Hidazida 6-hidrazinonicotínica: síntese quimio e regiosseletiva de piridinohidrazonas, ácidos pirazolil-nicotínicos e heterociclos derivados
Ano de defesa: | 2012 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , |
Tipo de documento: | Tese |
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/1/4220 |
Resumo: | The present research firstly describes the study of methods for the hydrolysis of amide bond [C(O)-N] in 2-(5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)-5-(5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl-1-carbonyl)pyridines (2), where alkyl = CH3, aryl = C6H5, 4-OCH3C6H4, 4,4 -BiPh and heteroaryl = fur-2-yl, previously synthesized, aiming at the synthesis of a series of five pyrazolyl-nicotinic acids (3), applying basic conditions (NaOH, EtOH/H2O, 100 oC, 20 h) and their five esters derivatives (4) through reactions of 3 with thionyl chloride and methanol. These compounds were successfully obtained and in pure form with yields of 70 95% for nicotinic acids and between 57 84% for the aforementioned esters. Secondly, the study of the reactivity of 6-hydrazinonicotinic acid hydrazide reagent was developed (1), which presents two different nucleophilic centers in its chemical structure: hydrazine and hydrazide. First, a cyclocondensation reaction of [4+1] type was conducted between 1 and the triethylorthoacetate. This ortho ester, acting as reagent / solvent under reflux for 16 hours, presented no chemical distinction between the two nucleophilic centers in 1, which simultaneously reacted, originating the novel heterocyclic system 3-methyl-6-(5-methyl -1,3,4-oxadiazol-2-yl-[1,2,4] triazolo[4,3-a]pyridine in 82% yield. The chemo-differentiation reactivity of the hydrazine-hydrazide moieties favoring hydrazine function was observed when 1 reacted with aryl and heteroaryl aldehydes in ethanol solvent at 60 °C for 7 hours, resulting in a series of seven new 6-[2-aryl/heteroarylmethylidenehydrazinyl]nicotinohydrazides (7) with 64 - 94% yields. Subsequently, the cyclocondensation reactions of [3 + 2] type involving the hydrazide 7 free function and the 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones (8) resulted in a new series of nine 5-[(3-alkyl(aryl/heteroaryl)-5- trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)carbonylpyridin-2-yl]aryl/ heteroarylaldehyde hydrazones (9) with 45 74% yields. Illustrating the possibility of obtaining other heterocycles, the 6-[2-aryl/heteroarylmethylidenehydrazinyl]nicotinohydrazides, which presents free hydrazide function, and triethylorthoacetate were used as predecessors. Therefore, the oxadiazolyl-pyridine (10) 2-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-pyridin-2-yl]-4-chlorobenzaldehyde hydrazone was obtained in 64% yield when this reaction was developed under reflux for 16 hours. Finally, with the intention of demonstrating the possibility of incorporating the metallocene ferrocene into the organic heterocyclic system under investigation, two 6-[2-ferrocenylmethyl(ethyl)idenehydrazino]nicotinic hydrazide (12) were synthesized with yields from 58 to 72% and a derived series from six 5-[(3-alkyl(aryl/heteroaryl)-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)carbonylpyridin-2-yl] acetylferrocene/ferrocenecarboxaldehyde hydrazones (13) with yields from 58 to 72%. The compounds were characterized by 1H and 13C {1H} NMR Spectroscopy, Gas Chromatography coupled to Mass Spectrometry (GC-MS), Liquid Chromatography coupled to Mass Spectrometry (LC-ESI-MS/MS) and their purity determined by CHN Elemental Analysis. |
