Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones
Autor(a) principal: | |
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Data de Publicação: | 2013 |
Outros Autores: | |
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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Journal of the Brazilian Chemical Society (Online) |
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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 |
_version_ |
1750318175260508160 |