Síntese de novos isoxazóis e pirazóis a partir de derivados 1,3-diíno indólicos
Autor(a) principal: | |
---|---|
Data de Publicação: | 2015 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/4269 |
Resumo: | In this work it describe the synthesis and characterization of new 1,3-diynes indole derivatives, the 1,6-bis(1H-indol-1-yl)hexa-2,4-diynes (6 examples) and unsymmetrical 1-(5-arylpenta-2,4-diynyl)-1H-indoles (6 examples), which were obtained in yields between 60 and 85% by homo- and heterocoupling reactions from N-propargyl indolic precursors, derivative from 1H-indole, 5-methoxy-1H-indole, 5-bromo-1H-indole, 2-methyl-1H-indole, 5- (p-tolyl)-1H-indole and carbazole. Subsequently, methodologies were provided for the synthesis of novel isoxazoles (12 examples), 1H-pyrazoles (12 examples) and 1-aryl-1H-pyrazoles (14 examples) by hydroamination reaction between the previously synthesized 1,3-diynes and hydroxylamine, hydrazine and aryl hydrazines, respectively. This synthesis proved to be efficient and clean, since it is free from catalysts and using PEG 400 as the solvent. For each series of compounds, the synthesis was optimized and full the examples were characterized. All products were obtained with high selectivity and yields from 58 to 89% for isoxazoles, 68 to 96% for 1H-pyrazoles and 50 to 75% for the 1-aryl-1H-pyrazoles. |
id |
UFSM_626bfe3f9269bafbd4132e505828fbf1 |
---|---|
oai_identifier_str |
oai:repositorio.ufsm.br:1/4269 |
network_acronym_str |
UFSM |
network_name_str |
Manancial - Repositório Digital da UFSM |
repository_id_str |
|
spelling |
Síntese de novos isoxazóis e pirazóis a partir de derivados 1,3-diíno indólicosSynthesis of new isoxazoles and pyrazoles from 1,3-diyne-indole derivatesQuímicaPirazóisIsoxazoisCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAIn this work it describe the synthesis and characterization of new 1,3-diynes indole derivatives, the 1,6-bis(1H-indol-1-yl)hexa-2,4-diynes (6 examples) and unsymmetrical 1-(5-arylpenta-2,4-diynyl)-1H-indoles (6 examples), which were obtained in yields between 60 and 85% by homo- and heterocoupling reactions from N-propargyl indolic precursors, derivative from 1H-indole, 5-methoxy-1H-indole, 5-bromo-1H-indole, 2-methyl-1H-indole, 5- (p-tolyl)-1H-indole and carbazole. Subsequently, methodologies were provided for the synthesis of novel isoxazoles (12 examples), 1H-pyrazoles (12 examples) and 1-aryl-1H-pyrazoles (14 examples) by hydroamination reaction between the previously synthesized 1,3-diynes and hydroxylamine, hydrazine and aryl hydrazines, respectively. This synthesis proved to be efficient and clean, since it is free from catalysts and using PEG 400 as the solvent. For each series of compounds, the synthesis was optimized and full the examples were characterized. All products were obtained with high selectivity and yields from 58 to 89% for isoxazoles, 68 to 96% for 1H-pyrazoles and 50 to 75% for the 1-aryl-1H-pyrazoles.Este trabalho descreve, inicialmente, a síntese e a caracterização de novos compostos 1,3-diíno indólicos, os 1,6-bis(1H-indol-1-il)hexa-2,4-diínos simétricos (6 exemplos) e os 1-(5-arilpenta-2,4-diinil)-1H-indol não simétricos (6 exemplos), que foram obtidos com rendimentos entre 60 e 85%, após reações de homo- e heteroacoplamento com precursores indólicos N-propargílicos, derivados do 1H-indol, 5-metoxi-1H-indol, 5-bromo-1H-indol, 2-metil-1H-indol, 5-(p-toluil)-1H-indol e carbazol. Posteriormente, foram apresentadas metodologias para a síntese de novos isoxazóis (12 exemplos) e pirazóis 1H- (12 exemplos) e 1-aril-1H- (14 exemplos) através da reação de hidroaminação entre os diínos previamente sintetizados e hidroxilamina, hidrazina e aril hidrazinas, respectivamente. Esta síntese se mostrou eficiente e limpa, já que é livre de catalisadores e utiliza PEG 400 como solvente. Para cada série de compostos foi descrita a otimização, a preparação de uma variedade de exemplos e a caracterização completa. Todos os produtos foram obtidos com alta seletividade e em rendimentos entre 58 e 89% para os isoxazóis, entre 68 e 96% para os 1H-pirazóis e entre 50 e 75% para os 1-aril-1H-pirazóis.Universidade Federal de Santa MariaBRQuímicaUFSMPrograma de Pós-Graduação em QuímicaSilveira, Claudio da Cruzhttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4787782A3Merlo, Aloir Antoniohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4784263J5Appelt, Helmoz Roseniaimhttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4723562D2Bonacorso, Helio Gauzehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0Dornelles, Lucianohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797177P9Bassaco, Mariana Moro2017-05-192017-05-192015-04-06info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisapplication/pdfapplication/pdfBASSACO, Mariana Moro. Synthesis of new isoxazoles and pyrazoles from 1,3-diyne-indole derivates. 2015. 225 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2015.http://repositorio.ufsm.br/handle/1/4269porinfo:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSM2017-07-25T14:05:07Zoai:repositorio.ufsm.br:1/4269Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2017-07-25T14:05:07Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.none.fl_str_mv |