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2017-05-162017-05-162012-04-20PAIM, Gisele Rocha. 6-Hydrazinonicotinic acid hydrazide: chemo and regioselective synthesis of pyridine-hydrazones, pyrazolyl-nicotinic acids and heterocyclic derivatives. 2012. 253 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2012.http://repositorio.ufsm.br/handle/1/4220The present research firstly describes the study of methods for the hydrolysis of amide bond [C(O)-N] in 2-(5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)-5-(5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl-1-carbonyl)pyridines (2), where alkyl = CH3, aryl = C6H5, 4-OCH3C6H4, 4,4 -BiPh and heteroaryl = fur-2-yl, previously synthesized, aiming at the synthesis of a series of five pyrazolyl-nicotinic acids (3), applying basic conditions (NaOH, EtOH/H2O, 100 oC, 20 h) and their five esters derivatives (4) through reactions of 3 with thionyl chloride and methanol. These compounds were successfully obtained and in pure form with yields of 70 95% for nicotinic acids and between 57 84% for the aforementioned esters. Secondly, the study of the reactivity of 6-hydrazinonicotinic acid hydrazide reagent was developed (1), which presents two different nucleophilic centers in its chemical structure: hydrazine and hydrazide. First, a cyclocondensation reaction of [4+1] type was conducted between 1 and the triethylorthoacetate. This ortho ester, acting as reagent / solvent under reflux for 16 hours, presented no chemical distinction between the two nucleophilic centers in 1, which simultaneously reacted, originating the novel heterocyclic system 3-methyl-6-(5-methyl -1,3,4-oxadiazol-2-yl-[1,2,4] triazolo[4,3-a]pyridine in 82% yield. The chemo-differentiation reactivity of the hydrazine-hydrazide moieties favoring hydrazine function was observed when 1 reacted with aryl and heteroaryl aldehydes in ethanol solvent at 60 °C for 7 hours, resulting in a series of seven new 6-[2-aryl/heteroarylmethylidenehydrazinyl]nicotinohydrazides (7) with 64 - 94% yields. Subsequently, the cyclocondensation reactions of [3 + 2] type involving the hydrazide 7 free function and the 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones (8) resulted in a new series of nine 5-[(3-alkyl(aryl/heteroaryl)-5- trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)carbonylpyridin-2-yl]aryl/ heteroarylaldehyde hydrazones (9) with 45 74% yields. Illustrating the possibility of obtaining other heterocycles, the 6-[2-aryl/heteroarylmethylidenehydrazinyl]nicotinohydrazides, which presents free hydrazide function, and triethylorthoacetate were used as predecessors. Therefore, the oxadiazolyl-pyridine (10) 2-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-pyridin-2-yl]-4-chlorobenzaldehyde hydrazone was obtained in 64% yield when this reaction was developed under reflux for 16 hours. Finally, with the intention of demonstrating the possibility of incorporating the metallocene ferrocene into the organic heterocyclic system under investigation, two 6-[2-ferrocenylmethyl(ethyl)idenehydrazino]nicotinic hydrazide (12) were synthesized with yields from 58 to 72% and a derived series from six 5-[(3-alkyl(aryl/heteroaryl)-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)carbonylpyridin-2-yl] acetylferrocene/ferrocenecarboxaldehyde hydrazones (13) with yields from 58 to 72%. The compounds were characterized by 1H and 13C {1H} NMR Spectroscopy, Gas Chromatography coupled to Mass Spectrometry (GC-MS), Liquid Chromatography coupled to Mass Spectrometry (LC-ESI-MS/MS) and their purity determined by CHN Elemental Analysis.Este trabalho descreve, inicialmente, o estudo de métodos de hidrólise para a ligação amídica [C(O)-N] em 2-[3-alquil(aril/heteroaril)-5-hidróxi-5-trifluormetil-4,5-diidro-1H-pirazol-1-il]-5-[3-alquil(aril/heteroaril)-5-hidróxi-5-trifluormetil-4,5-diidro-1H-carbonilpirazol-1-il]piridinas (2), sendo alquila = CH3, arila = C6H5, 4-OCH3C6H4, 4,4 -BiPh e heteroarila = Fur-2-ila, sintetizados previamente, visando a síntese de uma séries de cinco ácidos pirazolil-nicotínicos (3), empregando meio básico (NaOH, EtOH/H2O, 100 oC, 20 h) e seus respectivos cinco