Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes

Autores
de la Torre, José M.; Nogueras, Manuel; Borkowski, Eduardo Jorge; Suvire, Fernando D.; Enriz, Ricardo Daniel; Cobo, Justo
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Pyrimidine-5-carbaldehyde derivatives, of easy access, were selected as precursors for the synthesis of mimic pteridine derivatives 5,6-dihydropyrimido[4,5-d]pyrimidines and 5,6,7,8- tetrahydropyrimido[4,5-d]pyrimidines via 4-amino-(5-aminomethyl)pyrimidine intermediates. Straightforward procedures allow a quick access to these compounds. The dihydro derivatives were prepared means of a final cyclocondensation carried out with orthoesters, catalysed by acid and assisted by microwaves irradiation under solvent free conditions. The final cyclocondensation with carbonyl compounds forming the tetrahydro derivatives was done under mild conditions, in which stereochemical induction was carried out on the building of this skeleton, and stereochemistry assignments corroborated by theoretical calculations.
Fil: de la Torre, José M.. Universidad de Jaén; España
Fil: Nogueras, Manuel. Universidad de Jaén; España
Fil: Borkowski, Eduardo Jorge. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Suvire, Fernando D.. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Cobo, Justo. Universidad de Jaén; España
Materia
4-Amino-5-(aminomethyl)pyrimidines
Microwave irradiation; ; ; cyclocondensation;
Theoretical calculations
Acid catalysis
Cyclocondensation
Stereoselectivity
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/14627
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/14627
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydesde la Torre, José M.Nogueras, ManuelBorkowski, Eduardo JorgeSuvire, Fernando D.Enriz, Ricardo DanielCobo, Justo4-Amino-5-(aminomethyl)pyrimidinesMicrowave irradiation; ; ; cyclocondensation;Theoretical calculationsAcid catalysisCyclocondensationStereoselectivityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Pyrimidine-5-carbaldehyde derivatives, of easy access, were selected as precursors for the synthesis of mimic pteridine derivatives 5,6-dihydropyrimido[4,5-d]pyrimidines and 5,6,7,8- tetrahydropyrimido[4,5-d]pyrimidines via 4-amino-(5-aminomethyl)pyrimidine intermediates. Straightforward procedures allow a quick access to these compounds. The dihydro derivatives were prepared means of a final cyclocondensation carried out with orthoesters, catalysed by acid and assisted by microwaves irradiation under solvent free conditions. The final cyclocondensation with carbonyl compounds forming the tetrahydro derivatives was done under mild conditions, in which stereochemical induction was carried out on the building of this skeleton, and stereochemistry assignments corroborated by theoretical calculations.Fil: de la Torre, José M.. Universidad de Jaén; EspañaFil: Nogueras, Manuel. Universidad de Jaén; EspañaFil: Borkowski, Eduardo Jorge. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Suvire, Fernando D.. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; ArgentinaFil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Cobo, Justo. Universidad de Jaén; EspañaArkat USA2014-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/14627de la Torre, José M.; Nogueras, Manuel; Borkowski, Eduardo Jorge; Suvire, Fernando D.; Enriz, Ricardo Daniel; et al.; Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes; Arkat USA; Arkivoc - Archive for Organic Chemistry; 2014; 5; 4-2014; 42-631551-70041551-7012enginfo:eu-repo/semantics/altIdentifier/url/http://quod.lib.umich.edu/a/ark/5550190.p008.653/1info:eu-repo/semantics/altIdentifier/url/http://dx.doi.org/10.3998/ark.5550190.p008.653info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:40:53Zoai:ri.conicet.gov.ar:11336/14627instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:40:54.128CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes
title Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes
spellingShingle Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes
de la Torre, José M.
4-Amino-5-(aminomethyl)pyrimidines
Microwave irradiation; ; ; cyclocondensation;
Theoretical calculations
Acid catalysis
Cyclocondensation
Stereoselectivity
title_short Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes
title_full Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes
title_fullStr Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes
title_full_unstemmed Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes
title_sort Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes
dc.creator.none.fl_str_mv de la Torre, José M.
