S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico

Bernardes, Bauer de Oliveira

S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico

Detalhes bibliográficos
Ano de defesa:	2012
Autor(a) principal:	Bernardes, Bauer de Oliveira
Orientador(a):	Ferreira, Aur?lio Baird Buarque
Banca de defesa:	Silva, Francisco de Assis da, Mello, Helo?sa de, Ferreira, Jos? Carlos Netto, Garden, Simon John
Tipo de documento:	Tese
Tipo de acesso:	Acesso aberto
Idioma:	por
Instituição de defesa:	Universidade Federal Rural do Rio de Janeiro
Programa de Pós-Graduação:	Programa de P?s-Gradua??o em Qu?mica
Departamento:	Instituto de Ci?ncias Exatas
País:	Brasil
Palavras-chave em Português:	?-lapachona naftoquinonas cicloadi??es
Palavras-chave em Inglês:	?-lapachone naphthoquinones cycloaddition
Área do conhecimento CNPq:	Qu?mica
Link de acesso:	https://tede.ufrrj.br/jspui/handle/jspui/3530
Resumo:	In this work we investigated the reactivity of the quinones lapachol, ?-lapachone, 2- methoxy-lapachol and mainly ?-lapachone. It was found that diazocompounds react with ?-lapachone with formation of dioxolanes, but with diazomethane an oxirane and an aldehyde were also formed, depending on the reaction conditions. Dioxolanes were also made from nitroalkanes by reaction with ?-lapachone, but nitromethane was unreactive. We have made theoretical calculations to compare the reactivity of different nitroalkanes and Grignard compounds with this quinone. Reactions with vicinal diamines led to different phenazines and quinoxalines, some unpublished. Photochemical reactions with different systems olefinic were observed in type cycloaddition [4 +2], notably the reaction with 5,6-diphenyl-2,3-dihydro-1,4-dioxin product which provided a yield of 96% and we not isolate products by cycloaddition [2 +2]. We observed the characteristic of ?-lapachone in transferring energy through the dimerization of acenaphthylene and also isolated a novel aldehyde in the reaction with 2,3-dihydro-1 ,4-dioxin. Laser flash photolysis of quinones ?-, ?-, nor-?- and 3-sulfo-?- lapachone was used to characterize and study the properties and reactivity of the triplet excited state of these quinones. Different vicinal diamines reacted with ?-lapachone to form new quinoxalines and phenazines. Reduction reactions followed by acetylation or alkylation were performed with lapachol, ?-, ?-lapachone and 2-methoxy-lapachol, and the use of pyridine latter quinone provided mainly ?-xiloidona. The ?-lapachone subjected to LiAlH4 or NaBH4 followed by benzoyl bromide gave a tertiary alcohol, previously only obtained via Grignard reaction by our group. Distinct methodologies were used in attempting the nitration products obtained, such as esters, ethers or dioxin or dioxolane ring, but in almost all cases there was a return to quinone form. Under the conditions of Laszlo dioxin DXBL formed a novel acetal. The compounds obtained were analyzed by mass spectrometry, nuclear magnetic resonance spectroscopy of carbon-13 and hydrogen-1, infrared and / or X-ray diffraction.

