Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry

ABSTRACT: The synthesis of phenylnaphthalic anhydrides, including substitution patterns typically found in the Haemodoraceae and Pontederiacea family of plants, was explored using Suzuki and Ullmann-type aromatic substitutions on acenaphthene. Synthetic challenges were surmounted by tactical changes...

Full description

Autores:
Prieto Mesa, Ana María
Otálvaro Tamayo, Felipe
Paetz, Christian
Schneider, Bernd
Tipo de recurso:
Article of investigation
Fecha de publicación:
2024
Institución:
Universidad de Antioquia
Repositorio:
Repositorio UdeA
Idioma:
eng
OAI Identifier:
oai:bibliotecadigital.udea.edu.co:10495/37988
Acceso en línea:
https://hdl.handle.net/10495/37988
Palabra clave:
Phenylnaphthalic anhydrides
Acenaphthene chemistry
Suzuki coupling
Ullman-type substitution
Rights
openAccess
License
http://creativecommons.org/licenses/by-nc-nd/2.5/co/
id UDEA2_5af9f8680ac60d92b12cf3d11c438e58
oai_identifier_str oai:bibliotecadigital.udea.edu.co:10495/37988
network_acronym_str UDEA2
network_name_str Repositorio UdeA
repository_id_str
dc.title.spa.fl_str_mv Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry
title Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry
spellingShingle Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry
Phenylnaphthalic anhydrides
Acenaphthene chemistry
Suzuki coupling
Ullman-type substitution
title_short Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry
title_full Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry
title_fullStr Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry
title_full_unstemmed Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry
title_sort Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry
dc.creator.fl_str_mv Prieto Mesa, Ana María
Otálvaro Tamayo, Felipe
Paetz, Christian
Schneider, Bernd
dc.contributor.author.none.fl_str_mv Prieto Mesa, Ana María
Otálvaro Tamayo, Felipe
Paetz, Christian
Schneider, Bernd
dc.contributor.researchgroup.spa.fl_str_mv Síntesis y Biosíntesis de Metabolitos Naturales
dc.subject.proposal.spa.fl_str_mv Phenylnaphthalic anhydrides
Acenaphthene chemistry
Suzuki coupling
Ullman-type substitution
topic Phenylnaphthalic anhydrides
Acenaphthene chemistry
Suzuki coupling
Ullman-type substitution
description ABSTRACT: The synthesis of phenylnaphthalic anhydrides, including substitution patterns typically found in the Haemodoraceae and Pontederiacea family of plants, was explored using Suzuki and Ullmann-type aromatic substitutions on acenaphthene. Synthetic challenges were surmounted by tactical changes to determine the order of events.
publishDate 2024
dc.date.accessioned.none.fl_str_mv 2024-02-02T19:58:03Z
dc.date.available.none.fl_str_mv 2024-02-02T19:58:03Z
dc.date.issued.none.fl_str_mv 2024
dc.type.spa.fl_str_mv Artículo de investigación
dc.type.coar.spa.fl_str_mv http://purl.org/coar/resource_type/c_2df8fbb1
dc.type.redcol.spa.fl_str_mv https://purl.org/redcol/resource_type/ART
dc.type.coarversion.spa.fl_str_mv http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.driver.spa.fl_str_mv info:eu-repo/semantics/article
dc.type.version.spa.fl_str_mv info:eu-repo/semantics/publishedVersion
format http://purl.org/coar/resource_type/c_2df8fbb1
status_str publishedVersion
dc.identifier.citation.spa.fl_str_mv Prieto A, Paetz C, Schneider B, Otálvaro F. Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry. Tetrahedron Lett [Internet]. 2024;135:154907. Disponible en: https://www.sciencedirect.com/science/article/pii/S0040403924000017
dc.identifier.issn.none.fl_str_mv 0040-4039
dc.identifier.uri.none.fl_str_mv https://hdl.handle.net/10495/37988
dc.identifier.doi.none.fl_str_mv 10.1016/j.tetlet.2024.154907
identifier_str_mv Prieto A, Paetz C, Schneider B, Otálvaro F. Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry. Tetrahedron Lett [Internet]. 2024;135:154907. Disponible en: https://www.sciencedirect.com/science/article/pii/S0040403924000017
0040-4039
10.1016/j.tetlet.2024.154907
url https://hdl.handle.net/10495/37988
dc.language.iso.spa.fl_str_mv eng
language eng
dc.relation.ispartofjournalabbrev.spa.fl_str_mv Tetrahedron. Lett.
dc.relation.citationendpage.spa.fl_str_mv 4
dc.relation.citationstartpage.spa.fl_str_mv 1
dc.relation.citationvolume.spa.fl_str_mv 135
dc.relation.ispartofjournal.spa.fl_str_mv Tetrahedron Letters
dc.rights.uri.*.fl_str_mv http://creativecommons.org/licenses/by-nc-nd/2.5/co/
dc.rights.uri.spa.fl_str_mv https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rights.accessrights.spa.fl_str_mv info:eu-repo/semantics/openAccess
