Síntese e estereoquímica de isoxazóis espiro-tetracíclicos trifluormetil substituídos
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional Manancial UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/14045 |
Resumo: | The present dissertation initially describes methodologies for the synthesis of five 3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkan]-3-ols (7) in 65 – 84 % yields, where the spirocarbocyclic portion is constituted by: cyclopentane, cyclohexane, cycloheptane, 4-methyl-cyclohexane or 4-tert-butyl-cyclohexane. The isoxazolines 7 where synthesized through cyclocondensation [3+2] employing 2,2,2-trifluoro-1-(4-methoxyspiro[chromene-2,1'-cyclopentan]-3-yl)ethan-1-one (6) as the 1,3dieletrophile [CCC], and hydroxylamine chloridrate as the 1,2-dinucleophile [NO] in the presence of NaHCO3 in 65 – 84 % yields. The stereochemistry involved in the isoxazolines (7) synthesis was discussed and elucidated using 1H, 13C, 19F NMR, HMQC, HMBC e NOESY 2-D-NMR and single crystal X-ray diffraction. In sequence the 3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkan]-3-ols (7) were dehydrated aiming to furnish a novel series of five 3-(trifluoromethyl)spiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkanes] (8). The dehydration was successfully performed in benzene/thionyl chloride media in 76 – 95 % yields. In a next reaction step the isoxazolines (7) were derivativated with propargyl bromide through a NS2 reaction furnishing a novel heterocyclic series of five 3-(prop-2-yn-1-yloxy)-3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkanes] (10) in 71 – 84 % yields. Finally the isolated terminal alkynes were successfully employed in the construction of a series of five examples of 3-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkanes] (12), in 36 – 84% yields. The methylene-bi-heterocyclic series (12), composed exclusively of 1,4-dissubstituted 1,2,3-triazoles, was obtained through a regoiselective 1,3 dipolar cycloaddition (Click Chemistry) catalyzed by copper iodide using terminal alkynes (10) and benzil Azide (NNN fragment). |
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2018-08-13T12:38:00Z2018-08-13T12:38:00Z2017-02-23http://repositorio.ufsm.br/handle/1/14045The present dissertation initially describes methodologies for the synthesis of five 3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkan]-3-ols (7) in 65 – 84 % yields, where the spirocarbocyclic portion is constituted by: cyclopentane, cyclohexane, cycloheptane, 4-methyl-cyclohexane or 4-tert-butyl-cyclohexane. The isoxazolines 7 where synthesized through cyclocondensation [3+2] employing 2,2,2-trifluoro-1-(4-methoxyspiro[chromene-2,1'-cyclopentan]-3-yl)ethan-1-one (6) as the 1,3dieletrophile [CCC], and hydroxylamine chloridrate as the 1,2-dinucleophile [NO] in the presence of NaHCO3 in 65 – 84 % yields. The stereochemistry involved in the isoxazolines (7) synthesis was discussed and elucidated using 1H, 13C, 19F NMR, HMQC, HMBC e NOESY 2-D-NMR and single crystal X-ray diffraction. In sequence the 3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkan]-3-ols (7) were dehydrated aiming to furnish a novel series of five 3-(trifluoromethyl)spiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkanes] (8). The dehydration was successfully performed in benzene/thionyl chloride media in 76 – 95 % yields. In a next reaction step the isoxazolines (7) were derivativated with propargyl bromide through a NS2 reaction furnishing a novel heterocyclic series of five 3-(prop-2-yn-1-yloxy)-3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkanes] (10) in 71 – 84 % yields. Finally the isolated terminal alkynes were successfully employed in the construction of a series of five examples of 3-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkanes] (12), in 36 – 84% yields. The methylene-bi-heterocyclic series (12), composed exclusively of 1,4-dissubstituted 1,2,3-triazoles, was obtained through