Metadados do item

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spelling	Ferreira, Aur?lio Baird Buarque237.924.007-82http://lattes.cnpq.br/5526484175547597Silva, Francisco de Assis daMello, Helo?sa deFerreira, Jos? Carlos NettoGarden, Simon John041.532.457-64http://lattes.cnpq.br/8988332784422026Bernardes, Bauer de Oliveira2020-05-18T14:30:42Z2012-11-21BERNARDES, Bauer de Oliveira. S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico. 2012. 348 f. Tese (Doutorado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2012.https://tede.ufrrj.br/jspui/handle/jspui/3530In this work we investigated the reactivity of the quinones lapachol, ?-lapachone, 2- methoxy-lapachol and mainly ?-lapachone. It was found that diazocompounds react with ?-lapachone with formation of dioxolanes, but with diazomethane an oxirane and an aldehyde were also formed, depending on the reaction conditions. Dioxolanes were also made from nitroalkanes by reaction with ?-lapachone, but nitromethane was unreactive. We have made theoretical calculations to compare the reactivity of different nitroalkanes and Grignard compounds with this quinone. Reactions with vicinal diamines led to different phenazines and quinoxalines, some unpublished. Photochemical reactions with different systems olefinic were observed in type cycloaddition [4 +2], notably the reaction with 5,6-diphenyl-2,3-dihydro-1,4-dioxin product which provided a yield of 96% and we not isolate products by cycloaddition [2 +2]. We observed the characteristic of ?-lapachone in transferring energy through the dimerization of acenaphthylene and also isolated a novel aldehyde in the reaction with 2,3-dihydro-1 ,4-dioxin. Laser flash photolysis of quinones ?-, ?-, nor-?- and 3-sulfo-?- lapachone was used to characterize and study the properties and reactivity of the triplet excited state of these quinones. Different vicinal diamines reacted with ?-lapachone to form new quinoxalines and phenazines. Reduction reactions followed by acetylation or alkylation were performed with lapachol, ?-, ?-lapachone and 2-methoxy-lapachol, and the use of pyridine latter quinone provided mainly ?-xiloidona. The ?-lapachone subjected to LiAlH4 or NaBH4 followed by benzoyl bromide gave a tertiary alcohol, previously only obtained via Grignard reaction by our group. Distinct methodologies were used in attempting the nitration products obtained, such as esters, ethers or dioxin or dioxolane ring, but in almost all cases there was a return to quinone form. Under the conditions of Laszlo dioxin DXBL formed a novel acetal. The compounds obtained were analyzed by mass spectrometry, nuclear magnetic resonance spectroscopy of carbon-13 and hydrogen-1, infrared and / or X-ray diffraction.Neste trabalho exploramos a s?ntese de dioxolanos, dioxinas, ?steres, ?teres e fenazinas a partir das quinonas lapachol, ?-lapachona, 2-met?xi-lapachol e, principalmente, ?-lapachona. Verificamos que a ?-lapachona pode formar dioxolano a partir de diazompostos ou nitroalcanos. Estudamos rea??es fotoqu?micas entre o-quinonas e diferentes sistemas olef?nicos, onde observamos cicloadi??es do tipo [4+2], forma??o de um alde?do in?dito na rea??o com 2,3-di-hidro-1,4-dioxina, e a caracter?stica da ?-lapachona em transferir energia atrav?s da dimeriza??o do acenaftileno. Al?m disso, fot?lise por pulso de laser das quinonas ?-, ?-, nor-?- e 3-sulfo-?-lapachona foi usada para caracterizar e estudar a reatividade e propriedades do estado excitado triplete destas quinonas. Rea??es de redu??o seguidas de acetila??o ou alquila??o foram realizadas com lapachol, ?-, ?-lapachona e 2-met?xi-lapachol, e o uso de piridina nesta ?ltima quinona forneceu principalmente a ?-xiloidona. A ?