Síntese de novos isoxazóis e pirazóis a partir de derivados 1,3-diíno indólicos Synthesis of new isoxazoles and pyrazoles from 1,3-diyne-indole derivates |
title |
Síntese de novos isoxazóis e pirazóis a partir de derivados 1,3-diíno indólicos |
spellingShingle |
Síntese de novos isoxazóis e pirazóis a partir de derivados 1,3-diíno indólicos Bassaco, Mariana Moro Química Pirazóis Isoxazois CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de novos isoxazóis e pirazóis a partir de derivados 1,3-diíno indólicos |
title_full |
Síntese de novos isoxazóis e pirazóis a partir de derivados 1,3-diíno indólicos |
title_fullStr |
Síntese de novos isoxazóis e pirazóis a partir de derivados 1,3-diíno indólicos |
title_full_unstemmed |
Síntese de novos isoxazóis e pirazóis a partir de derivados 1,3-diíno indólicos |
title_sort |
Síntese de novos isoxazóis e pirazóis a partir de derivados 1,3-diíno indólicos |
author |
Bassaco, Mariana Moro |
author_facet |
Bassaco, Mariana Moro |
author_role |
author |
dc.contributor.none.fl_str_mv |
Silveira, Claudio da Cruz http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4787782A3 Merlo, Aloir Antonio http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4784263J5 Appelt, Helmoz Roseniaim http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4723562D2 Bonacorso, Helio Gauze http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0 Dornelles, Luciano http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797177P9 |
dc.contributor.author.fl_str_mv |
Bassaco, Mariana Moro |
dc.subject.por.fl_str_mv |
Química Pirazóis Isoxazois CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Química Pirazóis Isoxazois CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this work it describe the synthesis and characterization of new 1,3-diynes indole derivatives, the 1,6-bis(1H-indol-1-yl)hexa-2,4-diynes (6 examples) and unsymmetrical 1-(5-arylpenta-2,4-diynyl)-1H-indoles (6 examples), which were obtained in yields between 60 and 85% by homo- and heterocoupling reactions from N-propargyl indolic precursors, derivative from 1H-indole, 5-methoxy-1H-indole, 5-bromo-1H-indole, 2-methyl-1H-indole, 5- (p-tolyl)-1H-indole and carbazole. Subsequently, methodologies were provided for the synthesis of novel isoxazoles (12 examples), 1H-pyrazoles (12 examples) and 1-aryl-1H-pyrazoles (14 examples) by hydroamination reaction between the previously synthesized 1,3-diynes and hydroxylamine, hydrazine and aryl hydrazines, respectively. This synthesis proved to be efficient and clean, since it is free from catalysts and using PEG 400 as the solvent. For each series of compounds, the synthesis was optimized and full the examples were characterized. All products were obtained with high selectivity and yields from 58 to 89% for isoxazoles, 68 to 96% for 1H-pyrazoles and 50 to 75% for the 1-aryl-1H-pyrazoles. |
publishDate |
2015 |
dc.date.none.fl_str_mv |
2015-04-06 2017-05-19 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.uri.fl_str_mv |
BASSACO, Mariana Moro. Synthesis of new isoxazoles and pyrazoles from 1,3-diyne-indole derivates. 2015. 225 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2015. http://repositorio.ufsm.br/handle/1/4269 |
identifier_str_mv |
BASSACO, Mariana Moro. Synthesis of new isoxazoles and pyrazoles from 1,3-diyne-indole derivates. 2015. 225 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2015. |
url |
http://repositorio.ufsm.br/handle/1/4269 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria BR Química UFSM Programa de Pós-Graduação em Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria BR Química UFSM Programa de Pós-Graduação em Química |
dc.source.none.fl_str_mv |
reponame:Manancial - Repositório Digital da UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Manancial - Repositório Digital da UFSM |
collection |
Manancial - Repositório Digital da UFSM |
repository.name.fl_str_mv |
Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1805922081604370432 |