Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: experimental and theoretical study of their physicochemical properties using DFT calculations

Detalhes bibliográficos
Autor(a) principal: Mirjafary,Zohreh
Data de Publicação: 2014
Outros Autores: Saidian,Hamid, Sahandi,Morteza, Shojaei,Leila
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=S0103-50532014000700014
Resumo: A convenient reaction of 2-chloroquinoline-3-carbaldehyde derivatives and dimedone in the presence of KF-Al2O3 for the synthesis of useful pyranoquinolines is described. Reasonable yields (41-50%), easily available starting materials and less expensive efficient catalyst are the key features of the present method. A mechanism was proposed for the reaction course. Attribution of the chemical shifts was made with the help of the density functional theory (DFT) calculations. The computed nuclear magnetic resonance (NMR) chemical shifts are in good agreement with available experimental data. The nucleus-independent chemical shift (NICS) values were used as quantitative measures for the relative aromatic character in pyranoquinolines. The calculated NICS values obtained for the phenyl group of pyranoquinoline compounds are smaller than that of benzene.
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spelling Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: experimental and theoretical study of their physicochemical properties using DFT calculationsquinolinepyranoquinolineKnoevenagel condensationaromaticityDFT calculationsA convenient reaction of 2-chloroquinoline-3-carbaldehyde derivatives and dimedone in the presence of KF-Al2O3 for the synthesis of useful pyranoquinolines is described. Reasonable yields (41-50%), easily available starting materials and less expensive efficient catalyst are the key features of the present method. A mechanism was proposed for the reaction course. Attribution of the chemical shifts was made with the help of the density functional theory (DFT) calculations. The computed nuclear magnetic resonance (NMR) chemical shifts are in good agreement with available experimental data. The nucleus-independent chemical shift (NICS) values were used as quantitative measures for the relative aromatic character in pyranoquinolines. The calculated NICS values obtained for the phenyl group of pyranoquinoline compounds are smaller than that of benzene.Sociedade Brasileira de Química2014-07-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532014000700014Journal of the Brazilian Chemical Society v.25 n.7 2014reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20140103info:eu-repo/semantics/openAccessMirjafary,ZohrehSaidian,HamidSahandi,MortezaShojaei,Leilaeng2014-07-17T00:00:00Zoai:scielo:S0103-50532014000700014Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2014-07-17T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: experimental and theoretical study of their physicochemical properties using DFT calculations
title Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: experimental and theoretical study of their physicochemical properties using DFT calculations
spellingShingle Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: experimental and theoretical study of their physicochemical properties using DFT calculations
Mirjafary,Zohreh
quinoline
pyranoquinoline
Knoevenagel condensation
aromaticity
DFT calculations
title_short Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: experimental and theoretical study of their physicochemical properties using DFT calculations
title_full Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: experimental and theoretical study of their physicochemical properties using DFT calculations
title_fullStr Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: experimental and theoretical study of their physicochemical properties using DFT calculations
title_full_unstemmed Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: experimental and theoretical study of their physicochemical properties using DFT calculations
title_sort Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: experimental and theoretical study of their physicochemical properties using DFT calculations
author Mirjafary,Zohreh
author_facet Mirjafary,Zohreh
Saidian,Hamid
Sahandi,Morteza
Shojaei,Leila
author_role author
author2 Saidian,Hamid
Sahandi,Morteza
Shojaei,Leila
author2_role author
author
author
dc.contributor.author.fl_str_mv Mirjafary,Zohreh
Saidian,Hamid
Sahandi,Morteza
Shojaei,Leila
dc.subject.por.fl_str_mv quinoline
pyranoquinoline
Knoevenagel condensation
aromaticity
DFT calculations
topic quinoline
pyranoquinoline
Knoevenagel condensation
aromaticity
DFT calculations
description A convenient reaction of 2-chloroquinoline-3-carbaldehyde derivatives and dimedone in the presence of KF-Al2O3 for the synthesis of useful pyranoquinolines is described. Reasonable yields (41-50%), easily available starting materials and less expensive efficient catalyst are the key features of the present method. A mechanism was proposed for the reaction course. Attribution of the chemical shifts was made with the help of the density functional theory (DFT) calculations. The computed nuclear magnetic resonance (NMR) chemical shifts are in good agreement with available experimental data. The nucleus-independent chemical shift (NICS) values were used as quantitative measures for the relative aromatic character in pyranoquinolines. The calculated NICS values obtained for the phenyl group of pyranoquinoline compounds are smaller than that of benzene.
publishDate 2014
dc.date.none.fl_str_mv 2014-07-01
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=S0103-50532014000700014
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532014000700014
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20140103
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.25 n.7 2014
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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