ésteres derivados (4) a partir de reações de 3 com SOCl2 e MeOH. Estes compostos foram obtidos com sucesso e de forma pura com rendimentos de 70 95% para os ácidos nicotínicos e entre 57 84% para os ésteres mencionados. Dando prosseguimento, realizou-se o estudo da diferenciação da reatividade do reagente hidrazida 6-hidrazinonicotínica (1), o qual possui em sua estrutura química dois centros nucleofílicos distintos: uma hidrazina e uma hidrazida. Primeiramente, foi executada uma reação de ciclocondensação do tipo [4+1] entre 1 e ortoacetato de trietila. Este orto-éster atuando como reagente/solvente, sob refluxo por 16 horas, não apresentou distinção química entre os dois centros nucleofílicos em 1, os quais reagiram simultaneamente dando origem ao sistema heterocíclico inédito 3-metil-6-(5-metil-1,3,4-oxadiazol-2-il-[1,2,4]triazolo[4,3-a]piridina (5) com 82% de rendimento. A quimiodiferenciação de reatividade hidrazina-hidrazida favorecendo a função hidrazina foi observada quando 1 reagiu com aldeídos arílicos e heteroarílicos, em etanol, a 60 oC por 7 horas, resultando em uma série de sete novas 6-[2-aril/heteroarilmetilidenohidrazinil]nicotinohidrazidas (7) com rendimentos de 64 94%. Subsequentemente reações de ciclocondensação do tipo [3+2] envolvendo a função hidrazida livre de 7 e 4-alcóxi-4-alquil(aril/heteroaril)-1,1,1-triflúor-3-alquen-2-onas (8) resultou em uma nova série de nove 5-[(3-alquil/aril/heteroaril-5-trifluormetil-5-hidróxi-4,5-diidro-1H-pirazol-1-il]carbonilpiridin-2-il]aril/heteroarilideno hidrazonas (9) com 45 74% de rendimento. Exemplificando a possibilidade de obtenção de outros heterociclos utilizou-se como precursores a 6-[2-(4-clorobenzilideno)hidrazinil]nicotinohidrazida, que apresenta a função hidrazida livre, e ortoacetato de trietila. Desta forma, a oxadiazolil-piridina (10) (2-[5-(5-metil-1,3,4-oxadiazol-2-il)piridina-2-il]-4-clorobenzilideno hidrazona) foi obtida com 64% de rendimento quando a reação foi realizada sob refluxo durante 16 horas. Finalmente e com a intenção de demonstrar ainda a possibilidade de incorporação do metaloceno ferroceno no sistema heterocíclico em estudo, foram sintetizadas duas 6-[2-ferrocenilmetil(etil)idenohidrazinil]nicotinohidrazidas (12) com rendimentos de 58 72% e uma série derivada de seis 5-[(3-alquil/aril/heteroaril-5-trifluormetil-5-hidróxi-4,5-diidro-1H-pirazol-1-il)carbonilpiridin-2-il](ferrocenocarbo-xaldeído/acetilferroceno)hidrazonas (13) com rendimentos de 58 72%. Os compostos foram caracterizados por Espectroscopia de RMN de 1H e 13C{1H}, Cromatografia Gasosa acoplada à Espectrometria de Massas (CG-EM), Cromatografia Líquida acoplada à Espectrometria de Massas (LC-ESI-MS/MS) e sua pureza determinada via Análise Elementar CHN.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaQuímicaHidrazonasHeterociclosHidróliseCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAHidazida 6-hidrazinonicotínica: síntese quimio e regiosseletiva de piridinohidrazonas, ácidos pirazolil-nicotínicos e heterociclos derivados6-Hydrazinonicotinic acid hydrazide: chemo and regioselective synthesis of pyridine-hydrazones, pyrazolyl-nicotinic acids and heterocyclic derivativesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Andrade, Leandro Helgueira dehttp://lattes.cnpq.br/3293354976354711Rodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Zanatta, Nilohttp://lattes.cnpq.br/0719465062354576http://lattes.cnpq.br/5251399901014566Paim, Gisele Rocha10060000000040030030030030030006c852ad-d805-43c3-99d6-93a6a86f507c5ba24abc-fbee-40c9-ad46-4fd9503cde91885d328f-3b13-4ab9-9fc4-ccce98bc26d2f0970438-aab7-4bbe-8d26-13140ae7303aa3caf96b-54e9-4f59-95af-1941d0bb0087info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALPAIM, GISELE ROCHA.pdfapplication/pdf6840815http://repositorio.ufsm.br/bitstream/1/4220/1/PAIM%2c%20GISELE%20ROCHA.pdfc931721df5a3fe1fc2804babf8301156MD51TEXTPAIM, GISELE