Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos
Autor(a) principal: | |
---|---|
Data de Publicação: | 2016 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFRPE |
Texto Completo: | http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7034 |
Resumo: | In this work, we synthesized novel 3,5-disubstituted 1,2,4-oxadiazoles. The synthetic strategy was developed via two routes, both using arylamidoximes and chloride 1-adamantanecarbonyl. The first route (Method A) was separated into two steps: in the step 1, the reaction was carried out at room temperature (30 oC), dichloromethane as solvent and inert argon atmosphere. O-Acylamidoxime intermediates were obtained in yields from 16 to 79%. In the step 2, O-acylamidoximes intermediates were subjected to focused microwave irradiation (FMWI) at 110 °C (power 150 W) for 5 min. 1,2,4-Oxadiazole derivatives were obtained in moderate to good yields of 56-84%. Another pathway (Method B), one-pot strategy applying focused microwave irradiation (110 oC, power 150 W, for 5 min) was developed to preparing 1,2,4-oxadiazoles from arylamidoximes and chloride 1-adamantanecarbonyl using DMF as solvent. However, the 1,2,4-oxadiazole derivatives were obtained with low (18%) and good (70%) yields in two cases. Attempts to synthesis of 1,2,4-oxadiazoles from the reaction between ethyl propiolate and arylamidoximes have not been success; however, only O-vinyl derivatives have been prepared. |
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OLIVEIRA, Ronaldo Nascimento deARAÚJO, Patrícia Lopes Barros deARAÚJO, Elmo Silvano deCAMARA, Celso de Amorimhttp://lattes.cnpq.br/4380324461311613AGUIAR, Deivson Ferreira2017-07-31T14:30:08Z2016-08-10AGUIAR, Deivson Ferreira. Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos. 2016. 131 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural de Pernambuco, Recife.http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7034In this work, we synthesized novel 3,5-disubstituted 1,2,4-oxadiazoles. The synthetic strategy was developed via two routes, both using arylamidoximes and chloride 1-adamantanecarbonyl. The first route (Method A) was separated into two steps: in the step 1, the reaction was carried out at room temperature (30 oC), dichloromethane as solvent and inert argon atmosphere. O-Acylamidoxime intermediates were obtained in yields from 16 to 79%. In the step 2, O-acylamidoximes intermediates were subjected to focused microwave irradiation (FMWI) at 110 °C (power 150 W) for 5 min. 1,2,4-Oxadiazole derivatives were obtained in moderate to good yields of 56-84%. Another pathway (Method B), one-pot strategy applying focused microwave irradiation (110 oC, power 150 W, for 5 min) was developed to preparing 1,2,4-oxadiazoles from arylamidoximes and chloride 1-adamantanecarbonyl using DMF as solvent. However, the 1,2,4-oxadiazole derivatives were obtained with low (18%) and good (70%) yields in two cases. Attempts to synthesis of 1,2,4-oxadiazoles from the reaction between ethyl propiolate and arylamidoximes have not been success; however, only O-vinyl derivatives have been prepared.Neste trabalho foram realizados sintetizados novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos. A estratégia sintética foi desenvolvida via duas rotas, ambas utilizando as arilamidoximas e o cloreto de 1-adamantanocarbonila. A primeira rota (método A) foi dividida em duas etapas: na etapa 1, a reação foi realizada em temperatura ambiente (30 °C), diclorometano e atmosfera inerte de argônio. Foram obtidos os intermediários O-acilamidoximas com rendimentos de 16-79%. Na etapa 2, os intermediários O-acil foram submetidos a irradiação de micro-ondas à temperatura de 110 °C (potência 150 W) durante 5 minutos. Os derivados 1,2,4-oxadiazólicos foram sintetizados em rendimentos de 56-84%. Na segunda rota (método B), aplicamos uma estratégia “one pot” sob irradiação de micro-ondas à temperatura de 110 °C (potência 150 W) por 5 minutos, e solvente dimetilformamida (DMF). No entanto, os derivados de 1,2,4-oxadiazóis foram obtidos com baixo (18%) e bom (70%) rendimentos. A tentativa de sintetizar 1,2,4-oxadiazóis a partir da reação entre o propiolato de etila e as arilamidoximas não teve êxito; contudo, apenas os derivados O-vinílicos foram preparados.Submitted by Mario BC (mario@bc.ufrpe.br) on 2017-07-31T14:30:08Z No. of bitstreams: 1 Deivson Ferreira Aguiar.pdf: 2590455 bytes, checksum: fa129376a1b84e8d2284f0f8067016b4 (MD5)Made available in DSpace on 2017-07-31T14:30:08Z (GMT). No. of bitstreams: 1 Deivson Ferreira Aguiar.pdf: 2590455 bytes, checksum: fa129376a1b84e8d2284f0f8067016b4 (MD5) Previous issue date: 2016-08-10Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESConselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqapplication/pdfporUniversidade Federal Rural de PernambucoPrograma de Pós-Graduação em QuímicaUFRPEBrasilDepartamento de QuímicaOxadiazolArilamidoximasAdamantanoCIENCIAS EXATAS E DA