Regioselective alkylation reaction of purines under microwave irradiation

The alkylation of purines which is generally carried out after anion formation by treatment with a base and alkyl halide is complicated and in the best cases, mixtures of N-alkylated compounds are obtained. Purine derivatives can be acquired from alkylation at N-7 and N-9. In this work, the reaction...

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Autores: Vinuesa, Arturo, Viñas, Miquel, Jahani, Daniel, Ginard, Jaume, Mur, Nuria, Pujol Dilmé, M. Dolors
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2021
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/183716
Acceso en línea:https://hdl.handle.net/2445/183716
Access Level:acceso abierto
Palabra clave:Purines
Compostos heterocíclics
Síntesi orgànica
Heterocyclic compounds
Organic synthesis
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spelling Regioselective alkylation reaction of purines under microwave irradiationVinuesa, ArturoViñas, MiquelJahani, DanielGinard, JaumeMur, NuriaPujol Dilmé, M. DolorsPurinesCompostos heterocíclicsSíntesi orgànicaPurinesHeterocyclic compoundsOrganic synthesisThe alkylation of purines which is generally carried out after anion formation by treatment with a base and alkyl halide is complicated and in the best cases, mixtures of N-alkylated compounds are obtained. Purine derivatives can be acquired from alkylation at N-7 and N-9. In this work, the reaction conditions have been optimized to obtain the alkylation products of N-9 regioselectively. Different bases have been tried and tetrabutylammonium hydroxide has led to the best results. The reaction depends on the type of base and solvent used and improves considerably when the aid of microwave irradiation is used, which also considerably reduces the reaction time by reducing the formation of secondary products.Wiley2021info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://hdl.handle.net/2445/183716Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésReproducció del document publicat a: https://doi.org/10.1002/jhet.4407Journal of Heterocyclic Chemistry, 2021, vol. open access, p. open accesshttps://doi.org/10.1002/jhet.4407cc-by-nc-nd (c) Vinuesa, Arturo, et al.http://creativecommons.org/licenses/by-nc-nd/3.0/es/info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1837162026-05-27T06:46:51Z
dc.title.none.fl_str_mv Regioselective alkylation reaction of purines under microwave irradiation
title Regioselective alkylation reaction of purines under microwave irradiation
spellingShingle Regioselective alkylation reaction of purines under microwave irradiation
Vinuesa, Arturo
Purines
Compostos heterocíclics
Síntesi orgànica
Purines
Heterocyclic compounds
Organic synthesis
title_short Regioselective alkylation reaction of purines under microwave irradiation
title_full Regioselective alkylation reaction of purines under microwave irradiation
title_fullStr Regioselective alkylation reaction of purines under microwave irradiation
title_full_unstemmed Regioselective alkylation reaction of purines under microwave irradiation
title_sort Regioselective alkylation reaction of purines under microwave irradiation
dc.creator.none.fl_str_mv Vinuesa, Arturo
Viñas, Miquel
Jahani, Daniel
Ginard, Jaume
Mur, Nuria
Pujol Dilmé, M. Dolors
author Vinuesa, Arturo
author_facet Vinuesa, Arturo
Viñas, Miquel
Jahani, Daniel
Ginard, Jaume
Mur, Nuria
Pujol Dilmé, M. Dolors
author_role author
author2 Viñas, Miquel
Jahani, Daniel
Ginard, Jaume
Mur, Nuria
Pujol Dilmé, M. Dolors
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Purines
Compostos heterocíclics
Síntesi orgànica
Purines
Heterocyclic compounds
Organic synthesis
topic Purines
Compostos heterocíclics
Síntesi orgànica
Purines
Heterocyclic compounds
Organic synthesis
description The alkylation of purines which is generally carried out after anion formation by treatment with a base and alkyl halide is complicated and in the best cases, mixtures of N-alkylated compounds are obtained. Purine derivatives can be acquired from alkylation at N-7 and N-9. In this work, the reaction conditions have been optimized to obtain the alkylation products of N-9 regioselectively. Different bases have been tried and tetrabutylammonium hydroxide has led to the best results. The reaction depends on the type of base and solvent used and improves considerably when the aid of microwave irradiation is used, which also considerably reduces the reaction time by reducing the formation of secondary products.
publishDate 2021
dc.date.none.fl_str_mv 2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/183716
url https://hdl.handle.net/2445/183716
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: https://doi.org/10.1002/jhet.4407
Journal of Heterocyclic Chemistry, 2021, vol. open access, p. open access
https://doi.org/10.1002/jhet.4407
dc.rights.none.fl_str_mv cc-by-nc-nd (c) Vinuesa, Arturo, et al.
http://creativecommons.org/licenses/by-nc-nd/3.0/es/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by-nc-nd (c) Vinuesa, Arturo, et al.
http://creativecommons.org/licenses/by-nc-nd/3.0/es/
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 Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.301603

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