-lapachona submetida ao NaBH4 ou LiAlH4 seguido de brometo de benzila forneceu um ?lcool terci?rio, s? obtido anteriormente por nosso grupo, atrav?s de rea??o de Grignard. Novas fenazinas e quinoxalinas foram formadas por rea??es com diaminas vicinais. Aplicamos metodologias distintas na tentativa de nitra??o dos ?steres, ?teres, dioxina ou dioxolano formados a partir das quinonas, mas em quase todos os casos houve retorno a forma quin?nica; Nas condi??es de Laszlo uma dioxina formou um acetal in?dito. Os compostos obtidos foram analisados por espectrometria de massa, espectroscopia de resson?ncia magn?tica nuclear de carbono-13 e hidrog?nio-1, infravermelho e/ou difra??o de raio-X.Submitted by Sandra Pereira (srpereira@ufrrj.br) on 2020-05-18T14:30:42Z No. of bitstreams: 1 2012 - Bauer de Oliveira Bernardes.pdf: 26455317 bytes, checksum: 00a0134e16b9ac8c75310f952830c6af (MD5)Made available in DSpace on 2020-05-18T14:30:42Z (GMT). No. of bitstreams: 1 2012 - Bauer de Oliveira Bernardes.pdf: 26455317 bytes, checksum: 00a0134e16b9ac8c75310f952830c6af (MD5) Previous issue date: 2012-11-21Conselho Nacional de Desenvolvimento Cient?fico e Tecnol?gico, CNPq, Brasil.application/pdfhttps://tede.ufrrj.br/retrieve/54364/2012%20-%20Bauer%20de%20Oliveira%20Bernardes.pdf.jpghttps://tede.ufrrj.br/retrieve/63744/2012%20-%20Bauer%20de%20Oliveira%20Bernardes%20%28Parte%201%20-%20Principal%29.pdf.jpghttps://tede.ufrrj.br/retrieve/63746/2012%20-%20Bauer%20de%20Oliveira%20Bernardes%20%28Parte%202%20-%20Anexos%29.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Ci?ncias ExatasABREU, F.C., FERREIRA, D.C.M., GOULART, M.O.F., BURIEZ, O. e AMATORE, C.. Eletrochemical activation of ?-lapachone in ?-cyclodextrin inclusion complexes and reactivity of its reduced form towards oxygen in aqueous solutions ? J. Electroanal. Chem., 608, p125-132, 2007. ABREU, F.C., FERREIRA, D.C.M., WADHAWAN, J., AMATORE, C., FERREIRA, V.F., SILVA, M.N., SOUZA, M.C.B.V., GOMES, T.S., XIMENES, E.A. e GOULART, M.O.F.. Eletrochemistry of ?-lapachone and its diazoderivative: Relevance to their compared antimicrobial activites ? Electrochem. Commun., 7, p767-72, 2005. AL-AZMI, A., ELASSAR, A.Z.A. e BOOTH, B. L.. The chemistry of diaminomaleonitrile and its utility in heterocyclic synthesis. Tetrahedron, 59, p2749-63, 2003. ALEGR?A, A.E., SANCHEZ-CRUZ, P. e RIVAS, L.. Alkaline-earth c?tions enhance ortho-quinone-catalyzed ascorbate oxidation. Free Radical Biol. Med., 37, p1631-9, 2004. ALI, R. M. , HOUGHTON, P. J. e HOO, T. S.. Antifungal activity of some bignoniacea found in Malaysia. Phytother. Res., 12(5), p331-4, 1998. ALMEIDA, L.S., VILLEGAS, R.A.S. e RIBEIRO, C.M.. Estudo da ciclofuncionaliza??o do lapachol com triacetato de t?lio. In: 24? RA-SBQ, Po?os de Caldas, 2001. ALVES, G.B.C., LOPES, R.S.C., LOPES, C.C. E SNIECKUS, V. ? 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ZIMMERMANN, M, WEHRLI, W e SCHMIDTRUPPIN, KH ? Alkylidenedioxy compounds, Pedido de patente EP 0,184,990,A1, 1985.?-lapachonanaftoquinonascicloadi??es?-lapachonenaphthoquinonescycloadditionQu?micaS?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nicoSynthesis of quinone derivatives of lapachol, ?- and ?-lapachone. 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dc.title.por.fl_str_mv	S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico
dc.title.alternative.eng.fl_str_mv	Synthesis of quinone derivatives of lapachol, ?- and ?-lapachone. Exploring the system quinone
title	S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico
spellingShingle	S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico Bernardes, Bauer de Oliveira ?-lapachona naftoquinonas cicloadi??es ?-lapachone naphthoquinones cycloaddition Qu?mica
title_short	S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico
title_full	S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico
title_fullStr	S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico
title_full_unstemmed	S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico
title_sort	S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico
author	Bernardes, Bauer de Oliveira
author_facet	Bernardes, Bauer de Oliveira
author_role	author
dc.contributor.advisor1.fl_str_mv	Ferreira, Aur?lio Baird Buarque
dc.contributor.advisor1ID.fl_str_mv	237.924.007-82
