Síntese de 3-alcoxiacrilamidas a partir de tricloroacetil enol éteres
Ano de defesa: | 2012 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
|
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
BR
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/10518 |
Resumo: | This work reports a effective method for the preparation of a series of the new 3-alkoxy acrylamides of general formula R3HNC(O)CR1=CR2(OR), where R/ R1/ R2 = Et/H/H, Me/H/Me, -(CH2)2-/H, -(CH2)3-/H; R3 = Allyl, n-Pr, Bn, Phenetyl. However, the 3-alkoxy acrylamides where R/ R1/ R2 = Et/H/H/, Me/H/Me, R3 = Bn, have already been described in the literature. The 3-alkoxy acrylamides were obtained through three reaction steps. The first step, β-alkoxyvinyl trichloroacetyl ketones were synthesized through the acylation of enolethers using trichloroacetyl chloride as the acylating agent. In the second step, β-alkoxyvinyl trichloroacetyl ketones were converted to the corresponding β-alkoxyvinyl carboxylic acids from a basic hydrolysis using a 1 M sodium hydroxide solution. In the third step, β-alkoxyvinyl carboxylic acids were treated with thionyl chloride, using toluene as solvent, leading to the corresponding acyl chlorides intermediaries, which were not isolated. The acyl chlorides were reacted with primary amines such as allylamine, propylamine, benzylamine, and phenethylamine under basic catalysis of triethylamine, furnishing a new series of 3-alkoxy acrylamides in good yields of 48-90%. The 3-alkoxy acrylamides obtained in this study were identified by 1H and 13C Nuclear Magnetic Resonance spectroscopy, Mass spectroscopy and Elemental analysis. Keywords: 3-alkoxy acrylamides, β-alkoxyvinyl carboxylic acids, β-alkoxyvinyl trichloroacetyl ketones, acyl chlorides, amines |
id |
UFSM_173a7c41f2115c859e9cec1e618aa9c5 |
---|---|
oai_identifier_str |
oai:repositorio.ufsm.br:1/10518 |
network_acronym_str |
UFSM |
network_name_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
repository_id_str |
|
spelling |
2017-05-122017-05-122012-02-24MELLO, Débora Lombe de. Synthesis of 3-alkoxy acrylamides from trichloroacetil enol ethers. 2012. 125 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2012.http://repositorio.ufsm.br/handle/1/10518This work reports a effective method for the preparation of a series of the new 3-alkoxy acrylamides of general formula R3HNC(O)CR1=CR2(OR), where R/ R1/ R2 = Et/H/H, Me/H/Me, -(CH2)2-/H, -(CH2)3-/H; R3 = Allyl, n-Pr, Bn, Phenetyl. However, the 3-alkoxy acrylamides where R/ R1/ R2 = Et/H/H/, Me/H/Me, R3 = Bn, have already been described in the literature. The 3-alkoxy acrylamides were obtained through three reaction steps. The first step, β-alkoxyvinyl trichloroacetyl ketones were synthesized through the acylation of enolethers using trichloroacetyl chloride as the acylating agent. In the second step, β-alkoxyvinyl trichloroacetyl ketones were converted to the corresponding β-alkoxyvinyl carboxylic acids from a basic hydrolysis using a 1 M sodium hydroxide solution. In the third step, β-alkoxyvinyl carboxylic acids were treated with thionyl chloride, using toluene as solvent, leading to the corresponding acyl chlorides intermediaries, which were not isolated. The acyl chlorides were reacted with primary amines such as allylamine, propylamine, benzylamine, and phenethylamine under basic catalysis of triethylamine, furnishing a new series of 3-alkoxy acrylamides in good yields of 48-90%. The 3-alkoxy acrylamides obtained in this study were identified by 1H and 13C Nuclear Magnetic Resonance spectroscopy, Mass spectroscopy and Elemental analysis. Keywords: 3-alkoxy acrylamides, β-alkoxyvinyl carboxylic acids, β-alkoxyvinyl trichloroacetyl ketones, acyl chlorides, aminesEste trabalho apresenta um método eficiente para preparação de uma série inédita de 3-alcoxiacrilamidas de fórmula geral R3HNC(O)CR1=CR2(OR), onde R/ R1/R2 = Et/H/H, Me/H/Me, -(CH2)2-/H, -(CH2)3-/H; R3 = Alil, n-Pr, Bn, Fenetil. Sendo que as 3-alcoxiacrilamidas onde R/ R1/ R2 = Et/H/H, Me/H/Me, R3 = Bn, já foram descritas anteriormente na literatura. As 3-alcoxiacrilamidas foram obtidas através de três etapas reacionais, sendo que a primeira etapa constitui-se