ROCHA.pdf.txtPAIM, GISELE ROCHA.pdf.txtExtracted texttext/plain294910http://repositorio.ufsm.br/bitstream/1/4220/2/PAIM%2c%20GISELE%20ROCHA.pdf.txtda77950c094583d546faab3d611aa5c0MD52THUMBNAILPAIM, GISELE ROCHA.pdf.jpgPAIM, GISELE ROCHA.pdf.jpgIM Thumbnailimage/jpeg5378http://repositorio.ufsm.br/bitstream/1/4220/3/PAIM%2c%20GISELE%20ROCHA.pdf.jpg6a5cd697ab78b4f313b2f067252c7e55MD531/42202022-08-25 15:46:06.404oai:repositorio.ufsm.br:1/4220Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2022-08-25T18:46:06Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Hidazida 6-hidrazinonicotínica: síntese quimio e regiosseletiva de piridinohidrazonas, ácidos pirazolil-nicotínicos e heterociclos derivados |
dc.title.alternative.eng.fl_str_mv |
6-Hydrazinonicotinic acid hydrazide: chemo and regioselective synthesis of pyridine-hydrazones, pyrazolyl-nicotinic acids and heterocyclic derivatives |
title |
Hidazida 6-hidrazinonicotínica: síntese quimio e regiosseletiva de piridinohidrazonas, ácidos pirazolil-nicotínicos e heterociclos derivados |
spellingShingle |
Hidazida 6-hidrazinonicotínica: síntese quimio e regiosseletiva de piridinohidrazonas, ácidos pirazolil-nicotínicos e heterociclos derivados Paim, Gisele Rocha Química Hidrazonas Heterociclos Hidrólise CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Hidazida 6-hidrazinonicotínica: síntese quimio e regiosseletiva de piridinohidrazonas, ácidos pirazolil-nicotínicos e heterociclos derivados |
title_full |
Hidazida 6-hidrazinonicotínica: síntese quimio e regiosseletiva de piridinohidrazonas, ácidos pirazolil-nicotínicos e heterociclos derivados |
title_fullStr |
Hidazida 6-hidrazinonicotínica: síntese quimio e regiosseletiva de piridinohidrazonas, ácidos pirazolil-nicotínicos e heterociclos derivados |
title_full_unstemmed |
Hidazida 6-hidrazinonicotínica: síntese quimio e regiosseletiva de piridinohidrazonas, ácidos pirazolil-nicotínicos e heterociclos derivados |
title_sort |
Hidazida 6-hidrazinonicotínica: síntese quimio e regiosseletiva de piridinohidrazonas, ácidos pirazolil-nicotínicos e heterociclos derivados |
author |
Paim, Gisele Rocha |
author_facet |
Paim, Gisele Rocha |
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 |
Andrade, Leandro Helgueira de |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/3293354976354711 |
dc.contributor.referee2.fl_str_mv |
Rodrigues, Oscar Endrigo Dorneles |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/6536519955416085 |
dc.contributor.referee3.fl_str_mv |
Zanatta, Nilo |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5251399901014566 |
dc.contributor.author.fl_str_mv |
Paim, Gisele Rocha |
contributor_str_mv |
Bonacorso, Helio Gauze Andrade, Leandro Helgueira de Rodrigues, Oscar Endrigo Dorneles Zanatta, Nilo |
dc.subject.por.fl_str_mv |
Química Hidrazonas Heterociclos Hidrólise |
topic |
Química Hidrazonas Heterociclos Hidrólise CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The present research firstly describes the study of methods for the hydrolysis of amide bond [C(O)-N] in 2-(5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)-5-(5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl-1-carbonyl)pyridines (2), where alkyl = CH3, aryl = C6H5, 4-OCH3C6H4, 4,4 -BiPh and heteroaryl = fur-2-yl, previously synthesized, aiming at the synthesis of a series of five pyrazolyl-nicotinic acids (3), applying basic conditions (NaOH, EtOH/H2O, 100 oC, 20 h) and their five esters derivatives (4) through reactions of 3 with thionyl chloride and methanol. These compounds were successfully obtained and in pure form with yields of 70 95% for nicotinic acids and between 57 84% for the aforementioned esters. Secondly, the study of the reactivity of 6-hydrazinonicotinic acid hydrazide reagent was developed (1), which presents two different nucleophilic