Síntese de 1h-1,2,3-triazol-4-il-1,3,4-oxadiazóis a partir de 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas
Autor(a) principal: | |
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Data de Publicação: | 2014 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional Manancial UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/10593 |
Resumo: | This work describes the synthesis and the characterization of series of substituted trichloroacetyl 1H-1,2,3-triazoles (10 12), 1H-1,2,3-triazol-4-yl-carbohydrazides (14 16) and 1H-1,2,3-triazol-4-yl-1,3,4-oxadiazoles (18 19), obtained through a synthetic route that contains three reactions steps, having as the initial step, the reaction of 1,3-dipolar cycloaddition between 4-alcoxy-1,1,1-trichloro-3-alken-2-ones (1a,b) and substituted benzyl azides (7 9), like a intermediate step, the haloform reaction between substituted trichloroacetyl 1H-1,2,3-triazoles (10 12) and hydrazine monohydrate (13), and as the final step, the cycloaddition reaction type [4 + 1] between 1H-1,2,3-triazol-4-yl-carbohydrazides (14 16) and triethyl orthoacetate (17). Two 4-alcoxy-l-1,1,1-trichloro-3-alken-2-ones (1a,b) and three substituted benzyl azides (7 9) were employed in the synthesis of substituted trichloroacetyl 1H-1,2,3-triazoles (10 12), resulting in six compounds with yields of 40 to 75 %, all of them having, strategically, the trichloroacetyl substituent in the position 4 of the triazolic ring. Posteriorly, this triazoles (10 12) carried the obtaining of five examples of 1H-1,2,3-triazol-4-yl-carbohydrazides (14 16) through the reactions front hydrazine monohydrate (13), with yields of 73 to 82 %. Finally, the carbohydrazides (14 16) and the triethyl orthoacetate (17) were employed to obtaining of 1H-1,2,3-triazol-4-yl-1,3,4-oxadiazoles (18 19 ), with yields of 65 to 71 %, however, the compound 1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl-carbohydrazide (16) carried the obtaining of a carbazone N -(1-ethoxyethylene)-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]hydrazine (20), with yields of 48 %. The most of this compounds obtained (11 examples) are unpublished. Proving the synthetic versatility of carbohydrazides, the compounds 1-(2,6-difluorobenzyl)-1H-1,2,3-triazol-4-yl-carbohydrazide (14a) and 1,1,1-trifluoro-4- Dissertação de Mestrado Fábio Mulazzani da Luz - 2014 methoxy-4-phenyl-but-3-en-2-one (2) were employed in the synthesis of one example of pyrazolinyltriazolylketone (21), get with a yield of 70 %. This compound is also unpublished. The structural analysis of the compounds were characterized for experiments of 1H, 13C, and mass spectrometry (CG-MS), and them purity determined by elemental analysis. |
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2017-05-152017-05-152014-09-12LUZ, Fábio Mulazzani da. Synthesis of 1h-1,2,3-triazol-4-il-1,3,4-oxadiazoles from 4-alcoxy-1,1,1-trichloro-3-alken-2-ones. 2014. 187 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2014.http://repositorio.ufsm.br/handle/1/10593This work describes the synthesis and the characterization of series of substituted trichloroacetyl 1H-1,2,3-triazoles (10 12), 1H-1,2,3-triazol-4-yl-carbohydrazides (14 16) and 1H-1,2,3-triazol-4-yl-1,3,4-oxadiazoles (18 19), obtained through a synthetic route that contains three reactions steps, having as the initial step, the reaction of 1,3-dipolar cycloaddition between 4-alcoxy-1,1,1-trichloro-3-alken-2-ones (1a,b) and substituted benzyl azides (7 9), like a intermediate step, the haloform reaction between substituted trichloroacetyl 1H-1,2,3-triazoles (10 12) and hydrazine monohydrate (13), and as the final step, the cycloaddition reaction type [4 + 1] between 