Síntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinas
Ano de defesa: | 2005 |
---|---|
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: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/10634 |
Resumo: | This work describes the reactions of 1-methoxy-2-trifluoroacetyl-3,4-dihydro-naphthalene (4) with substituted anilines 5a-j to obtain a series of N-aril-2-trifluoroacetyl-3,4-diidronaphtalenes (6a-j). Intramolecular cyclization of 6a-j furnished a novel series of substituted 7-trifluoromethyl-5,6-dihydrobenzo[c]acridines (7a-j). Coumpond 4 was obtained from the trifluoroacetylation reaction of the mixture of acetal (2) and enoléter (3) derived from ketone α-tetralone (1) with trifluoroacetic anhydride. The reactions of 1-methoxy-2-trifluoroacetyl-3,4-dihydro-naphthalene (4) with anilines 5a-j, in molar ratio 1:1, were carried out in acetonitrile at 81oC for 6 hours leading to the compounds 6a-j in 68-87%. The synthesis of 7-trifluoromethyl-5,6-dihydrobenzo[c]acridines (7a-j) were carried out by intramolecular cyclization reaction of 6a-j in the presence of polyphosphoric acid (PPA), in abscence of organic solvent at 110oC for 24 hours, in 44-82%. Others Lewis acid such as TiCl4, ZnCl2, P2O5/POCl3, POCl3 or CF3COOH and triethylamine were employed to obtain 7a, however only the reactions using PPA gave positive results. |
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2017-05-222017-05-222005-02-28DREKENER, Roberta Lopes. Synthesis of 7-trifluoromethyl- 5,6-dihydrobenzo[c]acridines. 2005. 137 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2005.http://repositorio.ufsm.br/handle/1/10634This work describes the reactions of 1-methoxy-2-trifluoroacetyl-3,4-dihydro-naphthalene (4) with substituted anilines 5a-j to obtain a series of N-aril-2-trifluoroacetyl-3,4-diidronaphtalenes (6a-j). Intramolecular cyclization of 6a-j furnished a novel series of substituted 7-trifluoromethyl-5,6-dihydrobenzo[c]acridines (7a-j). Coumpond 4 was obtained from the trifluoroacetylation reaction of the mixture of acetal (2) and enoléter (3) derived from ketone α-tetralone (1) with trifluoroacetic anhydride. The reactions of 1-methoxy-2-trifluoroacetyl-3,4-dihydro-naphthalene (4) with anilines 5a-j, in molar ratio 1:1, were carried out in acetonitrile at 81oC for 6 hours leading to the compounds 6a-j in 68-87%. The synthesis of 7-trifluoromethyl-5,6-dihydrobenzo[c]acridines (7a-j) were carried out by intramolecular cyclization reaction of 6a-j in the presence of polyphosphoric acid (PPA), in abscence of organic solvent at 110oC for 24 hours, in 44-82%. Others Lewis acid such as TiCl4, ZnCl2, P2O5/POCl3, POCl3 or CF3COOH and triethylamine were employed to obtain 7a, however only the reactions using PPA gave positive results.Este trabalho descreve as reações de 1-metoxi-2-trifluoracetil-3,4-diidro-naftaleno (4) com anilinas substituídas 5a-j para obter uma série de N-aril-2-trifluoracetil-3,4-diidronaftalenos (6a-j). O composto 6a-j sofre reação de ciclização intramolecular formando uma nova série de 7-trifluormetil-5,6-diidrobenzo[c]acridinas (7a-j). O composto 4 foi obtido por reação de trifluoracetilação da mistura de compostos acetal 2 e enoléter 3 derivados da α-tetralona 1, com anidrido trifluoracético. A reação de 1-metoxi-2-trifluoracetil-3,4-diidro-naftaleno (4) com anilinas 5a-j, em quantidade molar 1:1, foi realizada em acetonitrila a 81oC por 6 horas levando aos compostos 6a-j em 68-78% de rendimento. A síntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinas (7a-j) foi realizada via reação de ciclização intramolecular de 6a-j na presença de ácido polifosfórico (PPA), sem solvente a 110oC por 24 horas, em 44-82%. Outros ácidos de Lewis como TiCl4, ZnCl2, P2O5/POCl3, POCl3 ou CF3COOH e trietilamina foram utilizados para obter 7a, entretanto somente a reação utilizando PPA levou a resultados positivos.