2-methyl-7-substituted pyrazolo[1,5-a]pyrimidines: highly regioselective synthesis and bromination

Detalhes bibliográficos
Autor(a) principal: Martins,Marcos A. P.
Data de Publicação: 2009
Outros Autores: Scapin,Elisandra, Frizzo,Clarissa P., Rosa,Fernanda A., Bonacorso,Helio G., Zanatta,Nilo
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=S0103-50532009000200003
Resumo: The reaction of 3-amino-5-methyl-1H-pyrazole with 1,1,1-trichloro-4-alkoxy-3-alken-2-ones [CCl3C(O)CH=C(R¹)OR, where R¹/R = H/Me, Me/Et, Et/Me, Pr/Et, Bu/Me, iso-Bu/Me] or β-dimethylaminovinyl ketones [R²C(O)CH=CHNMe2, where R² = Ph, Ph-4-Me, Ph-4-F, Ph-4-Cl, Ph-4-Br, Ph-4-NO2, fur-2-yl, thien-2-yl, pyrrol-2-yl, pyrid-2-yl], in acetic acid under reflux for 16 hours, furnished highly regioselective the halomethylated pyrazolo[1,5-a]pyrimidines and aryl[heteroaryl]pyrazolo[1,5-a]pyrimidines, respectively. A protocol for the bromination reaction at the 3-position pyrazolo[1,5-a]pyrimidines also was investigated.
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spelling 2-methyl-7-substituted pyrazolo[1,5-a]pyrimidines: highly regioselective synthesis and brominationpyrimidinespyrazolespyrazolo[1,5-a]pyrimidinesenonesbrominationThe reaction of 3-amino-5-methyl-1H-pyrazole with 1,1,1-trichloro-4-alkoxy-3-alken-2-ones [CCl3C(O)CH=C(R¹)OR, where R¹/R = H/Me, Me/Et, Et/Me, Pr/Et, Bu/Me, iso-Bu/Me] or β-dimethylaminovinyl ketones [R²C(O)CH=CHNMe2, where R² = Ph, Ph-4-Me, Ph-4-F, Ph-4-Cl, Ph-4-Br, Ph-4-NO2, fur-2-yl, thien-2-yl, pyrrol-2-yl, pyrid-2-yl], in acetic acid under reflux for 16 hours, furnished highly regioselective the halomethylated pyrazolo[1,5-a]pyrimidines and aryl[heteroaryl]pyrazolo[1,5-a]pyrimidines, respectively. A protocol for the bromination reaction at the 3-position pyrazolo[1,5-a]pyrimidines also was investigated.Sociedade Brasileira de Química2009-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000200003Journal of the Brazilian Chemical Society v.20 n.2 2009reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532009000200003info:eu-repo/semantics/openAccessMartins,Marcos A. P.Scapin,ElisandraFrizzo,Clarissa P.Rosa,Fernanda A.Bonacorso,Helio G.Zanatta,Niloeng2009-03-02T00:00:00Zoai:scielo:S0103-50532009000200003Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2009-03-02T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv 2-methyl-7-substituted pyrazolo[1,5-a]pyrimidines: highly regioselective synthesis and bromination
title 2-methyl-7-substituted pyrazolo[1,5-a]pyrimidines: highly regioselective synthesis and bromination
spellingShingle 2-methyl-7-substituted pyrazolo[1,5-a]pyrimidines: highly regioselective synthesis and bromination
Martins,Marcos A. P.
pyrimidines
pyrazoles
pyrazolo[1,5-a]pyrimidines
enones
bromination
title_short 2-methyl-7-substituted pyrazolo[1,5-a]pyrimidines: highly regioselective synthesis and bromination
title_full 2-methyl-7-substituted pyrazolo[1,5-a]pyrimidines: highly regioselective synthesis and bromination
title_fullStr 2-methyl-7-substituted pyrazolo[1,5-a]pyrimidines: highly regioselective synthesis and bromination
title_full_unstemmed 2-methyl-7-substituted pyrazolo[1,5-a]pyrimidines: highly regioselective synthesis and bromination
title_sort 2-methyl-7-substituted pyrazolo[1,5-a]pyrimidines: highly regioselective synthesis and bromination
author Martins,Marcos A. P.
author_facet Martins,Marcos A. P.
Scapin,Elisandra
Frizzo,Clarissa P.
Rosa,Fernanda A.
Bonacorso,Helio G.
Zanatta,Nilo
author_role author
author2 Scapin,Elisandra
Frizzo,Clarissa P.
Rosa,Fernanda A.
Bonacorso,Helio G.
Zanatta,Nilo
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Martins,Marcos A. P.
Scapin,Elisandra
Frizzo,Clarissa P.
Rosa,Fernanda A.
Bonacorso,Helio G.
Zanatta,Nilo
dc.subject.por.fl_str_mv pyrimidines
pyrazoles
pyrazolo[1,5-a]pyrimidines
enones
bromination
topic pyrimidines
pyrazoles
pyrazolo[1,5-a]pyrimidines
enones
bromination
description The reaction of 3-amino-5-methyl-1H-pyrazole with 1,1,1-trichloro-4-alkoxy-3-alken-2-ones [CCl3C(O)CH=C(R¹)OR, where R¹/R = H/Me, Me/Et, Et/Me, Pr/Et, Bu/Me, iso-Bu/Me] or β-dimethylaminovinyl ketones [R²C(O)CH=CHNMe2, where R² = Ph, Ph-4-Me, Ph-4-F, Ph-4-Cl, Ph-4-Br, Ph-4-NO2, fur-2-yl, thien-2-yl, pyrrol-2-yl, pyrid-2-yl], in acetic acid under reflux for 16 hours, furnished highly regioselective the halomethylated pyrazolo[1,5-a]pyrimidines and aryl[heteroaryl]pyrazolo[1,5-a]pyrimidines, respectively. A protocol for the bromination reaction at the 3-position pyrazolo[1,5-a]pyrimidines also was investigated.
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=S0103-50532009000200003
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000200003
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532009000200003
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.20 n.2 2009
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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