Síntese e reações de 5-trifluormetil- 4,5-diidro-1H-1-pirazoltiocarboxamida 3(4)-substituídos
Ano de defesa: | 2002 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
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: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/27118 |
Resumo: | This thesis describes the synthesis and application as bi-heterocyclic precursor a series of 3-aryl[alkyl]-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1- pyrazolethiocarboxamides (2), which are easily obtained from the direct cyclocondensation reaction of β-alkoxyvinyl trifluoromethyl ketones (1) with thiosemicarbazide in methanol, under mild conditions (r.t - 450C, 20-24 h) and in good yields (73-96%). Similarly, the 1H-1-pyrazolethiocarboxamide derivatives (2) were dehydrated and the thiocarboxamide group hydrolyzed in an one-step reaction by stirring with concentrated sulfuric acid under reflux for 4 hours to give the 3-aryl[alkyl]-5- trifluoromethyl-1H-pyrazoles (3) in good yield (57-75%). In a subsequent application reaction of 3-aryl[alkyl]-5-hydroxy-5-trifluoromethyl- 4,5-dihydro-1H-1-pyrazolethiocarboxamides (2), the synthesis of alkyl[aryl]-substituted 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-methylpyrazoles (4) in good yields (68- 90%) from a new ring transformation reaction of alkyl[aryl]-substituted-5-hydroxy-5- trifluoromethyl-4,5-dihydro-1H-1-pyrazolethiocarboxyamides (2) with methylhydrazine in THF (2-7 hours a 20-250C), is reported. The thermal dehydration reaction of these pyrazolines (4) furnished the respective N-methylpyrazoles (5). Finally, a convenient method for the synthesis of a novel series of eighteen noncondensed 5,5-bicycles, specifically 2-(3-alkyl(phenyl)-5-hydroxy-5-trifluoromethyl-4,5- dihydro-1H-pyrazol-1-yl)-4-phenyl-5-alkyl-thiazoles and -4,5,6,7- tetrahydrobenzothiazoles (6), in good yields (57-98%), from the reaction of 3-alkyl(phenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-pyrazolethiocarboxamide (2) with 2-bromoacetophenone, 2-bromopropiophenone and 2-bromocyclohexanone, is reported. The dehydration of these compounds by stirring at reflux for 5 hours with a mixture of concentrated sulfuric acid/acetic acid 1:10 v/v, led to the corresponding 2-[3- alky(phenyl)-5-trifluoromethyl-1H-pyrazol-1-yl]-4-phenyl-5-alkylthiazoles and respective -4,5,6,7-tetrahydrobenzothiazoles (7) in good yield (75-93%). |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2022-11-25T19:04:00Z2022-11-25T19:04:00Z2002-07-26http://repositorio.ufsm.br/handle/1/27118This thesis describes the synthesis and application as bi-heterocyclic precursor a series of 3-aryl[alkyl]-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1- pyrazolethiocarboxamides (2), which are easily obtained from the direct cyclocondensation reaction of β-alkoxyvinyl trifluoromethyl ketones (1) with thiosemicarbazide in methanol, under mild conditions (r.t - 450C, 20-24 h) and in good yields (73-96%). Similarly, the 1H-1-pyrazolethiocarboxamide derivatives (2) were dehydrated and the thiocarboxamide group hydrolyzed in an one-step reaction by stirring with concentrated sulfuric acid under reflux for 4 hours to give the 3-aryl[alkyl]-5- trifluoromethyl-1H-pyrazoles (3) in good yield (57-75%). In a subsequent application reaction of 3-aryl[alkyl]-5-hydroxy-5-trifluoromethyl- 