Síntese sequencial linear de 6-((1,2,3-triazol-4-il)metil)-4,5- dimetil-2,6-di-hidro-1h-pirrolo[3,4-d]piridazinonas via reações de N-alquilação, CuAAC e ciclocondensação
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/15179 |
Resumo: | This dissertation presents a synthetic route for obtaining a series of eight 6-((1H-1,2,3- triazol-4-yl)methyl)-1H-pyrrolo[3,4-d]pyridazin-1-ones with yields of 40-70%. The synthetic route comprises three distinct steps: (i) N-alkylation reaction of polysubstituted pyrrole with propargyl bromide, (ii) Cu(I) catalyzed 1,3-dipolar cycloaddition reaction (CuAAC - copper(I)- catalyzedalkyne-azidecycloaddition) of system 1-(prop-2-yn-1-yl)-1H-pyrrole with some organic azides and (iii) [4+2] cyclocondensation reaction of carbonyl substituents of the pyrrole ring with hydrazine hydrochloride. Initially, we synthesized two examples of azido vinylesters aryl substituted by Knoevenagel condensation reaction between various aldehydes and methyl azidoacetate in 74- 92 % yields. Subsequently, we performed the [3+2] cycloaddition reaction between the azide vinylesters and acetylacetone, obtaining two examples od polysubstituted pyrroles using methyl 4-acetyl-5-methyl-2-phenyl-1H-pyrrole-3-carboxylate and methyl 4-acetyl-2-(4- methoxyphenyl)-5-methyl-1H-pyrrole-3-carboxylate as starting material. The two polysubstituted pyrroles were subjected to N-alkylation reaction with propargyl bromide, which were obtained in yields of 88 and 89%. Subsequently, eight examples of 1- (1H-1,2,3-triazol-4-yl)-1H-pyrroles in 48-88% yields were synthesized by CuAAC reaction between the two precursors and four organic azides, generated in situ by sodium azide and four different organic halides, namely, chloromethyl-benzene, 1-chloro-4-(chloromethyl)-benzene, 1- (chloromethyl)-4-methoxybenzene and 1-bromooctane. Thus, the eight target molecules (6- ((1H-1,2,3-triazol-4-yl)methyl)-1H-pyrrolo[3,4-d]pyridazin-1-ones) were obtained from a [4+2] cyclocondensation reaction between hydrazine hydrochloride and the methylcarboxylate and acetyl substituents present in positions 3 and 4 of the pyrrole rings. The structure of the compounds was characterized by combined techniques of NMR Spectroscopy (1H and 13C {1H}), Gas Chromatography coupled to Mass Spectrometry (GCMS), High Resolution Mass Spectrometry (HRMS) and X-ray Diffraction. |
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3913 |
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2019-01-02T11:26:17Z2019-01-02T11:26:17Z2017-09-21http://repositorio.ufsm.br/handle/1/15179This dissertation presents a synthetic route for obtaining a series of eight 6-((1H-1,2,3- triazol-4-yl)methyl)-1H-pyrrolo[3,4-d]pyridazin-1-ones with yields of 40-70%. The synthetic route comprises three distinct steps: (i) N-alkylation reaction of polysubstituted pyrrole with propargyl bromide, (ii) Cu(I) catalyzed 1,3-dipolar cycloaddition reaction (CuAAC - copper(I)- catalyzedalkyne-azidecycloaddition) of system 1-(prop-2-yn-1-yl)-1H-pyrrole with some organic azides and (iii) [4+2] cyclocondensation reaction of carbonyl substituents of the pyrrole ring with hydrazine hydrochloride. Initially, we synthesized two examples of azido vinylesters aryl substituted by Knoevenagel condensation reaction between various aldehydes and methyl azidoacetate in 74- 92 % yields. Subsequently, we performed the [3+2] cycloaddition reaction between the azide vinylesters and acetylacetone, obtaining two examples od polysubstituted pyrroles using methyl 4-acetyl-5-methyl-2-phenyl-1H-pyrrole-3-carboxylate and methyl 4-acetyl-2-(4- methoxyphenyl)-5-methyl-1H-pyrrole-3-carboxylate as starting material. The two polysubstituted pyrroles were