1H-1,2,3-triazol-4-yl-carbohydrazides (14 16) and triethyl orthoacetate (17). Two 4-alcoxy-l-1,1,1-trichloro-3-alken-2-ones (1a,b) and three substituted benzyl azides (7 9) were employed in the synthesis of substituted trichloroacetyl 1H-1,2,3-triazoles (10 12), resulting in six compounds with yields of 40 to 75 %, all of them having, strategically, the trichloroacetyl substituent in the position 4 of the triazolic ring. Posteriorly, this triazoles (10 12) carried the obtaining of five examples of 1H-1,2,3-triazol-4-yl-carbohydrazides (14 16) through the reactions front hydrazine monohydrate (13), with yields of 73 to 82 %. Finally, the carbohydrazides (14 16) and the triethyl orthoacetate (17) were employed to obtaining of 1H-1,2,3-triazol-4-yl-1,3,4-oxadiazoles (18 19 ), with yields of 65 to 71 %, however, the compound 1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl-carbohydrazide (16) carried the obtaining of a carbazone N -(1-ethoxyethylene)-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]hydrazine (20), with yields of 48 %. The most of this compounds obtained (11 examples) are unpublished. Proving the synthetic versatility of carbohydrazides, the compounds 1-(2,6-difluorobenzyl)-1H-1,2,3-triazol-4-yl-carbohydrazide (14a) and 1,1,1-trifluoro-4- Dissertação de Mestrado Fábio Mulazzani da Luz - 2014 methoxy-4-phenyl-but-3-en-2-one (2) were employed in the synthesis of one example of pyrazolinyltriazolylketone (21), get with a yield of 70 %. This compound is also unpublished. The structural analysis of the compounds were characterized for experiments of 1H, 13C, and mass spectrometry (CG-MS), and them purity determined by elemental analysis.Este trabalho descreve a síntese e a caracterização de séries de 1H-1,2,3-triazóis tricloroacetil substituídos (10 12), 1H-1,2,3-triazol-4-il-carboidrazidas (14 16) e 1H-1,2,3-triazol-4-il-1,3,4-oxadiazóis (18 19), obtidos através de um rota sintética que contém três passos reacionais, tendo como passo inicial, a reação de cicloadição 1,3-dipolar entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas (1a,b) e benzil azidas substituídas (7 9), como passo intermediário a reação halofórmica entre 1H-1,2,3-triazóis tricloroacetil substituídos (10 12) e hidrazina monoidratada (13), e como passo final a reação de ciclocondensação [4 + 1] entre 1H-1,2,3-triazol-4-il-carboidrazidas (14 16) e ortoacetato de trietila (17). Duas 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas (1a,b) e três benzil azidas substituídas (7 9) foram empregadas na síntese 1H-1,2,3-triazol tricloroacetil substituídos (10 12), que resultou em seis compostos com rendimentos de 40 a 75 %, todos contendo, estrategicamente, o substituinte tricloroacetila na posição 4 do anel triazólico. Posteriormente estes triazóis (10 12) levaram a obteção de cinco exemplos de 1H-1,2,3-triazol-4-il-carboidrazidas (14 16) através da reação frente hidrazina monoidratada (13), com rendimentos de 73 a 82 %. Por fim, as carboidrazidas (14 16) e o ortoacetato de trietila (17) foram empregados para a obtenção de 1H-1,2,3-triazol-4-il-1,3,4-oxadiazóis (18 19), com rendimentos de 65 a 71 %, entretanto, o composto 1-(4-metoxibenzil)-1H-1,2,3-triazol-4-il-carboidrazida (16) levou à obtenção da carbazona N -(1-etoxietileno)-[1-(4-metoxibenzil)-1H-1,2,3-triazol-4-il]hidrazida (20), com rendimento de 48 %. A grande maioria destes compostos obtidos (11 exemplos) são inéditos. Para provar a versatilidade sintética de carboidrazidas, os compostos 1-(2,6-difluorbenzil)-1H-1,2,3-triazol-4-il-carboidrazida (14a) e 4-fenil-1,1,1-triflúor-4-metóxi-but-3-en-2-ona (2) foram empregados na síntese de um exemplo de Dissertação de Mestrado Fábio Mulazzani da Luz - 2014 pirazoliniltriazolilcetona (21), obtido com um rendimento de 70 %. Composto também inédito. A análise estrutural dos compostos sintetizados foi caracterizada por experimentos de RMN de 1H, 13C, e espectrometria de massas (GC-EM), e sua pureza determinada via análise elementar.application/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaTriazoisQuímicaHeterociclosCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 1h-1,2,3-triazol-4-il-1,3,4-oxadiazóis a partir de 4-alcóxi-1,1,1-tricloro-3-alquen-2-onasSynthesis of 1h-1,2,3-triazol-4-il-1,3,4-oxadiazoles from 4-alcoxy-1,1,1-trichloro-3-alken-2-onesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0Dalcol, Ionara Irionhttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797864E9Severo Filho, Wolmar Alípiohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4790001P6http://lattes.cnpq.br/0046468189169307Luz, Fábio Mulazzani da10060000000040050030050050006c852ad-d805-43c3-99d6-93a6a86f507c0b27f8af-dd3f-4586-ba70-dd16aa1b15452cbacb00-be94-498b-9c77-1d47963baf69a07c475c-60f3-4ff9-bff8-2a4f54329a61info:eu-repo/semantics/openAccessreponame:Repositório Institucional Manancial UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALLUZ, FABIO MULAZZANI DA.pdfapplication/pdf2652585http://repositorio.ufsm.br/bitstream/1/10593/1/LUZ%2c%20FABIO%20MULAZZANI%20DA.pdfb0837d7c5a04cceb90e184476d1d2436MD51TEXTLUZ, FABIO MULAZZANI DA.pdf.txtLUZ, FABIO MULAZZANI DA.pdf.txtExtracted texttext/plain224385http://repositorio.ufsm.br/bitstream/1/10593/2/LUZ%2c%20FABIO%20MULAZZANI%20DA.pdf.txtc6d091db0dcc4fd83c3aa5f6bed0dfa0MD52THUMBNAILLUZ, FABIO MULAZZANI DA.pdf.jpgLUZ, FABIO MULAZZANI DA.pdf.jpgIM Thumbnailimage/jpeg5727http://repositorio.ufsm.br/bitstream/1/10593/3/LUZ%2c%20FABIO%20MULAZZANI%20DA.pdf.jpg6e80e0483b8bfaf0663f086375e273beMD531/105932022-08-29 11:15:27.412oai:repositorio.ufsm.br:1/10593Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestouvidoria@ufsm.bropendoar:39132022-08-29T14:15:27Repositório Institucional Manancial UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de 1h-1,2,3-triazol-4-il-1,3,4-oxadiazóis a partir de 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 1h-1,2,3-triazol-4-il-1,3,4-oxadiazoles from 4-alcoxy-1,1,1-trichloro-3-alken-2-ones |
title |
Síntese de 1h-1,2,3-triazol-4-il-1,3,4-oxadiazóis a partir de 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas |
spellingShingle |
Síntese de 1h-1,2,3-triazol-4-il-1,3,4-oxadiazóis a partir de 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas Luz, Fábio Mulazzani da Triazois Química Heterociclos CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 1h-1,2,3-triazol-4-il-1,3,4-oxadiazóis a partir de 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas |
title_full |
Síntese de 1h-1,2,3-triazol-4-il-1,3,4-oxadiazóis a partir de 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas |
title_fullStr |
Síntese de 1h-1,2,3-triazol-4-il-1,3,4-oxadiazóis a partir de 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas |
title_full_unstemmed |
Síntese de 1h-1,2,3-triazol-4-il-1,3,4-oxadiazóis a partir de 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas |
title_sort |
Síntese de 1h-1,2,3-triazol-4-il-1,3,4-oxadiazóis a partir de 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas |
author |
Luz, Fábio Mulazzani da |
author_facet |
Luz, Fábio Mulazzani da |
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 |
Dalcol, Ionara Irion |
dc.contributor.referee1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797864E9 |
dc.contributor.referee2.fl_str_mv |
Severo Filho, Wolmar Alípio |
dc.contributor.referee2Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4790001P6 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0046468189169307 |
