Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA

Detalhes bibliográficos
Autor(a) principal: Rosa,Flávia A. F. da
Data de Publicação: 2003
Outros Autores: Rebelo,Ricardo A., Nascimento,Maria G.
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=S0103-50532003000100003
Resumo: The synthesis of 5,6-methylenedioxy-indol-3-yl-methanoic acid 8 and 5,6-methylenedioxy-indol-3-yl-acetic acid 13 is described. Piperonal was employed as starting material, and the construction of the heterocyclic ring based on the Hemetsberger reaction of the corresponding beta-azidostyrene was highly regiospecific. Compound 8 was obtained as a key intermediate towards 13, and a Mannich reaction was used to introduce the required alkyl side chain. The route comprised eight steps giving 13 in 26% overall yield. The formation of the indolic ring via reductive cyclisation of o,beta-dinitrostyrene is also presented.
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spelling Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAAindolecarboxylic acidsnitrene insertionpiperonalplant growth regulatorThe synthesis of 5,6-methylenedioxy-indol-3-yl-methanoic acid 8 and 5,6-methylenedioxy-indol-3-yl-acetic acid 13 is described. Piperonal was employed as starting material, and the construction of the heterocyclic ring based on the Hemetsberger reaction of the corresponding beta-azidostyrene was highly regiospecific. Compound 8 was obtained as a key intermediate towards 13, and a Mannich reaction was used to introduce the required alkyl side chain. The route comprised eight steps giving 13 in 26% overall yield. The formation of the indolic ring via reductive cyclisation of o,beta-dinitrostyrene is also presented.Sociedade Brasileira de Química2003-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000100003Journal of the Brazilian Chemical Society v.14 n.1 2003reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532003000100003info:eu-repo/semantics/openAccessRosa,Flávia A. F. daRebelo,Ricardo A.Nascimento,Maria G.eng2003-04-07T00:00:00Zoai:scielo:S0103-50532003000100003Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2003-04-07T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA
title Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA
spellingShingle Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA
Rosa,Flávia A. F. da
indolecarboxylic acids
nitrene insertion
piperonal
plant growth regulator
title_short Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA
title_full Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA
title_fullStr Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA
title_full_unstemmed Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA
title_sort Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA
author Rosa,Flávia A. F. da
author_facet Rosa,Flávia A. F. da
Rebelo,Ricardo A.
Nascimento,Maria G.
author_role author
author2 Rebelo,Ricardo A.
Nascimento,Maria G.
author2_role author
author
dc.contributor.author.fl_str_mv Rosa,Flávia A. F. da
Rebelo,Ricardo A.
Nascimento,Maria G.
dc.subject.por.fl_str_mv indolecarboxylic acids
nitrene insertion
piperonal
plant growth regulator
topic indolecarboxylic acids
nitrene insertion
piperonal
plant growth regulator
description The synthesis of 5,6-methylenedioxy-indol-3-yl-methanoic acid 8 and 5,6-methylenedioxy-indol-3-yl-acetic acid 13 is described. Piperonal was employed as starting material, and the construction of the heterocyclic ring based on the Hemetsberger reaction of the corresponding beta-azidostyrene was highly regiospecific. Compound 8 was obtained as a key intermediate towards 13, and a Mannich reaction was used to introduce the required alkyl side chain. The route comprised eight steps giving 13 in 26% overall yield. The formation of the indolic ring via reductive cyclisation of o,beta-dinitrostyrene is also presented.
publishDate 2003
dc.date.none.fl_str_mv 2003-01-01
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=S0103-50532003000100003
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000100003
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532003000100003
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.14 n.1 2003
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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