ademir FariasSilva, Ubiratan Flores daDalcol, Ionara Irionhttp://lattes.cnpq.br/5189593236727694Uliana, Marciana Pierina1006000000006006006006006006006e9d3171-46d3-4ee5-a0a1-ee7cd026f24be3be1cf5-c4e1-4046-9cbe-9b7945f4187022df5f67-c304-4742-b982-4d1e6d30aecca0abbcc7-a5fe-4607-b353-f2083479920811b367fb-0eed-426e-9ab5-e42e52a8d098reponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUÍMICA_2006_ULIANA_MARCIANA.pdfDIS_PPGQUÍMICA_2006_ULIANA_MARCIANA.pdfDissertação de Mestradoapplication/pdf4775915http://repositorio.ufsm.br/bitstream/1/23842/1/DIS_PPGQU%c3%8dMICA_2006_ULIANA_MARCIANA.pdf2203dfb54cda761db75fd53552831b1dMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/23842/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/23842/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD531/238422022-03-22 16:06:23.057oai:repositorio.ufsm.br:1/23842TElDRU7Dh0EgREUgRElTVFJJQlVJw4fDg08gTsODTy1FWENMVVNJVkEKCkNvbSBhIGFwcmVzZW50YcOnw6NvIGRlc3RhIGxpY2Vuw6dhLCB2b2PDqiAobyBhdXRvciAoZXMpIG91IG8gdGl0dWxhciBkb3MgZGlyZWl0b3MgZGUgYXV0b3IpIGNvbmNlZGUgw6AgVW5pdmVyc2lkYWRlCkZlZGVyYWwgZGUgU2FudGEgTWFyaWEgKFVGU00pIG8gZGlyZWl0byBuw6NvLWV4Y2x1c2l2byBkZSByZXByb2R1emlyLCAgdHJhZHV6aXIgKGNvbmZvcm1lIGRlZmluaWRvIGFiYWl4byksIGUvb3UKZGlzdHJpYnVpciBhIHN1YSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gKGluY2x1aW5kbyBvIHJlc3VtbykgcG9yIHRvZG8gbyBtdW5kbyBubyBmb3JtYXRvIGltcHJlc3NvIGUgZWxldHLDtG5pY28gZQplbSBxdWFscXVlciBtZWlvLCBpbmNsdWluZG8gb3MgZm9ybWF0b3Mgw6F1ZGlvIG91IHbDrWRlby4KClZvY8OqIGNvbmNvcmRhIHF1ZSBhIFVGU00gcG9kZSwgc2VtIGFsdGVyYXIgbyBjb250ZcO6ZG8sIHRyYW5zcG9yIGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbwpwYXJhIHF1YWxxdWVyIG1laW8gb3UgZm9ybWF0byBwYXJhIGZpbnMgZGUgcHJlc2VydmHDp8Ojby4KClZvY8OqIHRhbWLDqW0gY29uY29yZGEgcXVlIGEgVUZTTSBwb2RlIG1hbnRlciBtYWlzIGRlIHVtYSBjw7NwaWEgYSBzdWEgdGVzZSBvdQpkaXNzZXJ0YcOnw6NvIHBhcmEgZmlucyBkZSBzZWd1cmFuw6dhLCBiYWNrLXVwIGUgcHJlc2VydmHDp8Ojby4KClZvY8OqIGRlY2xhcmEgcXVlIGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbyDDqSBvcmlnaW5hbCBlIHF1ZSB2b2PDqiB0ZW0gbyBwb2RlciBkZSBjb25jZWRlciBvcyBkaXJlaXRvcyBjb250aWRvcwpuZXN0YSBsaWNlbsOnYS4gVm9jw6ogdGFtYsOpbSBkZWNsYXJhIHF1ZSBvIGRlcMOzc2l0byBkYSBzdWEgdGVzZSBvdSBkaXNzZXJ0YcOnw6NvIG7Do28sIHF1ZSBzZWphIGRlIHNldQpjb25oZWNpbWVudG8sIGluZnJpbmdlIGRpcmVpdG9zIGF1dG9yYWlzIGRlIG5pbmd1w6ltLgoKQ2FzbyBhIHN1YSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gY29udGVuaGEgbWF0ZXJpYWwgcXVlIHZvY8OqIG7Do28gcG9zc3VpIGEgdGl0dWxhcmlkYWRlIGRvcyBkaXJlaXRvcyBhdXRvcmFpcywgdm9jw6oKZGVjbGFyYSBxdWUgb2J0ZXZlIGEgcGVybWlzc8OjbyBpcnJlc3RyaXRhIGRvIGRldGVudG9yIGRvcyBkaXJlaXRvcyBhdXRvcmFpcyBwYXJhIGNvbmNlZGVyIMOgIFVGU00Kb3MgZGlyZWl0b3MgYXByZXNlbnRhZG9zIG5lc3RhIGxpY2Vuw6dhLCBlIHF1ZSBlc3NlIG1hdGVyaWFsIGRlIHByb3ByaWVkYWRlIGRlIHRlcmNlaXJvcyBlc3TDoSBjbGFyYW1lbnRlCmlkZW50aWZpY2FkbyBlIHJlY29uaGVjaWRvIG5vIHRleHRvIG91IG5vIGNvbnRlw7pkbyBkYSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gb3JhIGRlcG9zaXRhZGEuCgpDQVNPIEEgVEVTRSBPVSBESVNTRVJUQcOHw4NPIE9SQSBERVBPU0lUQURBIFRFTkhBIFNJRE8gUkVTVUxUQURPIERFIFVNIFBBVFJPQ8ONTklPIE9VCkFQT0lPIERFIFVNQSBBR8OKTkNJQSBERSBGT01FTlRPIE9VIE9VVFJPIE9SR0FOSVNNTyBRVUUgTsODTyBTRUpBIEEgVUZTTQosIFZPQ8OKIERFQ0xBUkEgUVVFIFJFU1BFSVRPVSBUT0RPUyBFIFFVQUlTUVVFUiBESVJFSVRPUyBERSBSRVZJU8ODTyBDT01PClRBTULDiU0gQVMgREVNQUlTIE9CUklHQcOHw5VFUyBFWElHSURBUyBQT1IgQ09OVFJBVE8gT1UgQUNPUkRPLgoKQSBVRlNNIHNlIGNvbXByb21ldGUgYSBpZGVudGlmaWNhciBjbGFyYW1lbnRlIG8gc2V1IG5vbWUgKHMpIG91IG8ocykgbm9tZShzKSBkbyhzKQpkZXRlbnRvcihlcykgZG9zIGRpcmVpdG9zIGF1dG9yYWlzIGRhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbywgZSBuw6NvIGZhcsOhIHF1YWxxdWVyIGFsdGVyYcOnw6NvLCBhbMOpbSBkYXF1ZWxhcwpjb25jZWRpZGFzIHBvciBlc3RhIGxpY2Vuw6dhLgoKRepositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132022-03-22T19:06:23Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false
dc.title.por.fl_str_mv Estudo comparativo de métodos de oxidação de álcoois utilizando energia de microondas e reações sob suporte sólido
dc.title.alternative.eng.fl_str_mv Comparative study of the methods of oxidation of alcohols using microwave energy and reactions with solid supports
