Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through fatorial design

Detalhes bibliográficos
Autor(a) principal: Fernandes,João Paulo dos Santos
Data de Publicação: 2009
Outros Autores: Felli,Veni Maria Andres
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Química Nova (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422009000900040
Resumo: Pyrazinoic acid esters have been synthesized as prodrugs of pyrazinoic acid. In the literature, its preparation is reported through the reaction of pyrazinoyl chloride with alcohols and the reaction with DCC/DMAP. In this work, it is reported a 2² factorial design to evaluate the preparation of these esters through the substitution of alkyl bromides with carboxylate anion. The controlled factors were alkyl chain length of bromides (ethyl and hexyl) and the used base (triethylamine and DBU). Results revealed that the used base used has significant effect on yield, and alkyl bromide used has neither significant influence, nor its interaction effect with base.
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spelling Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through fatorial designesterificationantimycobacterial agentfactorial designPyrazinoic acid esters have been synthesized as prodrugs of pyrazinoic acid. In the literature, its preparation is reported through the reaction of pyrazinoyl chloride with alcohols and the reaction with DCC/DMAP. In this work, it is reported a 2² factorial design to evaluate the preparation of these esters through the substitution of alkyl bromides with carboxylate anion. The controlled factors were alkyl chain length of bromides (ethyl and hexyl) and the used base (triethylamine and DBU). Results revealed that the used base used has significant effect on yield, and alkyl bromide used has neither significant influence, nor its interaction effect with base.Sociedade Brasileira de Química2009-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422009000900040Química Nova v.32 n.9 2009reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0100-40422009000900040info:eu-repo/semantics/openAccessFernandes,João Paulo dos SantosFelli,Veni Maria Andreseng2010-01-06T00:00:00Zoai:scielo:S0100-40422009000900040Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2010-01-06T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through fatorial design
title Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through fatorial design
spellingShingle Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through fatorial design
Fernandes,João Paulo dos Santos
esterification
antimycobacterial agent
factorial design
title_short Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through fatorial design
title_full Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through fatorial design
title_fullStr Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through fatorial design
title_full_unstemmed Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through fatorial design
title_sort Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through fatorial design
author Fernandes,João Paulo dos Santos
author_facet Fernandes,João Paulo dos Santos
Felli,Veni Maria Andres
author_role author
author2 Felli,Veni Maria Andres
author2_role author
dc.contributor.author.fl_str_mv Fernandes,João Paulo dos Santos
Felli,Veni Maria Andres
dc.subject.por.fl_str_mv esterification
antimycobacterial agent
factorial design
topic esterification
antimycobacterial agent
factorial design
description Pyrazinoic acid esters have been synthesized as prodrugs of pyrazinoic acid. In the literature, its preparation is reported through the reaction of pyrazinoyl chloride with alcohols and the reaction with DCC/DMAP. In this work, it is reported a 2² factorial design to evaluate the preparation of these esters through the substitution of alkyl bromides with carboxylate anion. The controlled factors were alkyl chain length of bromides (ethyl and hexyl) and the used base (triethylamine and DBU). Results revealed that the used base used has significant effect on yield, and alkyl bromide used has neither significant influence, nor its interaction effect with base.
publishDate 2009
dc.date.none.fl_str_mv 2009-01-01
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=S0100-40422009000900040
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422009000900040
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0100-40422009000900040
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 Química Nova v.32 n.9 2009
reponame:Química Nova (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Química Nova (Online)
collection Química Nova (Online)
repository.name.fl_str_mv Química Nova (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv quimicanova@sbq.org.br
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