Synthesis of Benzomacrolactam by 11endo Selective Aryl Radical Cyclization of 2Iodobenzamide Derived from DGalactose
Autor(a) principal: | |
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Data de Publicação: | 2002 |
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=S0103-50532002000500005 |
Resumo: | Encouraged by our previous studies of tri-n-butyltin-mediated radical cyclization reaction of o-iodobenzamides, we applied this methodology to the synthesis of benzomacrolactam 2 from methyl 4-O-allyl-2,3-di-O-benzyl-6-deoxy-6-(2-iodobenzoylamino)- α-D-galactopyranoside 1. Apart from the macrolactam 2, resulting from regioselective 11-endo aryl radical cyclization, the hydrogenolysis produt 3 was obtained. The o-iodobenzamide 1 was prepared in eight conventional synthetic steps from methyl α-D-galactopyranoside. The unequivocal structures of 1, 2 and 3 were supported by ¹H, 13C and DEPT NMR spectroscopy and by COSY and HMQC experiments. |
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Journal of the Brazilian Chemical Society (Online) |
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Synthesis of Benzomacrolactam by 11endo Selective Aryl Radical Cyclization of 2Iodobenzamide Derived from DGalactosebenzomacrolactamaryl radical cyclizationEncouraged by our previous studies of tri-n-butyltin-mediated radical cyclization reaction of o-iodobenzamides, we applied this methodology to the synthesis of benzomacrolactam 2 from methyl 4-O-allyl-2,3-di-O-benzyl-6-deoxy-6-(2-iodobenzoylamino)- α-D-galactopyranoside 1. Apart from the macrolactam 2, resulting from regioselective 11-endo aryl radical cyclization, the hydrogenolysis produt 3 was obtained. The o-iodobenzamide 1 was prepared in eight conventional synthetic steps from methyl α-D-galactopyranoside. The unequivocal structures of 1, 2 and 3 were supported by ¹H, 13C and DEPT NMR spectroscopy and by COSY and HMQC experiments.Sociedade Brasileira de Química2002-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000500005Journal of the Brazilian Chemical Society v.13 n.5 2002reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532002000500005info:eu-repo/semantics/openAccessBinatti,IldefonsoPrado,Maria Auxiliadôra F.Alves,Ricardo J.Souza Filho,José D.eng2008-10-08T00:00:00Zoai:scielo:S0103-50532002000500005Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2008-10-08T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Synthesis of Benzomacrolactam by 11endo Selective Aryl Radical Cyclization of 2Iodobenzamide Derived from DGalactose |
title |
Synthesis of Benzomacrolactam by 11endo Selective Aryl Radical Cyclization of 2Iodobenzamide Derived from DGalactose |
spellingShingle |
Synthesis of Benzomacrolactam by 11endo Selective Aryl Radical Cyclization of 2Iodobenzamide Derived from DGalactose Binatti,Ildefonso benzomacrolactam aryl radical cyclization |
title_short |
Synthesis of Benzomacrolactam by 11endo Selective Aryl Radical Cyclization of 2Iodobenzamide Derived from DGalactose |
title_full |
Synthesis of Benzomacrolactam by 11endo Selective Aryl Radical Cyclization of 2Iodobenzamide Derived from DGalactose |
title_fullStr |
Synthesis of Benzomacrolactam by 11endo Selective Aryl Radical Cyclization of 2Iodobenzamide Derived from DGalactose |
title_full_unstemmed |
Synthesis of Benzomacrolactam by 11endo Selective Aryl Radical Cyclization of 2Iodobenzamide Derived from DGalactose |
title_sort |
Synthesis of Benzomacrolactam by 11endo Selective Aryl Radical Cyclization of 2Iodobenzamide Derived from DGalactose |
author |
Binatti,Ildefonso |
author_facet |
Binatti,Ildefonso Prado,Maria Auxiliadôra F. Alves,Ricardo J. Souza Filho,José D. |
author_role |
author |
author2 |
Prado,Maria Auxiliadôra F. Alves,Ricardo J. Souza Filho,José D. |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Binatti,Ildefonso Prado,Maria Auxiliadôra F. Alves,Ricardo J. Souza Filho,José D. |
dc.subject.por.fl_str_mv |
benzomacrolactam aryl radical cyclization |
topic |
benzomacrolactam aryl radical cyclization |
description |
Encouraged by our previous studies of tri-n-butyltin-mediated radical cyclization reaction of o-iodobenzamides, we applied this methodology to the synthesis of benzomacrolactam 2 from methyl 4-O-allyl-2,3-di-O-benzyl-6-deoxy-6-(2-iodobenzoylamino)- α-D-galactopyranoside 1. Apart from the macrolactam 2, resulting from regioselective 11-endo aryl radical cyclization, the hydrogenolysis produt 3 was obtained. The o-iodobenzamide 1 was prepared in eight conventional synthetic steps from methyl α-D-galactopyranoside. The unequivocal structures of 1, 2 and 3 were supported by ¹H, 13C and DEPT NMR spectroscopy and by COSY and HMQC experiments. |
publishDate |
2002 |
dc.date.none.fl_str_mv |
2002-09-01 |
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=S0103-50532002000500005 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000500005 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532002000500005 |
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.13 n.5 2002 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_ |
1750318164938326016 |