dc.contributor.author.fl_str_mv |
Luz, Fábio Mulazzani da |
contributor_str_mv |
Bonacorso, Helio Gauze Dalcol, Ionara Irion Severo Filho, Wolmar Alípio |
dc.subject.por.fl_str_mv |
Triazois Química Heterociclos |
topic |
Triazois Química Heterociclos 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 synthesis and the characterization of series of substituted trichloroacetyl 1H-1,2,3-triazoles (10 12), 1H-1,2,3-triazol-4-yl-carbohydrazides (14 16) and 1H-1,2,3-triazol-4-yl-1,3,4-oxadiazoles (18 19), obtained through a synthetic route that contains three reactions steps, having as the initial step, the reaction of 1,3-dipolar cycloaddition between 4-alcoxy-1,1,1-trichloro-3-alken-2-ones (1a,b) and substituted benzyl azides (7 9), like a intermediate step, the haloform reaction between substituted trichloroacetyl 1H-1,2,3-triazoles (10 12) and hydrazine monohydrate (13), and as the final step, the cycloaddition reaction type [4 + 1] between 1H-1,2,3-triazol-4-yl-carbohydrazides (14 16) and triethyl orthoacetate (17). Two 4-alcoxy-l-1,1,1-trichloro-3-alken-2-ones (1a,b) and three substituted benzyl azides (7 9) were employed in the synthesis of substituted trichloroacetyl 1H-1,2,3-triazoles (10 12), resulting in six compounds with yields of 40 to 75 %, all of them having, strategically, the trichloroacetyl substituent in the position 4 of the triazolic ring. Posteriorly, this triazoles (10 12) carried the obtaining of five examples of 1H-1,2,3-triazol-4-yl-carbohydrazides (14 16) through the reactions front hydrazine monohydrate (13), with yields of 73 to 82 %. Finally, the carbohydrazides (14 16) and the triethyl orthoacetate (17) were employed to obtaining of 1H-1,2,3-triazol-4-yl-1,3,4-oxadiazoles (18 19 ), with yields of 65 to 71 %, however, the compound 1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl-carbohydrazide (16) carried the obtaining of a carbazone N -(1-ethoxyethylene)-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]hydrazine (20), with yields of 48 %. The most of this compounds obtained (11 examples) are unpublished. Proving the synthetic versatility of carbohydrazides, the compounds 1-(2,6-difluorobenzyl)-1H-1,2,3-triazol-4-yl-carbohydrazide (14a) and 1,1,1-trifluoro-4- Dissertação de Mestrado Fábio Mulazzani da Luz - 2014 methoxy-4-phenyl-but-3-en-2-one (2) were employed in the synthesis of one example of pyrazolinyltriazolylketone (21), get with a yield of 70 %. This compound is also unpublished. The structural analysis of the compounds were characterized for experiments of 1H, 13C, and mass spectrometry (CG-MS), and them purity determined by elemental analysis. |
publishDate |
2014 |
dc.date.issued.fl_str_mv |
2014-09-12 |
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2017-05-15 |
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2017-05-15 |
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info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
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masterThesis |
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publishedVersion |
dc.identifier.citation.fl_str_mv |
LUZ, Fábio Mulazzani da. Synthesis of 1h-1,2,3-triazol-4-il-1,3,4-oxadiazoles from 4-alcoxy-1,1,1-trichloro-3-alken-2-ones. 2014. 187 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2014. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10593 |
identifier_str_mv |
LUZ, Fábio Mulazzani da. Synthesis of 1h-1,2,3-triazol-4-il-1,3,4-oxadiazoles from 4-alcoxy-1,1,1-trichloro-3-alken-2-ones. 2014. 187 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2014. |
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http://repositorio.ufsm.br/handle/1/10593 |
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