Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine core

Detalhes bibliográficos
Autor(a) principal: Sá, Marcus Mandolesi
Data de Publicação: 2010
Outros Autores: Ferreira, Misael, Bortoluzzi, Adailton João, Fernandes, Luciano Gonçalves, Cunha, Silvio do Desterro
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFBA
Texto Completo: http://www.repositorio.ufba.br/ri/handle/ri/12096
Resumo: p.303-321
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spelling Sá, Marcus MandolesiFerreira, MisaelBortoluzzi, Adailton JoãoFernandes, Luciano GonçalvesCunha, Silvio do DesterroSá, Marcus MandolesiFerreira, MisaelBortoluzzi, Adailton JoãoFernandes, Luciano GonçalvesCunha, Silvio do Desterro2013-07-04T13:04:53Z2013-07-04T13:04:53Z20101551-7004http://www.repositorio.ufba.br/ri/handle/ri/12096v. 2010, n. 11p.303-321The reactivity profile of allylic bromides (derived from the Morita-Baylis-Hillman reaction) towards thiourea derivatives and further transformations of the resulting isothiuronium bromides are described. Isothiuronium salts, prepared in near quantitative yields, undergo a selective acetylation or a base-promoted intramolecular cyclization to give 2-amino-1,3-thiazin-4-ones in good overall yields. Besides the simplicity of the reaction, conditions, and purification steps, the methods presented here furnished high-purity products. The structural characterization of representative compounds was unequivocally confirmed by X-ray diffraction analysis.Submitted by Suelen Reis (suziy.ellen@gmail.com) on 2013-07-04T13:04:53Z No. of bitstreams: 1 Marcus M. Sá.pdf: 477609 bytes, checksum: 7a03da5e6a1af957bcff9c8ea60a5303 (MD5)Made available in DSpace on 2013-07-04T13:04:53Z (GMT). No. of bitstreams: 1 Marcus M. Sá.pdf: 477609 bytes, checksum: 7a03da5e6a1af957bcff9c8ea60a5303 (MD5) Previous issue date: 2010http://dx.doi.org/10.3998/ark.5550190.0011.b24reponame:Repositório Institucional da UFBAinstname:Universidade Federal da Bahia (UFBA)instacron:UFBA1,3-thiazinoneAllylic bromideAqueous solventIsothiuronium saltExploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine coreARKIVOC - Online Journal of Organic Chemistryinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleenginfo:eu-repo/semantics/openAccessORIGINALMarcus M. Sá.pdfMarcus M. Sá.pdfapplication/pdf477609https://repositorio.ufba.br/bitstream/ri/12096/1/Marcus%20M.%20S%c3%a1.pdf7a03da5e6a1af957bcff9c8ea60a5303MD51LICENSElicense.txtlicense.txttext/plain1762https://repositorio.ufba.br/bitstream/ri/12096/2/license.txt1b89a9a0548218172d7c829f87a0eab9MD52TEXTMarcus M. Sá.pdf.txtMarcus M. 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dc.title.pt_BR.fl_str_mv Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine core
dc.title.alternative.pt_BR.fl_str_mv ARKIVOC - Online Journal of Organic Chemistry
title Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine core
spellingShingle Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine core
Sá, Marcus Mandolesi
1,3-thiazinone
Allylic bromide
Aqueous solvent
Isothiuronium salt
title_short Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine core
title_full Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine core
title_fullStr Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine core
title_full_unstemmed Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine core
title_sort Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine core
author Sá, Marcus Mandolesi
author_facet Sá, Marcus Mandolesi
Ferreira, Misael
Bortoluzzi, Adailton João
Fernandes, Luciano Gonçalves
Cunha, Silvio do Desterro
author_role author
author2 Ferreira, Misael
Bortoluzzi, Adailton João
Fernandes, Luciano Gonçalves
Cunha, Silvio do Desterro
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Sá, Marcus Mandolesi
Ferreira, Misael
Bortoluzzi, Adailton João
Fernandes, Luciano Gonçalves
Cunha, Silvio do Desterro
Sá, Marcus Mandolesi
Ferreira, Misael
Bortoluzzi, Adailton João
Fernandes, Luciano Gonçalves
Cunha, Silvio do Desterro
dc.subject.por.fl_str_mv 1,3-thiazinone
Allylic bromide
Aqueous solvent
Isothiuronium salt
topic 1,3-thiazinone
Allylic bromide
Aqueous solvent
Isothiuronium salt
description p.303-321
publishDate 2010
dc.date.issued.fl_str_mv 2010
dc.date.accessioned.fl_str_mv 2013-07-04T13:04:53Z
dc.date.available.fl_str_mv 2013-07-04T13:04:53Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://www.repositorio.ufba.br/ri/handle/ri/12096
dc.identifier.issn.none.fl_str_mv 1551-7004
dc.identifier.number.pt_BR.fl_str_mv v. 2010, n. 11
identifier_str_mv 1551-7004
v. 2010, n. 11
url http://www.repositorio.ufba.br/ri/handle/ri/12096
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.source.pt_BR.fl_str_mv http://dx.doi.org/10.3998/ark.5550190.0011.b24
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFBA
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reponame_str Repositório Institucional da UFBA
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