A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocine...

Autores
Ramirez, Maria de Los Angeles; Ortiz, Mariela Gisela; Salerno, Alejandra; Perillo, Isabel Amalia; Blanco, María de Las Mercedes
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work, we describe the synthesis of a series of 1,2,3-trisubstituted-1,4,5,6,7,8-hexahydro-1,3-diazocinium salts (1) by alkylation of the corresponding 1,2-diaryl-1,4,5,6,7,8-hexahydro-1,3-diazocines (2). Compounds 2 were obtained by ethyl polyphosphate-promoted cyclocondensation of N-aroyl-N0-arylpentamethylenediamines (3). Reaction of compounds 2 with alkyl iodides led to 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium iodides (1), a new family of cyclic amidinium salts. The best yields for the alkylation were achieved using a mixture of DCM–DMSO (10:1) as solvent. The reaction times of both, the cyclocondensation of compounds 3 and the reaction of 2 with alkyl halides, are dramatically decreased when using microwave irradiation.
Fil: Ramirez, Maria de Los Angeles. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Ortiz, Mariela Gisela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Salerno, Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Perillo, Isabel Amalia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Blanco, María de Las Mercedes. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Materia
Cyclic amidinium salts
Cyclic amidines
Ethyl polyphosphate
N-alkylation
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:11336/106987
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/106987
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocinesRamirez, Maria de Los AngelesOrtiz, Mariela GiselaSalerno, AlejandraPerillo, Isabel AmaliaBlanco, María de Las MercedesCyclic amidinium saltsCyclic amidinesEthyl polyphosphateN-alkylationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this work, we describe the synthesis of a series of 1,2,3-trisubstituted-1,4,5,6,7,8-hexahydro-1,3-diazocinium salts (1) by alkylation of the corresponding 1,2-diaryl-1,4,5,6,7,8-hexahydro-1,3-diazocines (2). Compounds 2 were obtained by ethyl polyphosphate-promoted cyclocondensation of N-aroyl-N0-arylpentamethylenediamines (3). Reaction of compounds 2 with alkyl iodides led to 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium iodides (1), a new family of cyclic amidinium salts. The best yields for the alkylation were achieved using a mixture of DCM–DMSO (10:1) as solvent. The reaction times of both, the cyclocondensation of compounds 3 and the reaction of 2 with alkyl halides, are dramatically decreased when using microwave irradiation.Fil: Ramirez, Maria de Los Angeles. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Ortiz, Mariela Gisela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Salerno, Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Perillo, Isabel Amalia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Blanco, María de Las Mercedes. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaPergamon-Elsevier Science Ltd2012-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/106987Ramirez, Maria de Los Angeles; Ortiz, Mariela Gisela; Salerno, Alejandra; Perillo, Isabel Amalia; Blanco, María de Las Mercedes; A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 53; 11; 3-2012; 1367-13690040-4039CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403912000330info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2012.01.009info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-17T10:58:44Zoai:ri.conicet.gov.ar:11336/106987instacron: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:34982025-09-17 10:58:44.857CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines
title A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines
spellingShingle A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines
Ramirez, Maria de Los Angeles
Cyclic amidinium salts
Cyclic amidines
Ethyl polyphosphate
N-alkylation
title_short A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines
title_full A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines
title_fullStr A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines
title_full_unstemmed A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines
title_sort A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines
dc.creator.none.fl_str_mv Ramirez, Maria de Los Angeles
Ortiz, Mariela Gisela
Salerno, Alejandra
Perillo, Isabel Amalia
Blanco, María de Las Mercedes
author Ramirez, Maria de Los Angeles
author_facet Ramirez, Maria de Los Angeles
Ortiz, Mariela Gisela
Salerno, Alejandra
Perillo, Isabel Amalia
Blanco, María de Las Mercedes
author_role author
author2 Ortiz, Mariela Gisela
Salerno, Alejandra
Perillo, Isabel Amalia
Blanco, María de Las Mercedes
author2_role author
author
author
author
dc.subject.none.fl_str_mv Cyclic amidinium salts
Cyclic amidines
Ethyl polyphosphate
N-alkylation
topic Cyclic amidinium salts
Cyclic amidines
Ethyl polyphosphate
N-alkylation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this work, we describe the synthesis of a series of 1,2,3-trisubstituted-1,4,5,6,7,8-hexahydro-1,3-diazocinium salts (1) by alkylation of the corresponding 1,2-diaryl-1,4,5,6,7,8-hexahydro-1,3-diazocines (2). Compounds 2 were obtained by ethyl polyphosphate-promoted cyclocondensation of N-aroyl-N0-arylpentamethylenediamines (3). Reaction of compounds 2 with alkyl iodides led to 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium iodides (1), a new family of cyclic amidinium salts. The best yields for the alkylation were achieved using a mixture of DCM–DMSO (10:1) as solvent. The reaction times of both, the cyclocondensation of compounds 3 and the reaction of 2 with alkyl halides, are dramatically decreased when using microwave irradiation.
Fil: Ramirez, Maria de Los Angeles. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Ortiz, Mariela Gisela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Salerno, Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Perillo, Isabel Amalia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Blanco, María de Las Mercedes. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
description In this work, we describe the synthesis of a series of 1,2,3-trisubstituted-1,4,5,6,7,8-hexahydro-1,3-diazocinium salts (1) by alkylation of the corresponding 1,2-diaryl-1,4,5,6,7,8-hexahydro-1,3-diazocines (2). Compounds 2 were obtained by ethyl polyphosphate-promoted cyclocondensation of N-aroyl-N0-arylpentamethylenediamines (3). Reaction of compounds 2 with alkyl iodides led to 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium iodides (1), a new family of cyclic amidinium salts. The best yields for the alkylation were achieved using a mixture of DCM–DMSO (10:1) as solvent. The reaction times of both, the cyclocondensation of compounds 3 and the reaction of 2 with alkyl halides, are dramatically decreased when using microwave irradiation.
publishDate 2012
dc.date.none.fl_str_mv 2012-03
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/11336/106987
Ramirez, Maria de Los Angeles; Ortiz, Mariela Gisela; Salerno, Alejandra; Perillo, Isabel Amalia; Blanco, María de Las Mercedes; A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 53; 11; 3-2012; 1367-1369
0040-4039
CONICET Digital
CONICET
url http://hdl.handle.net/11336/106987
identifier_str_mv Ramirez, Maria de Los Angeles; Ortiz, Mariela Gisela; Salerno, Alejandra; Perillo, Isabel Amalia; Blanco, María de Las Mercedes; A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 53; 11; 3-2012; 1367-1369
0040-4039
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403912000330
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2012.01.009
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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 13.001348

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