TERRA::QUIMICAEstudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídosinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesis1435648362225100898600600600600600380641605545709103015717003253031171952075167498588264571-2555911436985713659info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFRPEinstname:Universidade Federal Rural de Pernambuco (UFRPE)instacron:UFRPELICENSElicense.txtlicense.txttext/plain; charset=utf-82165http://www.tede2.ufrpe.br:8080/tede2/bitstream/tede2/7034/1/license.txtbd3efa91386c1718a7f26a329fdcb468MD51ORIGINALDeivson Ferreira Aguiar.pdfDeivson Ferreira Aguiar.pdfapplication/pdf2590455http://www.tede2.ufrpe.br:8080/tede2/bitstream/tede2/7034/2/Deivson+Ferreira+Aguiar.pdffa129376a1b84e8d2284f0f8067016b4MD52tede2/70342018-06-19 11:40:36.931oai:tede2: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Biblioteca Digital de Teses e Dissertaçõeshttp://www.tede2.ufrpe.br:8080/tede/PUBhttp://www.tede2.ufrpe.br:8080/oai/requestbdtd@ufrpe.br ||bdtd@ufrpe.bropendoar:2024-05-28T12:35:07.230133Biblioteca Digital de Teses e Dissertações da UFRPE - Universidade Federal Rural de Pernambuco (UFRPE)false |
dc.title.por.fl_str_mv |
Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos |
title |
Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos |
spellingShingle |
Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos AGUIAR, Deivson Ferreira Oxadiazol Arilamidoximas Adamantano CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos |
title_full |
Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos |
title_fullStr |
Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos |
title_full_unstemmed |
Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos |
title_sort |
Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos |
author |
AGUIAR, Deivson Ferreira |
author_facet |
AGUIAR, Deivson Ferreira |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
OLIVEIRA, Ronaldo Nascimento de |
dc.contributor.advisor-co1.fl_str_mv |
ARAÚJO, Patrícia Lopes Barros de |
dc.contributor.referee1.fl_str_mv |
ARAÚJO, Elmo Silvano de |
dc.contributor.referee2.fl_str_mv |
CAMARA, Celso de Amorim |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/4380324461311613 |
dc.contributor.author.fl_str_mv |
AGUIAR, Deivson Ferreira |
contributor_str_mv |
OLIVEIRA, Ronaldo Nascimento de ARAÚJO, Patrícia Lopes Barros de ARAÚJO, Elmo Silvano de CAMARA, Celso de Amorim |
dc.subject.por.fl_str_mv |
Oxadiazol Arilamidoximas Adamantano |
topic |
Oxadiazol Arilamidoximas Adamantano CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this work, we synthesized novel 3,5-disubstituted 1,2,4-oxadiazoles. The synthetic strategy was developed via two routes, both using arylamidoximes and chloride 1-adamantanecarbonyl. The first route (Method A) was separated into two steps: in the step 1, the reaction was carried out at room temperature (30 oC), dichloromethane as solvent and inert argon atmosphere. O-Acylamidoxime intermediates were obtained in yields from 16 to 79%. In the step 2, O-acylamidoximes intermediates were subjected to focused microwave irradiation (FMWI) at 110 °C (power 150 W) for 5 min. 1,2,4-Oxadiazole derivatives were obtained in moderate to good yields of 56-84%. Another pathway (Method B), one-pot strategy applying focused microwave irradiation (110 oC, power 150 W, for 5 min) was developed to preparing 1,2,4-oxadiazoles from arylamidoximes and chloride 1-adamantanecarbonyl using DMF as solvent. However, the 1,2,4-oxadiazole derivatives were obtained with low (18%) and good (70%) yields in two cases. Attempts to synthesis of 1,2,4-oxadiazoles from the reaction between ethyl propiolate and arylamidoximes have not been success; however, only O-vinyl derivatives have been prepared. |
publishDate |
2016 |
dc.date.issued.fl_str_mv |
2016-08-10 |
dc.date.accessioned.fl_str_mv |
2017-07-31T14:30:08Z |
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 |
AGUIAR, Deivson Ferreira. Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos. 2016. 131 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural de Pernambuco, Recife. |
dc.identifier.uri.fl_str_mv |
http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7034 |
identifier_str_mv |
AGUIAR, Deivson Ferreira. Estudos visando a síntese de novos derivados 1,2,4-oxadiazólicos 3,5-dissubstituídos. 2016. 131 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural de Pernambuco, Recife. |
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http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7034 |
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openAccess |
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Universidade Federal Rural de Pernambuco |
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Programa de Pós-Graduação em Química |
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UFRPE |
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Departamento de Química |
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Universidade Federal Rural de Pernambuco |
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