Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones

Detalhes bibliográficos
Autor(a) principal: Reddy,K. R. Kishore K.
Data de Publicação: 2013
Outros Autores: Silva Jr,Luiz F.
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=S0103-50532013000900004
Resumo: Iodine-catalyzed Prins cyclization of homoallylic alcohols and ketones was investigated. Anhydrous conditions and inert atmosphere are not required in this metal-free protocol. The reaction of 2-(3,4-dihydronaphthalen-1-yl)propan-1-ol with six aliphatic symmetric ketones gave the desired products in 67-77% yield. Cyclization was performed with four aliphatic unsymmetric ketones, leading to corresponding pyrans in 66-76% yield. Prins cyclization was also accomplished with four aromatic ketones in 37-66% yield. Finally, Prins cyclization of the monoterpene isopulegol and acetone was successfully achieved.
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spelling Iodine - catalyzed prins cyclization of aliphatic and aromatic ketonesiodinePrins cyclizationketonespyransspiro compoundsIodine-catalyzed Prins cyclization of homoallylic alcohols and ketones was investigated. Anhydrous conditions and inert atmosphere are not required in this metal-free protocol. The reaction of 2-(3,4-dihydronaphthalen-1-yl)propan-1-ol with six aliphatic symmetric ketones gave the desired products in 67-77% yield. Cyclization was performed with four aliphatic unsymmetric ketones, leading to corresponding pyrans in 66-76% yield. Prins cyclization was also accomplished with four aromatic ketones in 37-66% yield. Finally, Prins cyclization of the monoterpene isopulegol and acetone was successfully achieved.Sociedade Brasileira de Química2013-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000900004Journal of the Brazilian Chemical Society v.24 n.9 2013reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20130178info:eu-repo/semantics/openAccessReddy,K. R. Kishore K.Silva Jr,Luiz F.eng2013-09-24T00:00:00Zoai:scielo:S0103-50532013000900004Revistahttp://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 Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones
title Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones
spellingShingle Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones
Reddy,K. R. Kishore K.
iodine
Prins cyclization
ketones
pyrans
spiro compounds
title_short Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones
title_full Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones
title_fullStr Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones
title_full_unstemmed Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones
title_sort Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones
author Reddy,K. R. Kishore K.
author_facet Reddy,K. R. Kishore K.
Silva Jr,Luiz F.
author_role author
author2 Silva Jr,Luiz F.
author2_role author
dc.contributor.author.fl_str_mv Reddy,K. R. Kishore K.
Silva Jr,Luiz F.
dc.subject.por.fl_str_mv iodine
Prins cyclization
ketones
pyrans
spiro compounds
topic iodine
Prins cyclization
ketones
pyrans
spiro compounds
description Iodine-catalyzed Prins cyclization of homoallylic alcohols and ketones was investigated. Anhydrous conditions and inert atmosphere are not required in this metal-free protocol. The reaction of 2-(3,4-dihydronaphthalen-1-yl)propan-1-ol with six aliphatic symmetric ketones gave the desired products in 67-77% yield. Cyclization was performed with four aliphatic unsymmetric ketones, leading to corresponding pyrans in 66-76% yield. Prins cyclization was also accomplished with four aromatic ketones in 37-66% yield. Finally, Prins cyclization of the monoterpene isopulegol and acetone was successfully achieved.
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=S0103-50532013000900004
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000900004
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20130178
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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