dc.rights.coar.spa.fl_str_mv http://purl.org/coar/access_right/c_abf2
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-nd/2.5/co/
https://creativecommons.org/licenses/by-nc-nd/4.0/
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.extent.spa.fl_str_mv 4
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.publisher.spa.fl_str_mv Elsevier
dc.publisher.place.spa.fl_str_mv Oxford, Inglaterra
institution Universidad de Antioquia
bitstream.url.fl_str_mv https://bibliotecadigital.udea.edu.co/bitstreams/862f9e1f-0c26-4039-b31a-866377f17032/download
https://bibliotecadigital.udea.edu.co/bitstreams/aef5c79b-4c9e-4196-b1dc-63e2a9784373/download
https://bibliotecadigital.udea.edu.co/bitstreams/67203e2c-1fe6-4d19-adc3-43dfd0dbccf4/download
https://bibliotecadigital.udea.edu.co/bitstreams/c59f7255-3786-4632-8f25-933aa40bfd3d/download
https://bibliotecadigital.udea.edu.co/bitstreams/cdd300b4-a498-4ebd-b69e-5b68d949e712/download
bitstream.checksum.fl_str_mv 8a4605be74aa9ea9d79846c1fba20a33
b88b088d9957e670ce3b3fbe2eedbc13
43dd850f7a066109651ff03661b86ff3
e70e138e323d7ec458bb382b6e51df6c
a85a49697ff6315182a63d0bab849459
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
MD5
MD5
repository.name.fl_str_mv Repositorio Institucional de la Universidad de Antioquia
repository.mail.fl_str_mv aplicacionbibliotecadigitalbiblioteca@udea.edu.co
_version_ 1851052283561771008
spelling Prieto Mesa, Ana MaríaOtálvaro Tamayo, FelipePaetz, ChristianSchneider, BerndSíntesis y Biosíntesis de Metabolitos Naturales2024-02-02T19:58:03Z2024-02-02T19:58:03Z2024Prieto A, Paetz C, Schneider B, Otálvaro F. Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistry. Tetrahedron Lett [Internet]. 2024;135:154907. Disponible en: https://www.sciencedirect.com/science/article/pii/S00404039240000170040-4039https://hdl.handle.net/10495/3798810.1016/j.tetlet.2024.154907ABSTRACT: The synthesis of phenylnaphthalic anhydrides, including substitution patterns typically found in the Haemodoraceae and Pontederiacea family of plants, was explored using Suzuki and Ullmann-type aromatic substitutions on acenaphthene. Synthetic challenges were surmounted by tactical changes to determine the order of events.Universidad de Antioquia. Vicerrectoría de investigación. Comité para el Desarrollo de la Investigación - CODIMax Planck Institute for Chemical EcologyCOL00696894application/pdfengElsevierOxford, Inglaterrahttp://creativecommons.org/licenses/by-nc-nd/2.5/co/https://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Synthesis of 5-phenyl-1,8-naphthalic anhydrides: An exercise in acenaphthene chemistryArtículo de investigaciónhttp://purl.org/coar/resource_type/c_2df8fbb1https://purl.org/redcol/resource_type/ARThttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionPhenylnaphthalic anhydridesAcenaphthene chemistrySuzuki couplingUllman-type substitutionTetrahedron. Lett.41135Tetrahedron LettersES84220018RoR:03bp5hc83RoR:02ks53214PublicationLICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://bibliotecadigital.udea.edu.co/bitstreams/862f9e1f-0c26-4039-b31a-866377f17032/download8a4605be74aa9ea9d79846c1fba20a33MD53falseAnonymousREADCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8823https://bibliotecadigital.udea.edu.co/bitstreams/aef5c79b-4c9e-4196-b1dc-63e2a9784373/downloadb88b088d9957e670ce3b3fbe2eedbc13MD52falseAnonymousREADORIGINALPrietoAna_2024_Synthesis5Phenyl1.pdfPrietoAna_2024_Synthesis5Phenyl1.pdfArtículo de investigaciónapplication/pdf591576https://bibliotecadigital.udea.edu.co/bitstreams/67203e2c-1fe6-4d19-adc3-43dfd0dbccf4/download43dd850f7a066109651ff03661b86ff3MD51trueAnonymousREADTEXTPrietoAna_2024_Synthesis5Phenyl1.pdf.txtPrietoAna_2024_Synthesis5Phenyl1.pdf.txtExtracted texttext/plain23148https://bibliotecadigital.udea.edu.co/bitstreams/c59f7255-3786-4632-8f25-933aa40bfd3d/downloade70e138e323d7ec458bb382b6e51df6cMD54falseAnonymousREADTHUMBNAILPrietoAna_2024_Synthesis5Phenyl1.pdf.jpgPrietoAna_2024_Synthesis5Phenyl1.pdf.jpgGenerated Thumbnailimage/jpeg15290https://bibliotecadigital.udea.edu.co/bitstreams/cdd300b4-a498-4ebd-b69e-5b68d949e712/downloada85a49697ff6315182a63d0bab849459MD55falseAnonymousREAD10495/37988oai:bibliotecadigital.udea.edu.co:10495/379882025-03-26 19:52:41.394http://creativecommons.org/licenses/by-nc-nd/2.5/co/open.accesshttps://bibliotecadigital.udea.edu.coRepositorio Institucional de la Universidad de Antioquiaaplicacionbibliotecadigitalbiblioteca@udea.edu.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