A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-Laccase

Detalhes bibliográficos
Autor(a) principal: Sousa, Ana Catarina
Data de Publicação: 2018
Outros Autores: Oliveira, Maria Conceição, Martins, Lígia O., Robalo, Maria Paula
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10400.21/7998
Resumo: An efficient and sustainable one-step procedure for the synthesis of new asymmetric phenazines and phenoxazinones from commercially available ortho-substituted diamines and ortho-substituted hydroxyamines is reported. In this study we have expanded the substrate scope of CotA-laccase-catalyzed aerobic oxidations through the use of aromatic amines presenting variable functional groups, including N-substitution, contributing to the rational synthesis of different heterocyclic scaffolds. The transformations proceed smoothly through a cascade of oxidative reactions to the benzoquinonediimine intermediates followed by nucleophilic addition, intramolecular cyclization and aromatization, all performed in mild conditions.
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spelling A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-LaccaseBiocatalysisHomocoupling reactionsLaccaseNitrogen heterocyclesOxidationAn efficient and sustainable one-step procedure for the synthesis of new asymmetric phenazines and phenoxazinones from commercially available ortho-substituted diamines and ortho-substituted hydroxyamines is reported. In this study we have expanded the substrate scope of CotA-laccase-catalyzed aerobic oxidations through the use of aromatic amines presenting variable functional groups, including N-substitution, contributing to the rational synthesis of different heterocyclic scaffolds. The transformations proceed smoothly through a cascade of oxidative reactions to the benzoquinonediimine intermediates followed by nucleophilic addition, intramolecular cyclization and aromatization, all performed in mild conditions.WileyRCIPLSousa, Ana CatarinaOliveira, Maria ConceiçãoMartins, Lígia O.Robalo, Maria Paula2018-01-31T11:39:12Z2018-02-012018-02-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.21/7998engSOUSA, Ana Catarina; [et al] – A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-Laccase. Advanced Shyntesis & Catalysis. ISSN 1615-4169. Vol. 360, N.º 3 (2018), pp. 575-5831615-416910.1002/adsc.201701228metadata only accessinfo: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:RCAAP2023-08-03T09:54:50Zoai:repositorio.ipl.pt:10400.21/7998Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:16:50.609028Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-Laccase
title A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-Laccase
spellingShingle A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-Laccase
Sousa, Ana Catarina
Biocatalysis
Homocoupling reactions
Laccase
Nitrogen heterocycles
Oxidation
title_short A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-Laccase
title_full A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-Laccase
title_fullStr A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-Laccase
title_full_unstemmed A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-Laccase
title_sort A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-Laccase
author Sousa, Ana Catarina
author_facet Sousa, Ana Catarina
Oliveira, Maria Conceição
Martins, Lígia O.
Robalo, Maria Paula
author_role author
author2 Oliveira, Maria Conceição
Martins, Lígia O.
Robalo, Maria Paula
author2_role author
author
author
dc.contributor.none.fl_str_mv RCIPL
dc.contributor.author.fl_str_mv Sousa, Ana Catarina
Oliveira, Maria Conceição
Martins, Lígia O.
Robalo, Maria Paula
dc.subject.por.fl_str_mv Biocatalysis
Homocoupling reactions
Laccase
Nitrogen heterocycles
Oxidation
topic Biocatalysis
Homocoupling reactions
Laccase
Nitrogen heterocycles
Oxidation
description An efficient and sustainable one-step procedure for the synthesis of new asymmetric phenazines and phenoxazinones from commercially available ortho-substituted diamines and ortho-substituted hydroxyamines is reported. In this study we have expanded the substrate scope of CotA-laccase-catalyzed aerobic oxidations through the use of aromatic amines presenting variable functional groups, including N-substitution, contributing to the rational synthesis of different heterocyclic scaffolds. The transformations proceed smoothly through a cascade of oxidative reactions to the benzoquinonediimine intermediates followed by nucleophilic addition, intramolecular cyclization and aromatization, all performed in mild conditions.
publishDate 2018
dc.date.none.fl_str_mv 2018-01-31T11:39:12Z
2018-02-01
2018-02-01T00:00:00Z
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/10400.21/7998
url http://hdl.handle.net/10400.21/7998
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv SOUSA, Ana Catarina; [et al] – A sustainable synthesis of asymmetric phenazines and phenoxazinones mediated by CotA-Laccase. Advanced Shyntesis & Catalysis. ISSN 1615-4169. Vol. 360, N.º 3 (2018), pp. 575-583
1615-4169
10.1002/adsc.201701228
dc.rights.driver.fl_str_mv metadata only access
info:eu-repo/semantics/openAccess
rights_invalid_str_mv metadata only access
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
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
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
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reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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