A straightforward and efficient method for the synthesis of diversely substituted β-aminoketones and γ-aminoalcohols from 3-(N,N-dimethylamino)propiophenones as starting materials

Detalhes bibliográficos
Autor(a) principal: Abonia,Rodrigo
Data de Publicação: 2013
Outros Autores: Arteaga,Danny, Castillo,Juan, Insuasty,Braulio, Quiroga,Jairo, Ortíz,Alejandro
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=S0103-50532013000900002
Resumo: Libraries of novel β-aminoketones and γ-aminoalcohols showing a wide structural diversity were easily obtained from a simple approach, using 3-(N,N-dimethylamino)propiophenone derivatives as key starting material. The procedure involved initially an N-alkylation of secondary benzylamines with propiophenone salts yielding the desired β-aminoketones. Chemical or catalytic reduction of their carbonyl groups provided the final γ-aminoalcohols in good yields. This protocol proved to be convenient as an alternative route for the synthesis of the local anesthetic Falicain® and for the topic antifungal drug Naftifine®.
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spelling A straightforward and efficient method for the synthesis of diversely substituted β-aminoketones and γ-aminoalcohols from 3-(N,N-dimethylamino)propiophenones as starting materialsbenzylaminespropiophenonesβ-aminoketonesγ-aminoalcoholsMannich type reactionLibraries of novel β-aminoketones and γ-aminoalcohols showing a wide structural diversity were easily obtained from a simple approach, using 3-(N,N-dimethylamino)propiophenone derivatives as key starting material. The procedure involved initially an N-alkylation of secondary benzylamines with propiophenone salts yielding the desired β-aminoketones. Chemical or catalytic reduction of their carbonyl groups provided the final γ-aminoalcohols in good yields. This protocol proved to be convenient as an alternative route for the synthesis of the local anesthetic Falicain® and for the topic antifungal drug Naftifine®.Sociedade Brasileira de Química2013-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000900002Journal of the Brazilian Chemical Society v.24 n.9 2013reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20130177info:eu-repo/semantics/openAccessAbonia,RodrigoArteaga,DannyCastillo,JuanInsuasty,BraulioQuiroga,JairoOrtíz,Alejandroeng2013-09-24T00:00:00Zoai:scielo:S0103-50532013000900002Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2013-09-24T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv A straightforward and efficient method for the synthesis of diversely substituted β-aminoketones and γ-aminoalcohols from 3-(N,N-dimethylamino)propiophenones as starting materials
title A straightforward and efficient method for the synthesis of diversely substituted β-aminoketones and γ-aminoalcohols from 3-(N,N-dimethylamino)propiophenones as starting materials
spellingShingle A straightforward and efficient method for the synthesis of diversely substituted β-aminoketones and γ-aminoalcohols from 3-(N,N-dimethylamino)propiophenones as starting materials
Abonia,Rodrigo
benzylamines
propiophenones
β-aminoketones
γ-aminoalcohols
Mannich type reaction
title_short A straightforward and efficient method for the synthesis of diversely substituted β-aminoketones and γ-aminoalcohols from 3-(N,N-dimethylamino)propiophenones as starting materials
title_full A straightforward and efficient method for the synthesis of diversely substituted β-aminoketones and γ-aminoalcohols from 3-(N,N-dimethylamino)propiophenones as starting materials
title_fullStr A straightforward and efficient method for the synthesis of diversely substituted β-aminoketones and γ-aminoalcohols from 3-(N,N-dimethylamino)propiophenones as starting materials
title_full_unstemmed A straightforward and efficient method for the synthesis of diversely substituted β-aminoketones and γ-aminoalcohols from 3-(N,N-dimethylamino)propiophenones as starting materials
title_sort A straightforward and efficient method for the synthesis of diversely substituted β-aminoketones and γ-aminoalcohols from 3-(N,N-dimethylamino)propiophenones as starting materials
author Abonia,Rodrigo
author_facet Abonia,Rodrigo
Arteaga,Danny
Castillo,Juan
Insuasty,Braulio
Quiroga,Jairo
Ortíz,Alejandro
author_role author
author2 Arteaga,Danny
Castillo,Juan
Insuasty,Braulio
Quiroga,Jairo
Ortíz,Alejandro
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Abonia,Rodrigo
Arteaga,Danny
Castillo,Juan
Insuasty,Braulio
Quiroga,Jairo
Ortíz,Alejandro
dc.subject.por.fl_str_mv benzylamines
propiophenones
β-aminoketones
γ-aminoalcohols
Mannich type reaction
topic benzylamines
propiophenones
β-aminoketones
γ-aminoalcohols
Mannich type reaction
description Libraries of novel β-aminoketones and γ-aminoalcohols showing a wide structural diversity were easily obtained from a simple approach, using 3-(N,N-dimethylamino)propiophenone derivatives as key starting material. The procedure involved initially an N-alkylation of secondary benzylamines with propiophenone salts yielding the desired β-aminoketones. Chemical or catalytic reduction of their carbonyl groups provided the final γ-aminoalcohols in good yields. This protocol proved to be convenient as an alternative route for the synthesis of the local anesthetic Falicain® and for the topic antifungal drug Naftifine®.
publishDate 2013
dc.date.none.fl_str_mv 2013-09-01
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=S0103-50532013000900002
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000900002
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20130177
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.24 n.9 2013
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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