subjected to N-alkylation reaction with propargyl bromide, which were obtained in yields of 88 and 89%. Subsequently, eight examples of 1- (1H-1,2,3-triazol-4-yl)-1H-pyrroles in 48-88% yields were synthesized by CuAAC reaction between the two precursors and four organic azides, generated in situ by sodium azide and four different organic halides, namely, chloromethyl-benzene, 1-chloro-4-(chloromethyl)-benzene, 1- (chloromethyl)-4-methoxybenzene and 1-bromooctane. Thus, the eight target molecules (6- ((1H-1,2,3-triazol-4-yl)methyl)-1H-pyrrolo[3,4-d]pyridazin-1-ones) were obtained from a [4+2] cyclocondensation reaction between hydrazine hydrochloride and the methylcarboxylate and acetyl substituents present in positions 3 and 4 of the pyrrole rings. The structure of the compounds was characterized by combined techniques of NMR Spectroscopy (1H and 13C {1H}), Gas Chromatography coupled to Mass Spectrometry (GCMS), High Resolution Mass Spectrometry (HRMS) and X-ray Diffraction.A dissertação apresenta uma rota sintética para a obtenção de uma série de oito 6-((1,2,3- triazol-4-il)metil)-4,5-dimetil-2,6-di-hidro-1H-pirrolo[3,4-d]piridazinonas com rendimentos de 40-70%. A rota sintética compreende três etapas distintas: (i) reação de N-alquilação de pirrol polissubstituído com brometo de propargila, (ii) reação de cicloadição 1,3-dipolar catalisada por Cu(I) (CuAAC - copper(I)-catalyzedalkyne-azidecycloaddition) do sistema 1- (prop-2-in-1-il)-1H-pirrol com azidas orgânicas e, por fim, (iii) reação de ciclocondensação [4+2] entre o cloridrato de hidrazina e funções carboniladas dos aneis pirrólicos envolvidos nesta dissertação. Inicialmente, foram sintetizados dois exemplos de azido vinilésteres aril substituídos por reação de condensação de Knoevenagel entre aldeídos e azido acetato de metila em rendimentos de 74-92%. Subsequentemente, foi realizada a reação de cicloadição [3+2] entre os diferentes azido vinilésteres e acetilacetona, obtendo dois exemplares de pirróis polissubstituídos empregados, na próxima etapa reacional, como materiais de partida: 4-acetil- 2-fenil-3-metilcarboxilato-5-metil-1H-pirrol e 4-acetil-2-(4-metoxifenil)-3-metilcarboxilato-5- metil-1H-pirrol. Os pirróis polissubstituídos foram, então, submetidos a reação de N-alquilação com brometo de propargila, obtendo-se os produtos respectivos em redimentos de 88 e 89% . Na sequência, foram sintetizados oito exemplos de 1-(1H-1,2,3-triazol-4-il)-1H-pirróis com rendimentos de 48-88%, através da reação tipo CuAAC entre os dois pirróis N-propargilados e quatro azidas orgânicas, geradas in situ a partir de azida de sódio com os seguintes haletos orgânicos: clorometil-benzeno, 1-cloro-4-(clorometil)-benzeno, 1-(clorometil)-4- metoxibenzeno e 1-bromo-octano. Finalmente, foram obtidas as oito moléculas alvo (6-((1- (aril))-1H-1,2,3-triazol-4-il)metil)-7-(aril)-2,6-dihidro-1H-pirrolo[3,4-d]piridazin-1-onas) a partir da reação de ciclocondensação [4+2] entre cloridrato de hidrazinas e 1-(1H-1,2,3-triazol- 4-il)-1H-pirróis contendo os substituintes metilcarboxilato e acetila nas posições 3 e 4 do anel pirrólico. A estrutura dos compostos foi caracterizada por técnicas de Espectroscopia de RMN de 1H, 13C {1H}, Cromatografia Gasosa acoplada à Espectrometria de Massas (CG-EM), Espectrometria de Massas de Alta Resolução (HMRS) e Difração de Raios-X.