dc.contributor.advisor1Lattes.fl_str_mv	http://lattes.cnpq.br/5526484175547597
dc.contributor.referee1.fl_str_mv	Silva, Francisco de Assis da
dc.contributor.referee2.fl_str_mv	Mello, Helo?sa de
dc.contributor.referee3.fl_str_mv	Ferreira, Jos? Carlos Netto
dc.contributor.referee4.fl_str_mv	Garden, Simon John
dc.contributor.authorID.fl_str_mv	041.532.457-64
dc.contributor.authorLattes.fl_str_mv	http://lattes.cnpq.br/8988332784422026
dc.contributor.author.fl_str_mv	Bernardes, Bauer de Oliveira
contributor_str_mv	Ferreira, Aur?lio Baird Buarque Silva, Francisco de Assis da Mello, Helo?sa de Ferreira, Jos? Carlos Netto Garden, Simon John
dc.subject.por.fl_str_mv	?-lapachona naftoquinonas cicloadi??es
topic	?-lapachona naftoquinonas cicloadi??es ?-lapachone naphthoquinones cycloaddition Qu?mica
dc.subject.eng.fl_str_mv	?-lapachone naphthoquinones cycloaddition
dc.subject.cnpq.fl_str_mv	Qu?mica
description	In this work we investigated the reactivity of the quinones lapachol, ?-lapachone, 2- methoxy-lapachol and mainly ?-lapachone. It was found that diazocompounds react with ?-lapachone with formation of dioxolanes, but with diazomethane an oxirane and an aldehyde were also formed, depending on the reaction conditions. Dioxolanes were also made from nitroalkanes by reaction with ?-lapachone, but nitromethane was unreactive. We have made theoretical calculations to compare the reactivity of different nitroalkanes and Grignard compounds with this quinone. Reactions with vicinal diamines led to different phenazines and quinoxalines, some unpublished. Photochemical reactions with different systems olefinic were observed in type cycloaddition [4 +2], notably the reaction with 5,6-diphenyl-2,3-dihydro-1,4-dioxin product which provided a yield of 96% and we not isolate products by cycloaddition [2 +2]. We observed the characteristic of ?-lapachone in transferring energy through the dimerization of acenaphthylene and also isolated a novel aldehyde in the reaction with 2,3-dihydro-1 ,4-dioxin. Laser flash photolysis of quinones ?-, ?-, nor-?- and 3-sulfo-?- lapachone was used to characterize and study the properties and reactivity of the triplet excited state of these quinones. Different vicinal diamines reacted with ?-lapachone to form new quinoxalines and phenazines. Reduction reactions followed by acetylation or alkylation were performed with lapachol, ?-, ?-lapachone and 2-methoxy-lapachol, and the use of pyridine latter quinone provided mainly ?-xiloidona. The ?-lapachone subjected to LiAlH4 or NaBH4 followed by benzoyl bromide gave a tertiary alcohol, previously only obtained via Grignard reaction by our group. Distinct methodologies were used in attempting the nitration products obtained, such as esters, ethers or dioxin or dioxolane ring, but in almost all cases there was a return to quinone form. Under the conditions of Laszlo dioxin DXBL formed a novel acetal. The compounds obtained were analyzed by mass spectrometry, nuclear magnetic resonance spectroscopy of carbon-13 and hydrogen-1, infrared and / or X-ray diffraction.
publishDate	2012
dc.date.issued.fl_str_mv	2012-11-21
dc.date.accessioned.fl_str_mv	2020-05-18T14:30:42Z
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.citation.fl_str_mv	BERNARDES, Bauer de Oliveira. S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico. 2012. 348 f. Tese (Doutorado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2012.
dc.identifier.uri.fl_str_mv	https://tede.ufrrj.br/jspui/handle/jspui/3530
identifier_str_mv	BERNARDES, Bauer de Oliveira. S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico. 2012. 348 f. Tese (Doutorado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2012.
url	https://tede.ufrrj.br/jspui/handle/jspui/3530
dc.language.iso.fl_str_mv	por
language	por
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S?ntese de derivados das quinonas lapachol, ?- e ?-lapachona. Explorando o sistema quin?nico

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