Synthesis and reactivity of beta-bromo-beta-substituted dehydroalanines

Detalhes bibliográficos
Autor(a) principal: Ferreira, Paula M. T.
Data de Publicação: 2006
Outros Autores: Monteiro, Luís S.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/72916
Resumo: The methyl ester of N-tert-butoxycarbonyl-(Z)-beta-bromo-beta-(1,2,4-triazol-1-yl)dehydroalanine was prepared by treatment of the methyl ester of N-tert-butoxycarbonyl-(E)-beta-(1,2,4-triazol-1-yl)dehydroalanine with N-bromosuccinimide (NBS), followed by Et3N. The reactivities of this compound and of our previously synthesized methyl ester of N-tert-butoxycarbonyl-beta,beta-dibromodehydroalanine towards several nucleophiles were studied, and it was found that these compounds react with oxygen nucleophiles to give the corresponding alpha-alkoxy-beta,beta-disubstituted alanines. Addition to the a-carbon atom also occurred when the beta,beta-dibromodehydroalanine derivative was treated with primary amines, giving alpha-amino-beta,beta-dibromoalanines. Treatment of the beta-bromo-beta-(1,2,4-triazol-1-yl)dehydroalanine derivative with amines gave alpha-(alkylamino)-beta-(alkylimino)alanines in high yields. These iminoalanines afforded alpha-aminoglycines when treated with silica in dichloromethane. (c) Wiley-VCH Verlag GmbH & Co.
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spelling Synthesis and reactivity of beta-bromo-beta-substituted dehydroalaninesNonproteinogenic amino acidsAlanine derivativesGlycine derivativesScience & TechnologyThe methyl ester of N-tert-butoxycarbonyl-(Z)-beta-bromo-beta-(1,2,4-triazol-1-yl)dehydroalanine was prepared by treatment of the methyl ester of N-tert-butoxycarbonyl-(E)-beta-(1,2,4-triazol-1-yl)dehydroalanine with N-bromosuccinimide (NBS), followed by Et3N. The reactivities of this compound and of our previously synthesized methyl ester of N-tert-butoxycarbonyl-beta,beta-dibromodehydroalanine towards several nucleophiles were studied, and it was found that these compounds react with oxygen nucleophiles to give the corresponding alpha-alkoxy-beta,beta-disubstituted alanines. Addition to the a-carbon atom also occurred when the beta,beta-dibromodehydroalanine derivative was treated with primary amines, giving alpha-amino-beta,beta-dibromoalanines. Treatment of the beta-bromo-beta-(1,2,4-triazol-1-yl)dehydroalanine derivative with amines gave alpha-(alkylamino)-beta-(alkylimino)alanines in high yields. These iminoalanines afforded alpha-aminoglycines when treated with silica in dichloromethane. (c) Wiley-VCH Verlag GmbH & Co.Thanks are due to the Fundação para a Ciência e Tecnologia (Por tugal) and FEDER for funding Centro de Química-Universidade do Minho and for financial support through project POCI/QUI/ 59407/2004.Wiley-VCH VerlagUniversidade do MinhoFerreira, Paula M. T.Monteiro, Luís S.2006-072006-07-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/72916eng1434-193X10.1002/ejoc.200600094https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.200600094info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T11:59:38ZPortal AgregadorONG
dc.title.none.fl_str_mv Synthesis and reactivity of beta-bromo-beta-substituted dehydroalanines
title Synthesis and reactivity of beta-bromo-beta-substituted dehydroalanines
spellingShingle Synthesis and reactivity of beta-bromo-beta-substituted dehydroalanines
Ferreira, Paula M. T.
Nonproteinogenic amino acids
Alanine derivatives
Glycine derivatives
Science & Technology
title_short Synthesis and reactivity of beta-bromo-beta-substituted dehydroalanines
title_full Synthesis and reactivity of beta-bromo-beta-substituted dehydroalanines
title_fullStr Synthesis and reactivity of beta-bromo-beta-substituted dehydroalanines
title_full_unstemmed Synthesis and reactivity of beta-bromo-beta-substituted dehydroalanines
title_sort Synthesis and reactivity of beta-bromo-beta-substituted dehydroalanines
author Ferreira, Paula M. T.
author_facet Ferreira, Paula M. T.
Monteiro, Luís S.
author_role author
author2 Monteiro, Luís S.
author2_role author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Ferreira, Paula M. T.
Monteiro, Luís S.
dc.subject.por.fl_str_mv Nonproteinogenic amino acids
Alanine derivatives
Glycine derivatives
Science & Technology
topic Nonproteinogenic amino acids
Alanine derivatives
Glycine derivatives
Science & Technology
description The methyl ester of N-tert-butoxycarbonyl-(Z)-beta-bromo-beta-(1,2,4-triazol-1-yl)dehydroalanine was prepared by treatment of the methyl ester of N-tert-butoxycarbonyl-(E)-beta-(1,2,4-triazol-1-yl)dehydroalanine with N-bromosuccinimide (NBS), followed by Et3N. The reactivities of this compound and of our previously synthesized methyl ester of N-tert-butoxycarbonyl-beta,beta-dibromodehydroalanine towards several nucleophiles were studied, and it was found that these compounds react with oxygen nucleophiles to give the corresponding alpha-alkoxy-beta,beta-disubstituted alanines. Addition to the a-carbon atom also occurred when the beta,beta-dibromodehydroalanine derivative was treated with primary amines, giving alpha-amino-beta,beta-dibromoalanines. Treatment of the beta-bromo-beta-(1,2,4-triazol-1-yl)dehydroalanine derivative with amines gave alpha-(alkylamino)-beta-(alkylimino)alanines in high yields. These iminoalanines afforded alpha-aminoglycines when treated with silica in dichloromethane. (c) Wiley-VCH Verlag GmbH & Co.
publishDate 2006
dc.date.none.fl_str_mv 2006-07
2006-07-01T00:00:00Z
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://hdl.handle.net/1822/72916
url http://hdl.handle.net/1822/72916
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1434-193X
10.1002/ejoc.200600094
https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.200600094
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH Verlag
publisher.none.fl_str_mv Wiley-VCH Verlag
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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instacron_str RCAAP
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