Nogueras, Manuel
Borkowski, Eduardo Jorge
Suvire, Fernando D.
Enriz, Ricardo Daniel
Cobo, Justo
author de la Torre, José M.
author_facet de la Torre, José M.
Nogueras, Manuel
Borkowski, Eduardo Jorge
Suvire, Fernando D.
Enriz, Ricardo Daniel
Cobo, Justo
author_role author
author2 Nogueras, Manuel
Borkowski, Eduardo Jorge
Suvire, Fernando D.
Enriz, Ricardo Daniel
Cobo, Justo
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv 4-Amino-5-(aminomethyl)pyrimidines
Microwave irradiation; ; ; cyclocondensation;
Theoretical calculations
Acid catalysis
Cyclocondensation
Stereoselectivity
topic 4-Amino-5-(aminomethyl)pyrimidines
Microwave irradiation; ; ; cyclocondensation;
Theoretical calculations
Acid catalysis
Cyclocondensation
Stereoselectivity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Pyrimidine-5-carbaldehyde derivatives, of easy access, were selected as precursors for the synthesis of mimic pteridine derivatives 5,6-dihydropyrimido[4,5-d]pyrimidines and 5,6,7,8- tetrahydropyrimido[4,5-d]pyrimidines via 4-amino-(5-aminomethyl)pyrimidine intermediates. Straightforward procedures allow a quick access to these compounds. The dihydro derivatives were prepared means of a final cyclocondensation carried out with orthoesters, catalysed by acid and assisted by microwaves irradiation under solvent free conditions. The final cyclocondensation with carbonyl compounds forming the tetrahydro derivatives was done under mild conditions, in which stereochemical induction was carried out on the building of this skeleton, and stereochemistry assignments corroborated by theoretical calculations.
Fil: de la Torre, José M.. Universidad de Jaén; España
Fil: Nogueras, Manuel. Universidad de Jaén; España
Fil: Borkowski, Eduardo Jorge. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Suvire, Fernando D.. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Cobo, Justo. Universidad de Jaén; España
description Pyrimidine-5-carbaldehyde derivatives, of easy access, were selected as precursors for the synthesis of mimic pteridine derivatives 5,6-dihydropyrimido[4,5-d]pyrimidines and 5,6,7,8- tetrahydropyrimido[4,5-d]pyrimidines via 4-amino-(5-aminomethyl)pyrimidine intermediates. Straightforward procedures allow a quick access to these compounds. The dihydro derivatives were prepared means of a final cyclocondensation carried out with orthoesters, catalysed by acid and assisted by microwaves irradiation under solvent free conditions. The final cyclocondensation with carbonyl compounds forming the tetrahydro derivatives was done under mild conditions, in which stereochemical induction was carried out on the building of this skeleton, and stereochemistry assignments corroborated by theoretical calculations.
publishDate 2014
dc.date.none.fl_str_mv 2014-04
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/14627
de la Torre, José M.; Nogueras, Manuel; Borkowski, Eduardo Jorge; Suvire, Fernando D.; Enriz, Ricardo Daniel; et al.; Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes; Arkat USA; Arkivoc - Archive for Organic Chemistry; 2014; 5; 4-2014; 42-63
1551-7004
1551-7012
url http://hdl.handle.net/11336/14627
identifier_str_mv de la Torre, José M.; Nogueras, Manuel; Borkowski, Eduardo Jorge; Suvire, Fernando D.; Enriz, Ricardo Daniel; et al.; Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes; Arkat USA; Arkivoc - Archive for Organic Chemistry; 2014; 5; 4-2014; 42-63
1551-7004
1551-7012
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://quod.lib.umich.edu/a/ark/5550190.p008.653/1
info:eu-repo/semantics/altIdentifier/url/http://dx.doi.org/10.3998/ark.5550190.p008.653
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Arkat USA
publisher.none.fl_str_mv Arkat USA
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1844613294024818688
score 13.070432

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