Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine

Autores
Díaz, Jimena Estela; Ranieri, Silvia; Gruber, Nadia; Orelli, Liliana Raquel
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A straightforward strategy for the synthesis of dihydroquinazolines is presented, which allows for the preparation of 3,4- and 1,4-dihydroquinazolines with different substitution patterns from 2-aminobenzylamine (2-ABA) as common precursor. The required functionalization of both amino groups present in 2-ABA was achieved by different routes involving selective N-acylation and cesium carbonate mediated N-alkylation reactions, avoiding protection/deprotection steps. The heterocycles were efficiently synthesized in short reaction times by microwave-assisted ring closure of the corresponding aminoamides promoted by ethyl polyphosphate (PPE).
Fil: Díaz, Jimena Estela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Ranieri, Silvia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Universita Degli Studi Di Bologna; Italia
Fil: Gruber, Nadia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Orelli, Liliana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Materia
Dihydroquinazolines
N-alkylations
N-acylations
Microwaves
PPE
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/49091
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamineDíaz, Jimena EstelaRanieri, SilviaGruber, NadiaOrelli, Liliana RaquelDihydroquinazolinesN-alkylationsN-acylationsMicrowavesPPEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A straightforward strategy for the synthesis of dihydroquinazolines is presented, which allows for the preparation of 3,4- and 1,4-dihydroquinazolines with different substitution patterns from 2-aminobenzylamine (2-ABA) as common precursor. The required functionalization of both amino groups present in 2-ABA was achieved by different routes involving selective N-acylation and cesium carbonate mediated N-alkylation reactions, avoiding protection/deprotection steps. The heterocycles were efficiently synthesized in short reaction times by microwave-assisted ring closure of the corresponding aminoamides promoted by ethyl polyphosphate (PPE).Fil: Díaz, Jimena Estela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Ranieri, Silvia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Universita Degli Studi Di Bologna; ItaliaFil: Gruber, Nadia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Orelli, Liliana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaBeilstein-Institut2017-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/49091Díaz, Jimena Estela; Ranieri, Silvia; Gruber, Nadia; Orelli, Liliana Raquel; Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine; Beilstein-Institut; Beilstein Journal Of Organic Chemistry; 13; 6-2017; 1470-14771860-5397CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5550820/info:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.13.145info:eu-repo/semantics/altIdentifier/url/https://www.beilstein-journals.org/bjoc/articles/13/145info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:24:47Zoai:ri.conicet.gov.ar:11336/49091instacron: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 10:24:47.295CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine
title Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine
spellingShingle Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine
Díaz, Jimena Estela
Dihydroquinazolines
N-alkylations
N-acylations
Microwaves
PPE
title_short Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine
title_full Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine
title_fullStr Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine
title_full_unstemmed Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine
title_sort Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine
dc.creator.none.fl_str_mv Díaz, Jimena Estela
Ranieri, Silvia
Gruber, Nadia
Orelli, Liliana Raquel
author Díaz, Jimena Estela
author_facet Díaz, Jimena Estela
Ranieri, Silvia
Gruber, Nadia
Orelli, Liliana Raquel
author_role author
author2 Ranieri, Silvia
Gruber, Nadia
Orelli, Liliana Raquel
author2_role author
author
author
dc.subject.none.fl_str_mv Dihydroquinazolines
N-alkylations
N-acylations
Microwaves
PPE
topic Dihydroquinazolines
N-alkylations
N-acylations
Microwaves
PPE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A straightforward strategy for the synthesis of dihydroquinazolines is presented, which allows for the preparation of 3,4- and 1,4-dihydroquinazolines with different substitution patterns from 2-aminobenzylamine (2-ABA) as common precursor. The required functionalization of both amino groups present in 2-ABA was achieved by different routes involving selective N-acylation and cesium carbonate mediated N-alkylation reactions, avoiding protection/deprotection steps. The heterocycles were efficiently synthesized in short reaction times by microwave-assisted ring closure of the corresponding aminoamides promoted by ethyl polyphosphate (PPE).
Fil: Díaz, Jimena Estela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Ranieri, Silvia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Universita Degli Studi Di Bologna; Italia
Fil: Gruber, Nadia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Orelli, Liliana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
description A straightforward strategy for the synthesis of dihydroquinazolines is presented, which allows for the preparation of 3,4- and 1,4-dihydroquinazolines with different substitution patterns from 2-aminobenzylamine (2-ABA) as common precursor. The required functionalization of both amino groups present in 2-ABA was achieved by different routes involving selective N-acylation and cesium carbonate mediated N-alkylation reactions, avoiding protection/deprotection steps. The heterocycles were efficiently synthesized in short reaction times by microwave-assisted ring closure of the corresponding aminoamides promoted by ethyl polyphosphate (PPE).
publishDate 2017
dc.date.none.fl_str_mv 2017-06
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/11336/49091
Díaz, Jimena Estela; Ranieri, Silvia; Gruber, Nadia; Orelli, Liliana Raquel; Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine; Beilstein-Institut; Beilstein Journal Of Organic Chemistry; 13; 6-2017; 1470-1477
1860-5397
CONICET Digital
CONICET
url http://hdl.handle.net/11336/49091
identifier_str_mv Díaz, Jimena Estela; Ranieri, Silvia; Gruber, Nadia; Orelli, Liliana Raquel; Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine; Beilstein-Institut; Beilstein Journal Of Organic Chemistry; 13; 6-2017; 1470-1477
1860-5397
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5550820/
info:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.13.145
info:eu-repo/semantics/altIdentifier/url/https://www.beilstein-journals.org/bjoc/articles/13/145
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Beilstein-Institut
publisher.none.fl_str_mv Beilstein-Institut
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
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score 13.070432

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