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/openAccessPirróisTriazóisPirrolo[3,4-d]piridazinonasN-alquilaçãoCuAACReação de ciclocondensação [4+2] com hidrazinasHClPyrrolesTriazolesPyrrolo[3,4-d]pyridazinonesN-alkylationCuAAC[4+2] cyclocondesation reaction with hydrazineCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese sequencial linear de 6-((1,2,3-triazol-4-il)metil)-4,5- dimetil-2,6-di-hidro-1h-pirrolo[3,4-d]piridazinonas via reações de N-alquilação, CuAAC e ciclocondensaçãoLinear synthesis of 6-((1,2,3-triazol-4-yl)methyl)-4,5-dimethyl-2,6- dihydro-1h-pyrrolo[3,4-d]pyridazinones via reactions of N-alquilation, CuAAC and ciclocondensationinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Frizzo, Clarissa Piccininhttp://lattes.cnpq.br/0029279904716491Fantinel, Leonardohttp://lattes.cnpq.br/3934644027018397http://lattes.cnpq.br/5038404227461961Magalhães, Hernane Tolentino10060000000060050006c852ad-d805-43c3-99d6-93a6a86f507c4214143c-9c00-4e23-96f3-1eef26a7fe7cbf4338e5-e87c-4326-93b7-60f8f505f4663cd76448-fb79-4eef-964a-72648182483creponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2017_MAGALHAES_HERNANE.pdfDIS_PPGQUIMICA_2017_MAGALHAES_HERNANE.pdfDissertação de Mestradoapplication/pdf7661195http://repositorio.ufsm.br/bitstream/1/15179/1/DIS_PPGQUIMICA_2017_MAGALHAES_HERNANE.pdfe12ff2a51b639462d8aec2e5accfbeb8MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese sequencial linear de 6-((1,2,3-triazol-4-il)metil)-4,5- dimetil-2,6-di-hidro-1h-pirrolo[3,4-d]piridazinonas via reações de N-alquilação, CuAAC e ciclocondensação |
dc.title.alternative.eng.fl_str_mv |
Linear synthesis of 6-((1,2,3-triazol-4-yl)methyl)-4,5-dimethyl-2,6- dihydro-1h-pyrrolo[3,4-d]pyridazinones via reactions of N-alquilation, CuAAC and ciclocondensation |
title |
Síntese sequencial linear de 6-((1,2,3-triazol-4-il)metil)-4,5- dimetil-2,6-di-hidro-1h-pirrolo[3,4-d]piridazinonas via reações de N-alquilação, CuAAC e ciclocondensação |
spellingShingle |
Síntese sequencial linear de 6-((1,2,3-triazol-4-il)metil)-4,5- dimetil-2,6-di-hidro-1h-pirrolo[3,4-d]piridazinonas via reações de N-alquilação, CuAAC e ciclocondensação Magalhães, Hernane Tolentino Pirróis Triazóis Pirrolo[3,4-d]piridazinonas N-alquilação CuAAC Reação de ciclocondensação [4+2] com hidrazinas HCl Pyrroles Triazoles Pyrrolo[3,4-d]pyridazinones N-alkylation CuAAC [4+2] cyclocondesation reaction with hydrazine CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese sequencial linear de 6-((1,2,3-triazol-4-il)metil)-4,5- dimetil-2,6-di-hidro-1h-pirrolo[3,4-d]piridazinonas via reações de N-alquilação, CuAAC e ciclocondensação |
title_full |
Síntese sequencial linear de 6-((1,2,3-triazol-4-il)metil)-4,5- dimetil-2,6-di-hidro-1h-pirrolo[3,4-d]piridazinonas via reações de N-alquilação, CuAAC e ciclocondensação |
title_fullStr |
Síntese sequencial linear de 6-((1,2,3-triazol-4-il)metil)-4,5- dimetil-2,6-di-hidro-1h-pirrolo[3,4-d]piridazinonas via reações de N-alquilação, CuAAC e ciclocondensação |
title_full_unstemmed |
Síntese sequencial linear de 6-((1,2,3-triazol-4-il)metil)-4,5- dimetil-2,6-di-hidro-1h-pirrolo[3,4-d]piridazinonas via reações de N-alquilação, CuAAC e ciclocondensação |
title_sort |
Síntese sequencial linear de 6-((1,2,3-triazol-4-il)metil)-4,5- dimetil-2,6-di-hidro-1h-pirrolo[3,4-d]piridazinonas via reações de N-alquilação, CuAAC e ciclocondensação |
author |
Magalhães, Hernane Tolentino |
author_facet |
Magalhães, Hernane Tolentino |
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 |
Frizzo, Clarissa Piccinin |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/0029279904716491 |
dc.contributor.referee2.fl_str_mv |
Fantinel, Leonardo |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/3934644027018397 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5038404227461961 |
dc.contributor.author.fl_str_mv |
Magalhães, Hernane Tolentino |
contributor_str_mv |
Bonacorso, Helio Gauze Frizzo, Clarissa Piccinin Fantinel, Leonardo |
dc.subject.por.fl_str_mv |