da acilação dos enol éteres, utilizando cloreto de tricloroacetila como agente acilante. Na segunda etapa as β-alcoxivinil tricloroacetil cetonas sintetizadas anteriormente, foram convertidas aos respectivos ácidos β-alcoxivinil carboxílicos a partir da hidrólise básica (utilizando solução de NaOH 1 M). Na terceira etapa, os ácidos β-alcoxivinil carboxílicos foram submetidos à reação com cloreto de tionila, utilizando tolueno como solvente, formando como intermediários os cloretos ácidos, os quais não foram isolados. Posteriormente, esses cloretos ácidos foram submetidos á reação de substituição nucleofílica, utilizando diferentes aminas alquílicas primárias (alilamina, propilamina, benzilamina, fenetilamina) como nucleófilo, sob catálise básica de trietilamina, promovendo assim, a síntese da série inédita das 3-alcoxiacrilamidas com bons rendimentos de 48-90%. As 3-alcoxiacrilamidas obtidas neste trabalho foram identificadas através de técnicas de Ressonância Magnética Nuclear de Hidrogênio, Ressonância Magnética Nuclear de Carbono-13, Espectrometria de Massas e Análise elementar.application/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímica3-alcoxiacrilamidasÁcidos β-alcoxivinil carboxílicosβ-alcoxivinil tricloroacetil cetonasCloretos ácidosAminas primárias alquílicas3-alkoxy acrylamidesβ-alkoxyvinyl carboxylic acidsβ-alkoxyvinyl trichloroacetyl ketonesAcyl chloridesAminesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 3-alcoxiacrilamidas a partir de tricloroacetil enol éteresSynthesis of 3-alkoxy acrylamides from trichloroacetil enol ethersinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Flores, Alex Fabiani Clarohttp://lattes.cnpq.br/1159954352174167Fantinel, Leonardohttp://lattes.cnpq.br/3934644027018397http://lattes.cnpq.br/0395675025653002Mello, Débora Lombe de100600000000400500300500500233dc1de-ab03-4f57-9b85-e40dc01a2d4f70386445-7f10-464a-be01-fc2355abd7f74d308e51-3866-4274-9e77-03644c9383df079f4612-cd36-4354-af6f-25f7736dccd2info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALMELLO, DEBORA LOMBE DE.pdfapplication/pdf4372333http://repositorio.ufsm.br/bitstream/1/10518/1/MELLO%2c%20DEBORA%20LOMBE%20DE.pdfcdabf27c076b067c6b562543a075756dMD51TEXTMELLO, DEBORA LOMBE DE.pdf.txtMELLO, DEBORA LOMBE DE.pdf.txtExtracted texttext/plain137193http://repositorio.ufsm.br/bitstream/1/10518/2/MELLO%2c%20DEBORA%20LOMBE%20DE.pdf.txt87e8452097c02c3a2f77fffa30be7f3aMD52THUMBNAILMELLO, DEBORA LOMBE DE.pdf.jpgMELLO, DEBORA LOMBE DE.pdf.jpgIM Thumbnailimage/jpeg5733http://repositorio.ufsm.br/bitstream/1/10518/3/MELLO%2c%20DEBORA%20LOMBE%20DE.pdf.jpg828e5e639fbfab6930bc82e1d8dd7200MD531/105182023-06-14 12:31:08.252oai:repositorio.ufsm.br:1/10518Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2023-06-14T15:31:08Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de 3-alcoxiacrilamidas a partir de tricloroacetil enol éteres |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 3-alkoxy acrylamides from trichloroacetil enol ethers |
title |
Síntese de 3-alcoxiacrilamidas a partir de tricloroacetil enol éteres |
spellingShingle |
Síntese de 3-alcoxiacrilamidas a partir de tricloroacetil enol éteres Mello, Débora Lombe de 3-alcoxiacrilamidas Ácidos β-alcoxivinil carboxílicos β-alcoxivinil tricloroacetil cetonas Cloretos ácidos Aminas primárias alquílicas 3-alkoxy acrylamides β-alkoxyvinyl carboxylic acids β-alkoxyvinyl trichloroacetyl ketones Acyl chlorides Amines CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 3-alcoxiacrilamidas a partir de tricloroacetil enol éteres |
title_full |
Síntese de 3-alcoxiacrilamidas a partir de tricloroacetil enol éteres |
title_fullStr |
Síntese de 3-alcoxiacrilamidas a partir de tricloroacetil enol éteres |
title_full_unstemmed |
Síntese de 3-alcoxiacrilamidas a partir de tricloroacetil enol éteres |
title_sort |
Síntese de 3-alcoxiacrilamidas a partir de tricloroacetil enol éteres |
author |
Mello, Débora Lombe de |
author_facet |
Mello, Débora Lombe de |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Zanatta, Nilo |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.referee1.fl_str_mv |
Flores, Alex Fabiani Claro |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/1159954352174167 |