4,5-dihydro-1H-1-pyrazolethiocarboxamides (2), the synthesis of alkyl[aryl]-substituted 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-methylpyrazoles (4) in good yields (68- 90%) from a new ring transformation reaction of alkyl[aryl]-substituted-5-hydroxy-5- trifluoromethyl-4,5-dihydro-1H-1-pyrazolethiocarboxyamides (2) with methylhydrazine in THF (2-7 hours a 20-250C), is reported. The thermal dehydration reaction of these pyrazolines (4) furnished the respective N-methylpyrazoles (5). Finally, a convenient method for the synthesis of a novel series of eighteen noncondensed 5,5-bicycles, specifically 2-(3-alkyl(phenyl)-5-hydroxy-5-trifluoromethyl-4,5- dihydro-1H-pyrazol-1-yl)-4-phenyl-5-alkyl-thiazoles and -4,5,6,7- tetrahydrobenzothiazoles (6), in good yields (57-98%), from the reaction of 3-alkyl(phenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-pyrazolethiocarboxamide (2) with 2-bromoacetophenone, 2-bromopropiophenone and 2-bromocyclohexanone, is reported. The dehydration of these compounds by stirring at reflux for 5 hours with a mixture of concentrated sulfuric acid/acetic acid 1:10 v/v, led to the corresponding 2-[3- alky(phenyl)-5-trifluoromethyl-1H-pyrazol-1-yl]-4-phenyl-5-alkylthiazoles and respective -4,5,6,7-tetrahydrobenzothiazoles (7) in good yield (75-93%).Nesta tese é descrita a síntese e derivatizações de uma série de 3-aril(alquil)-5- hidróxi-5-trifluormetil-4,5-diidro-1H-1-pirazoltiocarboxamidas (2), os quais são obtidos facilmente a partir da reação de ciclocondensação direta de β-alcoxivinil trifluormetil cetonas (1) com tiosemicarbazida em metanol, sob condições brandas (t.a – 450C, 20-24 h) e em bons rendimentos (73-96%). Compostos 2 quando submetidos as condições de desidratação em meio ácido sulfúrico concentrado sob refluxo por 4 horas, levaram à obtenção de 3-aril(alquil)-5-trifluormetil-1H-pirazóis (3), em bons rendimentos (57- 75%), através da hidrólise simultânea do grupo tiocarboxamida. Em reação subsequente, 3-aril(alquil)-5-hidróxi-5-trifluormetil-4,5-diidro-1H-1- pirazoltiocarboxamidas (2) forneceram 3-aril(alquil)-5-hidróxi-5-trifluormetil-4,5-diidro- 1H-1-metilpirazol substituídos (4), em bons rendimentos (68-90%), através de reação de transformação anelar. Estas transformações ocorreram à temperatura ambiente (20-250C), entre 2-7 horas, e utilizaram os compostos 2 e metil-hidrazina como reagentes. Posteriormente, os compostos 4 foram desidratados termicamente levando à síntese de Nmetilpirazóis respectivos (5). Finalmente, foi obtida uma nova série de dezoito 5,5-biciclos não-condensados, especificamente 2-[3-alquil(fenil)-5-hidróxi-5-trifluormetil-4,5-diidro-1H-pirazol-1-il]-4-fenil-5-alquil-tiazóis e -4,5,6,7-tetraidrobenzotiazóis (6), em bons rendimentos (57-98%), a partir da reação de 3-alquil(fenil)-5-hidróxi-5-trifluormetil-4,5-diidro-1H-1- pirazoltiocarboxamida (2) com 2-bromoacetofenona, 2-bromopropiofenona e 2- bromociclo-hexanona. Os compostos 6 quando submetidos à refluxo, por 5 horas, em uma mistura 1:10 v/v de ácido sulfúrico concentrado/ácido acético, originaram por desidratação os corespondentes 2-[3-alquil(fenil)-5-trifluormetil-1H-pirazol-1-il]-4-fenil- 5-alquiltiazóis e -4,5,6,7-tetraidrobenzotiazóis (7) em bons rendimentos (75-93%).Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESConselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade 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/openAccessCetonas trifluormetiladasPirazóis4,5-diidro-1H-pirazóisTrifluormetil pirazóisTiazóisPirazolil-tiazolCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e reações de 5-trifluormetil- 4,5-diidro-1H-1-pirazoltiocarboxamida 3(4)-substituídosSynthesis and reactions of 3(4)-substituted 5-trifluoromethyl- 4,5-dihydro-1H-1-pyrazolethiocarboxamideinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Andrade, Nubia BoechatNascimento, Maria da GraçaMartins, Marcos Antonio PintoZanatta, Nilohttp://lattes.cnpq.br/7381394178075740Wastowski, Arci Dirceu10060000000060060060060060060060006c852ad-d805-43c3-99d6-93a6a86f507cfd1bfb4c-e6bf-43cc-968b-c5ab5f70bdf09b297a30-3733-45d4-be49-5fe2c237e81c3031a20a-2040-42b6-aae2-39fe99b7f05461e3f21e-e99f-42f0-88a7-5efcc6352f94db72aa79-2ac0-4a18-90a9-823ea140938areponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUÍMICA_2002_WANTOWSKI_ARCI.pdfTES_PPGQUÍMICA_2002_WANTOWSKI_ARCI.pdfTese de Doutoradoapplication/pdf9858723http://repositorio.ufsm.br/bitstream/1/27118/1/TES_PPGQU%c3%8dMICA_2002_WANTOWSKI_ARCI.pdf82316a612cef42dc4b7981dddfaefcf7MD51LICENSElicense.txtlicense.txttext/plain; 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dc.title.por.fl_str_mv |
Síntese e reações de 5-trifluormetil- 4,5-diidro-1H-1-pirazoltiocarboxamida 3(4)-substituídos |
dc.title.alternative.eng.fl_str_mv |
Synthesis and reactions of 3(4)-substituted 5-trifluoromethyl- 4,5-dihydro-1H-1-pyrazolethiocarboxamide |
title |
Síntese e reações de 5-trifluormetil- 4,5-diidro-1H-1-pirazoltiocarboxamida 3(4)-substituídos |
spellingShingle |
Síntese e reações de 5-trifluormetil- 4,5-diidro-1H-1-pirazoltiocarboxamida 3(4)-substituídos Wastowski, Arci Dirceu Cetonas trifluormetiladas Pirazóis 4,5-diidro-1H-pirazóis Trifluormetil pirazóis Tiazóis Pirazolil-tiazol CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese e reações de 5-trifluormetil- 4,5-diidro-1H-1-pirazoltiocarboxamida 3(4)-substituídos |
title_full |
Síntese e reações de 5-trifluormetil- 4,5-diidro-1H-1-pirazoltiocarboxamida 3(4)-substituídos |
title_fullStr |
Síntese e reações de 5-trifluormetil- 4,5-diidro-1H-1-pirazoltiocarboxamida 3(4)-substituídos |
title_full_unstemmed |
Síntese e reações de 5-trifluormetil- 4,5-diidro-1H-1-pirazoltiocarboxamida 3(4)-substituídos |
title_sort |
Síntese e reações de 5-trifluormetil- 4,5-diidro-1H-1-pirazoltiocarboxamida 3(4)-substituídos |
author |
Wastowski, Arci Dirceu |
author_facet |
Wastowski, Arci Dirceu |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
dc.contributor.referee1.fl_str_mv |
Andrade, Nubia Boechat |
dc.contributor.referee2.fl_str_mv |
Nascimento, Maria da Graça |
dc.contributor.referee3.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.referee4.fl_str_mv |
Zanatta, Nilo |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/7381394178075740 |
dc.contributor.author.fl_str_mv |
Wastowski, Arci Dirceu |
contributor_str_mv |
Bonacorso, Helio Gauze Andrade, Nubia Boechat Nascimento, Maria da Graça Martins, Marcos Antonio Pinto Zanatta, Nilo |
dc.subject.por.fl_str_mv |
Cetonas trifluormetiladas Pirazóis 4,5-diidro-1H-pirazóis Trifluormetil pirazóis Tiazóis Pirazolil-tiazol |
topic |
