Síntese de derivados de dihidronafto[c]furanos e fenantrenos via processo de carbociclização intramolecular

Detalhes bibliográficos
Autor(a) principal: Grimaldi, Tamíris Bauer
Data de Publicação: 2016
Tipo de documento: Tese
Idioma: por
Título da fonte: Biblioteca Digital de Teses e Dissertações do UFSM
Texto Completo: http://repositorio.ufsm.br/handle/1/21563
Resumo: n this work, we reported the study developed for the preparation of substituted dihydronaphtho[c]furans and phenanthrenes via intramolecular cyclization process. Firstly, a variety of dihydronaphtho[c]furans 2 was prepared by the reaction of bis-propargyl ethers 1 with a catalytic amount of t-BuOK. Subsequently, the o-ethynyl-biphenyls 3 were subjected to carbocyclization reaction mediated by I2 and a catalytic amount of K2CO3, which allowed the synthesis of 9-iodo-10-organochalcogen-phenanthrenes 4. Yet, the o-ethynyl-biphenyls 3 carbocyclization reaction promoted by diorganyl diselenides and FeCl3, lead to 9- organochalcogen-phenanthrenes 5. The methodologies proceeded selectively, furnishing the products in good yields under mild reactions conditions.
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spelling 2021-07-22T17:11:25Z2021-07-22T17:11:25Z2016-11-25http://repositorio.ufsm.br/handle/1/21563n this work, we reported the study developed for the preparation of substituted dihydronaphtho[c]furans and phenanthrenes via intramolecular cyclization process. Firstly, a variety of dihydronaphtho[c]furans 2 was prepared by the reaction of bis-propargyl ethers 1 with a catalytic amount of t-BuOK. Subsequently, the o-ethynyl-biphenyls 3 were subjected to carbocyclization reaction mediated by I2 and a catalytic amount of K2CO3, which allowed the synthesis of 9-iodo-10-organochalcogen-phenanthrenes 4. Yet, the o-ethynyl-biphenyls 3 carbocyclization reaction promoted by diorganyl diselenides and FeCl3, lead to 9- organochalcogen-phenanthrenes 5. The methodologies proceeded selectively, furnishing the products in good yields under mild reactions conditions.Neste trabalho, relata-se o estudo desenvolvido para a preparação de dihidronafto[c]furanos e de fenantrenos substituídos via processo de carbociclização intramolecular. Primeiramente, uma variedade de dihidronafto[c]furanos 2 foi preparada através da reação dos éteres bis propargílicos 1 com quantidades catalíticas de t-BuOK. Posteriormente, os o-alquinil-bifenis 3 foram submetidos à reações de carbociclização mediadas por I2 e quantidades catalíticas de K2CO3, o que permitiu a síntese dos 9-iodo-10-organocalcogenofenantrenos 4. Ainda, a carbociclização dos o-alquinil-bifenis 3 promovida por dicalcogenetos de diorganoíla e FeCl3 levou aos 9-organocalcogenofenantrenos 5. As metodologias desenvolvidas mostraram-se seletivas, fornecendo os produtos bons rendimentos sob condições de reação brandas.porUniversidade 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/openAccessCarbociclizaçãoDihidronafto[c]furanosFenantrenosCarboyclizationDihydronaphtho[c]furansPhenanthrenesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de derivados de dihidronafto[c]furanos e fenantrenos via processo de carbociclização intramolecularSynthesis of dihydronaphtho[c]furans and phenanthrenes derivatives via intramolecular carbocyclizationinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisZeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937Iglesias, Bernardo AlmeidaAlberto, Eduardo EliezerRodrigues , Oscar Endrigo DornelesGuadagnin, Rafael Carloshttp://lattes.cnpq.br/6782777164952627Grimaldi, Tamíris Bauer10060000000060060060060060040bcc34b-9304-4b92-ba5d-b8aeb3962ae923304805-f4c2-4530-a066-156c61d38a59483d6d0c-e419-454b-b413-1a51673258c31fe49657-789d-4f5f-8746-a34cfd36a383e7f4492f-46f8-436e-b78d-5bee588e11e442c3c3a1-16cc-4545-8629-30fb5307df40reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv Síntese de derivados de dihidronafto[c]furanos e fenantrenos via processo de carbociclização intramolecular
