Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry

This is the peer reviewed version of the following article: European Journal of Organic Chemistry 2015.32 (2015): 7160-7175, which has been published in final form at http://dx.doi.org/10486/10.1002/ejoc.201501026

Detalles Bibliográficos
Autores: Bilbao, Nerea, Vázquez-González, Violeta, Aranda, M. Teresa, González Rodríguez, David
Tipo de recurso: artículo
Fecha de publicación:2015
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/672456
Acceso en línea:http://hdl.handle.net/10486/672456
https://dx.doi.org/10.1002/ejoc.201501026
Access Level:acceso abierto
Palabra clave:Alkylation
Cross-coupling
Nitrogen heterocycles
Nucleobases
Self-assembly
Supramolecular chemistry
Química
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spelling Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular ChemistryBilbao, NereaVázquez-González, VioletaAranda, M. TeresaGonzález Rodríguez, DavidAlkylationCross-couplingNitrogen heterocyclesNucleobasesSelf-assemblySupramolecular chemistryQuímicaThis is the peer reviewed version of the following article: European Journal of Organic Chemistry 2015.32 (2015): 7160-7175, which has been published in final form at http://dx.doi.org/10486/10.1002/ejoc.201501026A series of lipophilic nucleobases that are substituted at the 5- (pyrimidines) or 8- (purines) position with either a halogen atom or a terminal triple bond have been synthesized. The sequences and reactions studied in this work, which mainly comprise halogenation, alkylation, Sonogashira coupling, and trimethylsilylacetylene deprotection, have been carefully optimized, to reach the final compounds in the most straightforward and convenient way, with the highest possible purity and yield. These compounds include cytosine, isocytosine, and uracil derivatives as pyrimidine heterocycles, and guanine, isoguanine, and 2-aminoadenine derivatives as complementary purine bases. Variability was introduced at the N-1/N-9 positions of these pyrimidine/purine nucleobases, which were functionalized with alkyl or benzyl groups, as well as with protected amine or carboxylic acid substituents. The molecules prepared constitute a useful collection of synthetic intermediates for the field of chemical self-assembly. A series of lipophilic nucleobases substituted at the 5- (pyrimidines) or 8-position (purines) with either a halogen atom or a terminal triple bond have been synthesized. These molecules comprise a useful collection of synthetic intermediates for the field of chemical self-assemblyFunding from the European Research Council (ERC-StG 279548) and MINECO (CTQ2011-23659) is gratefully acknowledged. V.V.-G. is grateful for a F.P.I. fellowship from MINECO.Wiley-VCH VerlagDepartamento de Química OrgánicaFacultad de Ciencias20152015-11-01research articlehttp://purl.org/coar/resource_type/c_2df8fbb1AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10486/672456https://dx.doi.org/10.1002/ejoc.201501026reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengEuropean Commission http://dx.doi.org/10.13039/501100000780 Framework Programme Seven 279548open accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/6724562026-06-23T12:46:27Z
dc.title.none.fl_str_mv Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry
title Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry
spellingShingle Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry
Bilbao, Nerea
Alkylation
Cross-coupling
Nitrogen heterocycles
Nucleobases
Self-assembly
Supramolecular chemistry
Química
title_short Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry
title_full Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry
title_fullStr Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry
title_full_unstemmed Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry
title_sort Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry
dc.creator.none.fl_str_mv Bilbao, Nerea
Vázquez-González, Violeta
Aranda, M. Teresa
González Rodríguez, David
author Bilbao, Nerea
author_facet Bilbao, Nerea
Vázquez-González, Violeta
Aranda, M. Teresa
González Rodríguez, David
author_role author
author2 Vázquez-González, Violeta
Aranda, M. Teresa
González Rodríguez, David
author2_role author
author
author
dc.contributor.none.fl_str_mv Departamento de Química Orgánica
Facultad de Ciencias
dc.subject.none.fl_str_mv Alkylation
Cross-coupling
Nitrogen heterocycles
Nucleobases
Self-assembly
Supramolecular chemistry
Química
topic Alkylation
Cross-coupling
Nitrogen heterocycles
Nucleobases
Self-assembly
Supramolecular chemistry
Química
description This is the peer reviewed version of the following article: European Journal of Organic Chemistry 2015.32 (2015): 7160-7175, which has been published in final form at http://dx.doi.org/10486/10.1002/ejoc.201501026
publishDate 2015
dc.date.none.fl_str_mv 2015
2015-11-01
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10486/672456
https://dx.doi.org/10.1002/ejoc.201501026
url http://hdl.handle.net/10486/672456
https://dx.doi.org/10.1002/ejoc.201501026
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv European Commission http://dx.doi.org/10.13039/501100000780 Framework Programme Seven 279548
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
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:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300724

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