a regoiselective 1,3 dipolar cycloaddition (Click Chemistry) catalyzed by copper iodide using terminal alkynes (10) and benzil Azide (NNN fragment).A presente dissertação descreve inicialmente metodologias para a obtenção de uma série de cinco 3-(trifluormetil)-3,3a-di-hidroespiro[cromeno[4,3-c]isoxazol-4,1'-cicloalcan]-3-óis (7) com rendimentos de 65 – 84 %, onde a porção espirocarbocíclica é constituída por: ciclopentano, ciclohexano, cicloheptano, 4-metil-ciclohexano ou 4-terc-butil-ciclohexano. As isoxazolinas 7 foram sintetizadas a partir de reações de ciclocondensação do tipo [3+2], empregando 2,2,2-triflúor-1-(4-metóxi-espiro[cromeno-2,1'-cicloalcan]-3-il)etan-1-onas (6) como 1,3-dieletrófilos [CCC], e cloridrato de hidroxilamina como 1,2-dinucleófilo [NO] na presença de NaHCO3 65 – 84 %. A estereoquímica envolvida na síntese das isoxazolinas 7 foi discutida e elucidada utilizando técnicas de RMN 1H, 13C 19F, RMN 2-D HMQC, HMBC e NOESY, e difração de raios X em mono cristais. Em sequência, foram procedidas reações de desidratação de 3-(trifluormetil)-3,3a-di-hidroespiro[cromeno[4,3-c]isoxazol-4,1'-cicloalcan]-3-óis (7), visando a obtenção de uma série inédita formada por cinco 3-(trifluormetil)espiro[cromeno[4,3-c]isoxazol-4,1'-cicloalcanos] (8). A desidratação foi realizada com êxito em meio benzeno/cloreto de tionila e em rendimentos de 76 – 95 %. Em passo reacional posterior, as isoxazolinas 7 foram derivatizadas com brometo de propargila, por meio de uma reação de O-alquilação via SN2, à uma série heterocíclica inédita constituída de cinco 3-(prop-2-in-1-ilóxi)-3-(trifluormetil)-3,3a-di-hidroespiro[cromeno[4,3-c]isoxazol-4,1'-cicloalcanos] (10), em rendimentos de 71 – 84 %. Finalmente, os alcinos terminais isolados 10 foram utilizados com sucesso na construção e isolamento de uma nova série de cinco exemplares de 3-((1-benzil-1H-1,2,3-triazol-4-il)metóxi)-3-(trifluormetil)-3,3a-di-hidroespiro[cromeno [4,3-c]isoxazol-4,1'-cicloalcanos] (12), em rendimentos de 36 – 84 %. A série metileno bi-heterocíclica 12, com a formação exclusiva de 1,2,3-triazóis 1,4-dissubstituídos, foi obtida através de uma reação de cicloadição 1,3-dipolar regiosseletiva (tipo Click Chemistry) catalisada por iodeto de cobre entre os alcinos terminais 10 e benzil azida (fragmento NNN).Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade 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/openAccessQuímicaQuímica orgânicaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e estereoquímica de isoxazóis espiro-tetracíclicos trifluormetil substituídosSynthesis and stereochemistry of trifluoromethyl substituted spiro-tetracyclic isoxazolesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Iglesias, Bernardo Almeidahttp://lattes.cnpq.br/4402375533322977Costa, Michele Budkehttp://lattes.cnpq.br/8752647892614261http://lattes.cnpq.br/3038644206836878Ketzer, Alex10060000000060006c852ad-d805-43c3-99d6-93a6a86f507c38fdae02-7eea-49cd-8dbe-76818e7538b6483d6d0c-e419-454b-b413-1a51673258c322bf0e37-aef4-4ce5-9f48-021f88245b47reponame:Repositório Institucional Manancial UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2017_KETZER_ALEX.pdfDIS_PPGQUIMICA_2017_KETZER_ALEX.pdfDissertação de Mestradoapplication/pdf14579066http://repositorio.ufsm.br/bitstream/1/14045/1/DIS_PPGQUIMICA_2017_KETZER_ALEX.pdf42dd1bc1c1bd256a9a32890af1ae09b5MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese e estereoquímica de isoxazóis espiro-tetracíclicos trifluormetil substituídos |
dc.title.alternative.eng.fl_str_mv |
Synthesis and stereochemistry of trifluoromethyl substituted spiro-tetracyclic isoxazoles |
title |
Síntese e estereoquímica de isoxazóis espiro-tetracíclicos trifluormetil substituídos |
spellingShingle |
Síntese e estereoquímica de isoxazóis espiro-tetracíclicos trifluormetil substituídos Ketzer, Alex Química Química orgânica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese e estereoquímica de isoxazóis espiro-tetracíclicos trifluormetil substituídos |