dc.title.alternative.eng.fl_str_mv Synthesis of dihydronaphtho[c]furans and phenanthrenes derivatives via intramolecular carbocyclization
title Síntese de derivados de dihidronafto[c]furanos e fenantrenos via processo de carbociclização intramolecular
spellingShingle Síntese de derivados de dihidronafto[c]furanos e fenantrenos via processo de carbociclização intramolecular
Grimaldi, Tamíris Bauer
Carbociclização
Dihidronafto[c]furanos
Fenantrenos
Carboyclization
Dihydronaphtho[c]furans
Phenanthrenes
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese de derivados de dihidronafto[c]furanos e fenantrenos via processo de carbociclização intramolecular
title_full Síntese de derivados de dihidronafto[c]furanos e fenantrenos via processo de carbociclização intramolecular
title_fullStr Síntese de derivados de dihidronafto[c]furanos e fenantrenos via processo de carbociclização intramolecular
title_full_unstemmed Síntese de derivados de dihidronafto[c]furanos e fenantrenos via processo de carbociclização intramolecular
title_sort Síntese de derivados de dihidronafto[c]furanos e fenantrenos via processo de carbociclização intramolecular
author Grimaldi, Tamíris Bauer
author_facet Grimaldi, Tamíris Bauer
author_role author
dc.contributor.advisor1.fl_str_mv Zeni, Gilson Rogério
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/2355575631197937
dc.contributor.referee1.fl_str_mv Iglesias, Bernardo Almeida
dc.contributor.referee2.fl_str_mv Alberto, Eduardo Eliezer
dc.contributor.referee3.fl_str_mv Rodrigues , Oscar Endrigo Dorneles
dc.contributor.referee4.fl_str_mv Guadagnin, Rafael Carlos
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/6782777164952627
dc.contributor.author.fl_str_mv Grimaldi, Tamíris Bauer
contributor_str_mv Zeni, Gilson Rogério
Iglesias, Bernardo Almeida
Alberto, Eduardo Eliezer
Rodrigues , Oscar Endrigo Dorneles
Guadagnin, Rafael Carlos
dc.subject.por.fl_str_mv Carbociclização
Dihidronafto[c]furanos
Fenantrenos
topic Carbociclização
Dihidronafto[c]furanos
Fenantrenos
Carboyclization
Dihydronaphtho[c]furans
Phenanthrenes
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv Carboyclization
Dihydronaphtho[c]furans
Phenanthrenes
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description n this work, we reported the study developed for the preparation of substituted dihydronaphtho[c]furans and phenanthrenes via intramolecular cyclization process. Firstly, a variety of dihydronaphtho[c]furans 2 was prepared by the reaction of bis-propargyl ethers 1 with a catalytic amount of t-BuOK. Subsequently, the o-ethynyl-biphenyls 3 were subjected to carbocyclization reaction mediated by I2 and a catalytic amount of K2CO3, which allowed the synthesis of 9-iodo-10-organochalcogen-phenanthrenes 4. Yet, the o-ethynyl-biphenyls 3 carbocyclization reaction promoted by diorganyl diselenides and FeCl3, lead to 9- organochalcogen-phenanthrenes 5. The methodologies proceeded selectively, furnishing the products in good yields under mild reactions conditions.
publishDate 2016
dc.date.issued.fl_str_mv 2016-11-25
dc.date.accessioned.fl_str_mv 2021-07-22T17:11:25Z
dc.date.available.fl_str_mv 2021-07-22T17:11:25Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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Centro de Ciências Naturais e Exatas
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dc.publisher.department.fl_str_mv Química
publisher.none.fl_str_mv Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
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