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaQuímicaQuímica orgânicaCompostos orgânicosCompostos heterocíclicosCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinasSynthesis of 7-trifluoromethyl- 5,6-dihydrobenzo[c]acridinesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0Braga, Antonio Luizhttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788861Z7Zanatta, Nilohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783100P9http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4705798Y2Drekener, Roberta Lopes10060000000040050030050050006c852ad-d805-43c3-99d6-93a6a86f507cba9abca1-0ffd-4f4a-82c6-82bbaf70e0cb70895f0d-f6c9-4428-81ac-bad500be1dc52f7bd6ce-78fa-4968-ac66-2d1407e90f60info:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALROBERTADREKENER.pdfapplication/pdf3645328http://repositorio.ufsm.br/bitstream/1/10634/1/ROBERTADREKENER.pdf424f0158b509afe4a60c915563032b51MD51TEXTROBERTADREKENER.pdf.txtROBERTADREKENER.pdf.txtExtracted texttext/plain158418http://repositorio.ufsm.br/bitstream/1/10634/2/ROBERTADREKENER.pdf.txtcda357c0e538c0bfc25150756bd0d577MD52THUMBNAILROBERTADREKENER.pdf.jpgROBERTADREKENER.pdf.jpgIM Thumbnailimage/jpeg4307http://repositorio.ufsm.br/bitstream/1/10634/3/ROBERTADREKENER.pdf.jpg89e9d73da2312e9f8a5531fbda9ee2c0MD531/106342017-07-25 12:05:14.611oai:repositorio.ufsm.br:1/10634Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132017-07-25T15:05:14Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinas |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 7-trifluoromethyl- 5,6-dihydrobenzo[c]acridines |
title |
Síntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinas |
spellingShingle |
Síntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinas Drekener, Roberta Lopes Química Química orgânica Compostos orgânicos Compostos heterocíclicos CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinas |
title_full |
Síntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinas |
title_fullStr |
Síntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinas |
title_full_unstemmed |
Síntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinas |
title_sort |
Síntese de 7-trifluormetil-5,6-diidrobenzo[c]acridinas |
author |
Drekener, Roberta Lopes |
author_facet |
Drekener, Roberta Lopes |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0 |
dc.contributor.referee1.fl_str_mv |
Braga, Antonio Luiz |
dc.contributor.referee1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788861Z7 |
dc.contributor.referee2.fl_str_mv |
Zanatta, Nilo |
dc.contributor.referee2Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783100P9 |
dc.contributor.authorLattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4705798Y2 |
dc.contributor.author.fl_str_mv |
Drekener, Roberta Lopes |
contributor_str_mv |
Bonacorso, Helio Gauze Braga, Antonio Luiz Zanatta, Nilo |
dc.subject.por.fl_str_mv |
Química Química orgânica Compostos orgânicos Compostos heterocíclicos |
topic |
Química Química orgânica Compostos orgânicos Compostos heterocíclicos CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work describes the reactions of 1-methoxy-2-trifluoroacetyl-3,4-dihydro-naphthalene (4) with substituted anilines 5a-j to obtain a series of N-aril-2-trifluoroacetyl-3,4-diidronaphtalenes (6a-j). Intramolecular cyclization of 6a-j furnished a novel series of substituted 7-trifluoromethyl-5,6-dihydrobenzo[c]acridines (7a-j). Coumpond 4 was obtained from the trifluoroacetylation reaction of the mixture of acetal (2) and enoléter (3) derived from ketone α-tetralone (1) with trifluoroacetic anhydride. The reactions of 1-methoxy-2-trifluoroacetyl-3,4-dihydro-naphthalene (4) with anilines 5a-j, in molar ratio 1:1, were carried out in acetonitrile at 81oC for 6 hours leading to the compounds 6a-j in 68-87%. The synthesis of 7-trifluoromethyl-5,6-dihydrobenzo[c]acridines (7a-j) were carried out by intramolecular cyclization reaction of 6a-j in the presence of polyphosphoric acid (PPA), in abscence of organic solvent at 110oC for 24 hours, in 44-82%. Others Lewis acid such as TiCl4, ZnCl2, P2O5/POCl3, POCl3 or CF3COOH and triethylamine were employed to obtain 7a, however only the reactions using PPA gave positive results. |
publishDate |
2005 |
dc.date.issued.fl_str_mv |
2005-02-28 |
dc.date.accessioned.fl_str_mv |
2017-05-22 |
dc.date.available.fl_str_mv |
2017-05-22 |
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 |
DREKENER, Roberta Lopes. Synthesis of 7-trifluoromethyl- 5,6-dihydrobenzo[c]acridines. 2005. 137 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2005. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10634 |
identifier_str_mv |
DREKENER, Roberta Lopes. Synthesis of 7-trifluoromethyl- 5,6-dihydrobenzo[c]acridines. 2005. 137 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2005. |
url |
http://repositorio.ufsm.br/handle/1/10634 |
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Universidade Federal de Santa Maria |
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UFSM |
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Universidade Federal de Santa Maria |
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