centers in its chemical structure: hydrazine and hydrazide. First, a cyclocondensation reaction of [4+1] type was conducted between 1 and the triethylorthoacetate. This ortho ester, acting as reagent / solvent under reflux for 16 hours, presented no chemical distinction between the two nucleophilic centers in 1, which simultaneously reacted, originating the novel heterocyclic system 3-methyl-6-(5-methyl -1,3,4-oxadiazol-2-yl-[1,2,4] triazolo[4,3-a]pyridine in 82% yield. The chemo-differentiation reactivity of the hydrazine-hydrazide moieties favoring hydrazine function was observed when 1 reacted with aryl and heteroaryl aldehydes in ethanol solvent at 60 °C for 7 hours, resulting in a series of seven new 6-[2-aryl/heteroarylmethylidenehydrazinyl]nicotinohydrazides (7) with 64 - 94% yields. Subsequently, the cyclocondensation reactions of [3 + 2] type involving the hydrazide 7 free function and the 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones (8) resulted in a new series of nine 5-[(3-alkyl(aryl/heteroaryl)-5- trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)carbonylpyridin-2-yl]aryl/ heteroarylaldehyde hydrazones (9) with 45 74% yields. Illustrating the possibility of obtaining other heterocycles, the 6-[2-aryl/heteroarylmethylidenehydrazinyl]nicotinohydrazides, which presents free hydrazide function, and triethylorthoacetate were used as predecessors. Therefore, the oxadiazolyl-pyridine (10) 2-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-pyridin-2-yl]-4-chlorobenzaldehyde hydrazone was obtained in 64% yield when this reaction was developed under reflux for 16 hours. Finally, with the intention of demonstrating the possibility of incorporating the metallocene ferrocene into the organic heterocyclic system under investigation, two 6-[2-ferrocenylmethyl(ethyl)idenehydrazino]nicotinic hydrazide (12) were synthesized with yields from 58 to 72% and a derived series from six 5-[(3-alkyl(aryl/heteroaryl)-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)carbonylpyridin-2-yl] acetylferrocene/ferrocenecarboxaldehyde hydrazones (13) with yields from 58 to 72%. The compounds were characterized by 1H and 13C {1H} NMR Spectroscopy, Gas Chromatography coupled to Mass Spectrometry (GC-MS), Liquid Chromatography coupled to Mass Spectrometry (LC-ESI-MS/MS) and their purity determined by CHN Elemental Analysis. |
publishDate |
2012 |
dc.date.issued.fl_str_mv |
2012-04-20 |
dc.date.accessioned.fl_str_mv |
2017-05-16 |
dc.date.available.fl_str_mv |
2017-05-16 |
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 |
PAIM, Gisele Rocha. 6-Hydrazinonicotinic acid hydrazide: chemo and regioselective synthesis of pyridine-hydrazones, pyrazolyl-nicotinic acids and heterocyclic derivatives. 2012. 253 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2012. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/4220 |
identifier_str_mv |
PAIM, Gisele Rocha. 6-Hydrazinonicotinic acid hydrazide: chemo and regioselective synthesis of pyridine-hydrazones, pyrazolyl-nicotinic acids and heterocyclic derivatives. 2012. 253 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2012. |
url |
http://repositorio.ufsm.br/handle/1/4220 |
dc.language.iso.fl_str_mv |
por |
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por |
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100600000000 |
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openAccess |
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Universidade Federal de Santa Maria |
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Programa de Pós-Graduação em Química |
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UFSM |
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Química |
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Universidade Federal de Santa Maria |
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