title_full |
Síntese e estereoquímica de isoxazóis espiro-tetracíclicos trifluormetil substituídos |
title_fullStr |
Síntese e estereoquímica de isoxazóis espiro-tetracíclicos trifluormetil substituídos |
title_full_unstemmed |
Síntese e estereoquímica de isoxazóis espiro-tetracíclicos trifluormetil substituídos |
title_sort |
Síntese e estereoquímica de isoxazóis espiro-tetracíclicos trifluormetil substituídos |
author |
Ketzer, Alex |
author_facet |
Ketzer, Alex |
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 |
Iglesias, Bernardo Almeida |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/4402375533322977 |
dc.contributor.referee2.fl_str_mv |
Costa, Michele Budke |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/8752647892614261 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3038644206836878 |
dc.contributor.author.fl_str_mv |
Ketzer, Alex |
contributor_str_mv |
Bonacorso, Helio Gauze Iglesias, Bernardo Almeida Costa, Michele Budke |
dc.subject.por.fl_str_mv |
Química Química orgânica |
topic |
Química Química orgânica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The present dissertation initially describes methodologies for the synthesis of five 3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkan]-3-ols (7) in 65 – 84 % yields, where the spirocarbocyclic portion is constituted by: cyclopentane, cyclohexane, cycloheptane, 4-methyl-cyclohexane or 4-tert-butyl-cyclohexane. The isoxazolines 7 where synthesized through cyclocondensation [3+2] employing 2,2,2-trifluoro-1-(4-methoxyspiro[chromene-2,1'-cyclopentan]-3-yl)ethan-1-one (6) as the 1,3dieletrophile [CCC], and hydroxylamine chloridrate as the 1,2-dinucleophile [NO] in the presence of NaHCO3 in 65 – 84 % yields. The stereochemistry involved in the isoxazolines (7) synthesis was discussed and elucidated using 1H, 13C, 19F NMR, HMQC, HMBC e NOESY 2-D-NMR and single crystal X-ray diffraction. In sequence the 3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkan]-3-ols (7) were dehydrated aiming to furnish a novel series of five 3-(trifluoromethyl)spiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkanes] (8). The dehydration was successfully performed in benzene/thionyl chloride media in 76 – 95 % yields. In a next reaction step the isoxazolines (7) were derivativated with propargyl bromide through a NS2 reaction furnishing a novel heterocyclic series of five 3-(prop-2-yn-1-yloxy)-3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkanes] (10) in 71 – 84 % yields. Finally the isolated terminal alkynes were successfully employed in the construction of a series of five examples of 3-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1'-cycloalkanes] (12), in 36 – 84% yields. The methylene-bi-heterocyclic series (12), composed exclusively of 1,4-dissubstituted 1,2,3-triazoles, was obtained through a regoiselective 1,3 dipolar cycloaddition (Click Chemistry) catalyzed by copper iodide using terminal alkynes (10) and benzil Azide (NNN fragment). |
publishDate |
2017 |
dc.date.issued.fl_str_mv |
2017-02-23 |
dc.date.accessioned.fl_str_mv |
2018-08-13T12:38:00Z |
dc.date.available.fl_str_mv |
2018-08-13T12:38:00Z |
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.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/14045 |
url |
http://repositorio.ufsm.br/handle/1/14045 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 |
dc.relation.authority.fl_str_mv |
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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:Repositório Institucional Manancial UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
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institution |
UFSM |
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repository.name.fl_str_mv |
Repositório Institucional Manancial UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
ouvidoria@ufsm.br |
_version_ |
1808854726702268416 |