title Estudo comparativo de métodos de oxidação de álcoois utilizando energia de microondas e reações sob suporte sólido
spellingShingle Estudo comparativo de métodos de oxidação de álcoois utilizando energia de microondas e reações sob suporte sólido
Uliana, Marciana Pierina
Métodos de oxidação
K-10
Microondas
Heterociclos
Oxidation methods
Microwave irradiation
Heterocycles
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Estudo comparativo de métodos de oxidação de álcoois utilizando energia de microondas e reações sob suporte sólido
title_full Estudo comparativo de métodos de oxidação de álcoois utilizando energia de microondas e reações sob suporte sólido
title_fullStr Estudo comparativo de métodos de oxidação de álcoois utilizando energia de microondas e reações sob suporte sólido
title_full_unstemmed Estudo comparativo de métodos de oxidação de álcoois utilizando energia de microondas e reações sob suporte sólido
title_sort Estudo comparativo de métodos de oxidação de álcoois utilizando energia de microondas e reações sob suporte sólido
author Uliana, Marciana Pierina
author_facet Uliana, Marciana Pierina
author_role author
dc.contributor.advisor1.fl_str_mv Braibante, Mara Elisa Fortes
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/0685197822607977
dc.contributor.referee1.fl_str_mv Morel, Ademir Farias
dc.contributor.referee2.fl_str_mv Silva, Ubiratan Flores da
dc.contributor.referee3.fl_str_mv Dalcol, Ionara Irion
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/5189593236727694
dc.contributor.author.fl_str_mv Uliana, Marciana Pierina
contributor_str_mv Braibante, Mara Elisa Fortes
Morel, Ademir Farias
Silva, Ubiratan Flores da
Dalcol, Ionara Irion
dc.subject.por.fl_str_mv Métodos de oxidação
K-10
Microondas
Heterociclos
topic Métodos de oxidação
K-10
Microondas
Heterociclos
Oxidation methods
Microwave irradiation
Heterocycles
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv Oxidation methods
Microwave irradiation
Heterocycles
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description In this work, a comparative study is presented of the oxidation of secondary alcohols to form ketones by different routes: (I) potassium permanganate adsorbed on copper sulfate as a solid support without solvent, (Ia) using microwave irradiation, or (Ib) using conventional heating; (II) potassium permanganate adsorbed on montmorillonite, K-10 at room temperature. The alcohols used in this study have structures based on alkyl chains (1a), cyclopentyl rings (1d), cyclohexyl rings with different substituents (1c, 1e, 1f, 1h), allylic alcohol (1f), benzylic alcohols (1g and 1i) and a hydroxyketone (1b). This structural diverse collection of alcohols was used to valid the oxidative protocols as a general method of oxidation. Since the principal line of research in our group is the formation of heterocyclic systems, we used benzil 2b, obtained from the oxidation of alcohol 1b, for the cyclization reaction with the 1,4 N- dinucleophiles such as semicarbazide hydrochloride and thiosemicarbazide to give the heterocycles 5,6-diphenyl-2,3-dihydro-1,2,4-triazin-3-one 4 and 5,6-diphenyl-2,3-dihydro- 1,2,4-triazin-3-thione 6, respectively. Different methodologies, reactions with microwave irradiation or in refluxing ethanol were also evaluated. The investigation of possible biological activity of the heterocyclic compounds 4 and 6 obtained was carried out using Bioautography method with different microorganisms.
publishDate 2006
dc.date.issued.fl_str_mv 2006-09-01
dc.date.accessioned.fl_str_mv 2022-03-22T19:06:22Z
dc.date.available.fl_str_mv 2022-03-22T19:06:22Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://repositorio.ufsm.br/handle/1/23842
url http://repositorio.ufsm.br/handle/1/23842
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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
dc.source.none.fl_str_mv reponame:Manancial - Repositório Digital da UFSM
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