Cetonas trifluormetiladas Pirazóis 4,5-diidro-1H-pirazóis Trifluormetil pirazóis Tiazóis Pirazolil-tiazol CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This thesis describes the synthesis and application as bi-heterocyclic precursor a series of 3-aryl[alkyl]-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1- pyrazolethiocarboxamides (2), which are easily obtained from the direct cyclocondensation reaction of β-alkoxyvinyl trifluoromethyl ketones (1) with thiosemicarbazide in methanol, under mild conditions (r.t - 450C, 20-24 h) and in good yields (73-96%). Similarly, the 1H-1-pyrazolethiocarboxamide derivatives (2) were dehydrated and the thiocarboxamide group hydrolyzed in an one-step reaction by stirring with concentrated sulfuric acid under reflux for 4 hours to give the 3-aryl[alkyl]-5- trifluoromethyl-1H-pyrazoles (3) in good yield (57-75%). In a subsequent application reaction of 3-aryl[alkyl]-5-hydroxy-5-trifluoromethyl- 4,5-dihydro-1H-1-pyrazolethiocarboxamides (2), the synthesis of alkyl[aryl]-substituted 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-methylpyrazoles (4) in good yields (68- 90%) from a new ring transformation reaction of alkyl[aryl]-substituted-5-hydroxy-5- trifluoromethyl-4,5-dihydro-1H-1-pyrazolethiocarboxyamides (2) with methylhydrazine in THF (2-7 hours a 20-250C), is reported. The thermal dehydration reaction of these pyrazolines (4) furnished the respective N-methylpyrazoles (5). Finally, a convenient method for the synthesis of a novel series of eighteen noncondensed 5,5-bicycles, specifically 2-(3-alkyl(phenyl)-5-hydroxy-5-trifluoromethyl-4,5- dihydro-1H-pyrazol-1-yl)-4-phenyl-5-alkyl-thiazoles and -4,5,6,7- tetrahydrobenzothiazoles (6), in good yields (57-98%), from the reaction of 3-alkyl(phenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-pyrazolethiocarboxamide (2) with 2-bromoacetophenone, 2-bromopropiophenone and 2-bromocyclohexanone, is reported. The dehydration of these compounds by stirring at reflux for 5 hours with a mixture of concentrated sulfuric acid/acetic acid 1:10 v/v, led to the corresponding 2-[3- alky(phenyl)-5-trifluoromethyl-1H-pyrazol-1-yl]-4-phenyl-5-alkylthiazoles and respective -4,5,6,7-tetrahydrobenzothiazoles (7) in good yield (75-93%). |
publishDate |
2002 |
dc.date.issued.fl_str_mv |
2002-07-26 |
dc.date.accessioned.fl_str_mv |
2022-11-25T19:04:00Z |
dc.date.available.fl_str_mv |
2022-11-25T19:04:00Z |
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 |
http://repositorio.ufsm.br/handle/1/27118 |
url |
http://repositorio.ufsm.br/handle/1/27118 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 600 |
dc.relation.authority.fl_str_mv |
06c852ad-d805-43c3-99d6-93a6a86f507c fd1bfb4c-e6bf-43cc-968b-c5ab5f70bdf0 9b297a30-3733-45d4-be49-5fe2c237e81c 3031a20a-2040-42b6-aae2-39fe99b7f054 61e3f21e-e99f-42f0-88a7-5efcc6352f94 db72aa79-2ac0-4a18-90a9-823ea140938a |
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: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/1/27118/1/TES_PPGQU%c3%8dMICA_2002_WANTOWSKI_ARCI.pdf http://repositorio.ufsm.br/bitstream/1/27118/3/license.txt http://repositorio.ufsm.br/bitstream/1/27118/2/license_rdf |
bitstream.checksum.fl_str_mv |
82316a612cef42dc4b7981dddfaefcf7 2f0571ecee68693bd5cd3f17c1e075df 4460e5956bc1d1639be9ae6146a50347 |
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 |
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1793240168067497984 |