dc.contributor.referee2.fl_str_mv |
Fantinel, Leonardo |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/3934644027018397 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0395675025653002 |
dc.contributor.author.fl_str_mv |
Mello, Débora Lombe de |
contributor_str_mv |
Zanatta, Nilo Flores, Alex Fabiani Claro Fantinel, Leonardo |
dc.subject.por.fl_str_mv |
3-alcoxiacrilamidas Ácidos β-alcoxivinil carboxílicos β-alcoxivinil tricloroacetil cetonas Cloretos ácidos Aminas primárias alquílicas |
topic |
3-alcoxiacrilamidas Ácidos β-alcoxivinil carboxílicos β-alcoxivinil tricloroacetil cetonas Cloretos ácidos Aminas primárias alquílicas 3-alkoxy acrylamides β-alkoxyvinyl carboxylic acids β-alkoxyvinyl trichloroacetyl ketones Acyl chlorides Amines CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
3-alkoxy acrylamides β-alkoxyvinyl carboxylic acids β-alkoxyvinyl trichloroacetyl ketones Acyl chlorides Amines |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work reports a effective method for the preparation of a series of the new 3-alkoxy acrylamides of general formula R3HNC(O)CR1=CR2(OR), where R/ R1/ R2 = Et/H/H, Me/H/Me, -(CH2)2-/H, -(CH2)3-/H; R3 = Allyl, n-Pr, Bn, Phenetyl. However, the 3-alkoxy acrylamides where R/ R1/ R2 = Et/H/H/, Me/H/Me, R3 = Bn, have already been described in the literature. The 3-alkoxy acrylamides were obtained through three reaction steps. The first step, β-alkoxyvinyl trichloroacetyl ketones were synthesized through the acylation of enolethers using trichloroacetyl chloride as the acylating agent. In the second step, β-alkoxyvinyl trichloroacetyl ketones were converted to the corresponding β-alkoxyvinyl carboxylic acids from a basic hydrolysis using a 1 M sodium hydroxide solution. In the third step, β-alkoxyvinyl carboxylic acids were treated with thionyl chloride, using toluene as solvent, leading to the corresponding acyl chlorides intermediaries, which were not isolated. The acyl chlorides were reacted with primary amines such as allylamine, propylamine, benzylamine, and phenethylamine under basic catalysis of triethylamine, furnishing a new series of 3-alkoxy acrylamides in good yields of 48-90%. The 3-alkoxy acrylamides obtained in this study were identified by 1H and 13C Nuclear Magnetic Resonance spectroscopy, Mass spectroscopy and Elemental analysis. Keywords: 3-alkoxy acrylamides, β-alkoxyvinyl carboxylic acids, β-alkoxyvinyl trichloroacetyl ketones, acyl chlorides, amines |
publishDate |
2012 |
dc.date.issued.fl_str_mv |
2012-02-24 |
dc.date.accessioned.fl_str_mv |
2017-05-12 |
dc.date.available.fl_str_mv |
2017-05-12 |
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 |
MELLO, Débora Lombe de. Synthesis of 3-alkoxy acrylamides from trichloroacetil enol ethers. 2012. 125 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2012. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10518 |
identifier_str_mv |
MELLO, Débora Lombe de. Synthesis of 3-alkoxy acrylamides from trichloroacetil enol ethers. 2012. 125 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2012. |
url |
http://repositorio.ufsm.br/handle/1/10518 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
400 500 300 500 500 |
dc.relation.authority.fl_str_mv |
233dc1de-ab03-4f57-9b85-e40dc01a2d4f 70386445-7f10-464a-be01-fc2355abd7f7 4d308e51-3866-4274-9e77-03644c9383df 079f4612-cd36-4354-af6f-25f7736dccd2 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria |
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 |
BR |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações do 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 |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
bitstream.url.fl_str_mv |
http://repositorio.ufsm.br/bitstream/1/10518/1/MELLO%2c%20DEBORA%20LOMBE%20DE.pdf http://repositorio.ufsm.br/bitstream/1/10518/2/MELLO%2c%20DEBORA%20LOMBE%20DE.pdf.txt http://repositorio.ufsm.br/bitstream/1/10518/3/MELLO%2c%20DEBORA%20LOMBE%20DE.pdf.jpg |
bitstream.checksum.fl_str_mv |
cdabf27c076b067c6b562543a075756d 87e8452097c02c3a2f77fffa30be7f3a 828e5e639fbfab6930bc82e1d8dd7200 |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1793239988327940096 |