Pirróis Triazóis Pirrolo[3,4-d]piridazinonas N-alquilação CuAAC Reação de ciclocondensação [4+2] com hidrazinas HCl |
topic |
Pirróis Triazóis Pirrolo[3,4-d]piridazinonas N-alquilação CuAAC Reação de ciclocondensação [4+2] com hidrazinas HCl Pyrroles Triazoles Pyrrolo[3,4-d]pyridazinones N-alkylation CuAAC [4+2] cyclocondesation reaction with hydrazine CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Pyrroles Triazoles Pyrrolo[3,4-d]pyridazinones N-alkylation CuAAC [4+2] cyclocondesation reaction with hydrazine |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This dissertation presents a synthetic route for obtaining a series of eight 6-((1H-1,2,3- triazol-4-yl)methyl)-1H-pyrrolo[3,4-d]pyridazin-1-ones with yields of 40-70%. The synthetic route comprises three distinct steps: (i) N-alkylation reaction of polysubstituted pyrrole with propargyl bromide, (ii) Cu(I) catalyzed 1,3-dipolar cycloaddition reaction (CuAAC - copper(I)- catalyzedalkyne-azidecycloaddition) of system 1-(prop-2-yn-1-yl)-1H-pyrrole with some organic azides and (iii) [4+2] cyclocondensation reaction of carbonyl substituents of the pyrrole ring with hydrazine hydrochloride. Initially, we synthesized two examples of azido vinylesters aryl substituted by Knoevenagel condensation reaction between various aldehydes and methyl azidoacetate in 74- 92 % yields. Subsequently, we performed the [3+2] cycloaddition reaction between the azide vinylesters and acetylacetone, obtaining two examples od polysubstituted pyrroles using methyl 4-acetyl-5-methyl-2-phenyl-1H-pyrrole-3-carboxylate and methyl 4-acetyl-2-(4- methoxyphenyl)-5-methyl-1H-pyrrole-3-carboxylate as starting material. The two polysubstituted pyrroles were subjected to N-alkylation reaction with propargyl bromide, which were obtained in yields of 88 and 89%. Subsequently, eight examples of 1- (1H-1,2,3-triazol-4-yl)-1H-pyrroles in 48-88% yields were synthesized by CuAAC reaction between the two precursors and four organic azides, generated in situ by sodium azide and four different organic halides, namely, chloromethyl-benzene, 1-chloro-4-(chloromethyl)-benzene, 1- (chloromethyl)-4-methoxybenzene and 1-bromooctane. Thus, the eight target molecules (6- ((1H-1,2,3-triazol-4-yl)methyl)-1H-pyrrolo[3,4-d]pyridazin-1-ones) were obtained from a [4+2] cyclocondensation reaction between hydrazine hydrochloride and the methylcarboxylate and acetyl substituents present in positions 3 and 4 of the pyrrole rings. The structure of the compounds was characterized by combined techniques of NMR Spectroscopy (1H and 13C {1H}), Gas Chromatography coupled to Mass Spectrometry (GCMS), High Resolution Mass Spectrometry (HRMS) and X-ray Diffraction. |
publishDate |
2017 |
dc.date.issued.fl_str_mv |
2017-09-21 |
dc.date.accessioned.fl_str_mv |
2019-01-02T11:26:17Z |
dc.date.available.fl_str_mv |
2019-01-02T11:26:17Z |
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/1/15179 |
url |
http://repositorio.ufsm.br/handle/1/15179 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 500 |
dc.relation.authority.fl_str_mv |
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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 |
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Universidade Federal de Santa Maria (UFSM) |
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UFSM |
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UFSM |
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Manancial - Repositório Digital da UFSM |
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Manancial - Repositório Digital da UFSM |
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Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM) |
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