Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Bases

Detalhes bibliográficos
Autor(a) principal: Aouad,Mohamed R.
Data de Publicação: 2015
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015001002105
Resumo: A facile and convenient green click synthesis has been developed for the preparation of new fluorinated 1,2,3-triazoles under solvent-free conditions via a Huisgen 1,3-dipolar cycloaddition reaction between dimethylacetylene dicarboxylate (DMADC) and fluorophenyl azides in excellent yields within 2 min. Treatment of the resulting diesters with hydrazine hydrate furnished the corresponding dihydrazides, which, upon condensation with benzaldehyde derivatives, afforded a new series of bis-hydrazones. All of the synthesized compounds were fully characterized using infrared (IR) spectroscopy, 1H, 13C and 19F nuclear magnetic resonance (NMR), mass spectrometry (MS) and elemental analysis. A preliminary bioassay indicated that some of the tested compounds exhibited significant antimicrobial activity.
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spelling Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Basesfree solvent reactionclick synthesis1,2,3-triazolesSchiff basesantimicrobial activityA facile and convenient green click synthesis has been developed for the preparation of new fluorinated 1,2,3-triazoles under solvent-free conditions via a Huisgen 1,3-dipolar cycloaddition reaction between dimethylacetylene dicarboxylate (DMADC) and fluorophenyl azides in excellent yields within 2 min. Treatment of the resulting diesters with hydrazine hydrate furnished the corresponding dihydrazides, which, upon condensation with benzaldehyde derivatives, afforded a new series of bis-hydrazones. All of the synthesized compounds were fully characterized using infrared (IR) spectroscopy, 1H, 13C and 19F nuclear magnetic resonance (NMR), mass spectrometry (MS) and elemental analysis. A preliminary bioassay indicated that some of the tested compounds exhibited significant antimicrobial activity.Sociedade Brasileira de Química2015-10-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015001002105Journal of the Brazilian Chemical Society v.26 n.10 2015reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20150196info:eu-repo/semantics/openAccessAouad,Mohamed R.eng2015-10-22T00:00:00Zoai:scielo:S0103-50532015001002105Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2015-10-22T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Bases
title Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Bases
spellingShingle Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Bases
Aouad,Mohamed R.
free solvent reaction
click synthesis
1,2,3-triazoles
Schiff bases
antimicrobial activity
title_short Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Bases
title_full Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Bases
title_fullStr Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Bases
title_full_unstemmed Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Bases
title_sort Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Bases
author Aouad,Mohamed R.
author_facet Aouad,Mohamed R.
author_role author
dc.contributor.author.fl_str_mv Aouad,Mohamed R.
dc.subject.por.fl_str_mv free solvent reaction
click synthesis
1,2,3-triazoles
Schiff bases
antimicrobial activity
topic free solvent reaction
click synthesis
1,2,3-triazoles
Schiff bases
antimicrobial activity
description A facile and convenient green click synthesis has been developed for the preparation of new fluorinated 1,2,3-triazoles under solvent-free conditions via a Huisgen 1,3-dipolar cycloaddition reaction between dimethylacetylene dicarboxylate (DMADC) and fluorophenyl azides in excellent yields within 2 min. Treatment of the resulting diesters with hydrazine hydrate furnished the corresponding dihydrazides, which, upon condensation with benzaldehyde derivatives, afforded a new series of bis-hydrazones. All of the synthesized compounds were fully characterized using infrared (IR) spectroscopy, 1H, 13C and 19F nuclear magnetic resonance (NMR), mass spectrometry (MS) and elemental analysis. A preliminary bioassay indicated that some of the tested compounds exhibited significant antimicrobial activity.
publishDate 2015
dc.date.none.fl_str_mv 2015-10-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015001002105
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015001002105
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20150196
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.26 n.10 2015
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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