1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives

Autores
Díaz, Jimena Estela; Bisceglia, Juan Angel; Mollo, María Cruz; Orelli, Liliana Raquel
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In the present Letter we report the use of N-arylputrescines as synthetic intermediates for the preparation of N-acyl-N′-aryltetramethylenediamines 3 and related seven-membered heterocyclic amidines 4. Compounds 1 were synthesized by Cs2CO3/KI-mediated aminolysis of 4-chlorobutyronitrile and subsequent reduction. N-Acylation of diamines 1 with carboxylic acid anhydrides led selectively to N-acyl-N′-aryl tetramethylenediamines 3. Microwave-assisted ring closure of such precursors promoted by PPE allowed for the synthesis of hitherto unreported 1-aryl-2-alkyl-1H-1,4,5,6-tetrahydro-1,3-diazepines 4. © 2011 Elsevier Ltd. All rights reserved.
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: Bisceglia, Juan Angel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Mollo, María Cruz. 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
Cyclic Amidines
Cyclodehydration
Microwaves
N-Acylation
Polyamines
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:11336/67271
Acceder
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network_name_str CONICET Digital (CONICET)
spelling 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivativesDíaz, Jimena EstelaBisceglia, Juan AngelMollo, María CruzOrelli, Liliana RaquelCyclic AmidinesCyclodehydrationMicrowavesN-AcylationPolyamineshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In the present Letter we report the use of N-arylputrescines as synthetic intermediates for the preparation of N-acyl-N′-aryltetramethylenediamines 3 and related seven-membered heterocyclic amidines 4. Compounds 1 were synthesized by Cs2CO3/KI-mediated aminolysis of 4-chlorobutyronitrile and subsequent reduction. N-Acylation of diamines 1 with carboxylic acid anhydrides led selectively to N-acyl-N′-aryl tetramethylenediamines 3. Microwave-assisted ring closure of such precursors promoted by PPE allowed for the synthesis of hitherto unreported 1-aryl-2-alkyl-1H-1,4,5,6-tetrahydro-1,3-diazepines 4. © 2011 Elsevier Ltd. All rights reserved.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: Bisceglia, Juan Angel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Mollo, María Cruz. 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; ArgentinaPergamon-Elsevier Science Ltd2011-04info: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/11336/67271Díaz, Jimena Estela; Bisceglia, Juan Angel; Mollo, María Cruz; Orelli, Liliana Raquel; 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 52; 16; 4-2011; 1895-18970040-4039CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040403911002632info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2011.02.042info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-17T11:34:27Zoai:ri.conicet.gov.ar:11336/67271instacron: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 11:34:27.788CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives
title 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives
spellingShingle 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives
Díaz, Jimena Estela
Cyclic Amidines
Cyclodehydration
Microwaves
N-Acylation
Polyamines
title_short 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives
title_full 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives
title_fullStr 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives
title_full_unstemmed 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives
title_sort 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives
dc.creator.none.fl_str_mv Díaz, Jimena Estela
Bisceglia, Juan Angel
Mollo, María Cruz
Orelli, Liliana Raquel
author Díaz, Jimena Estela
author_facet Díaz, Jimena Estela
Bisceglia, Juan Angel
Mollo, María Cruz
Orelli, Liliana Raquel
author_role author
author2 Bisceglia, Juan Angel
Mollo, María Cruz
Orelli, Liliana Raquel
author2_role author
author
author
dc.subject.none.fl_str_mv Cyclic Amidines
Cyclodehydration
Microwaves
N-Acylation
Polyamines
topic Cyclic Amidines
Cyclodehydration
Microwaves
N-Acylation
Polyamines
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 the present Letter we report the use of N-arylputrescines as synthetic intermediates for the preparation of N-acyl-N′-aryltetramethylenediamines 3 and related seven-membered heterocyclic amidines 4. Compounds 1 were synthesized by Cs2CO3/KI-mediated aminolysis of 4-chlorobutyronitrile and subsequent reduction. N-Acylation of diamines 1 with carboxylic acid anhydrides led selectively to N-acyl-N′-aryl tetramethylenediamines 3. Microwave-assisted ring closure of such precursors promoted by PPE allowed for the synthesis of hitherto unreported 1-aryl-2-alkyl-1H-1,4,5,6-tetrahydro-1,3-diazepines 4. © 2011 Elsevier Ltd. All rights reserved.
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: Bisceglia, Juan Angel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Mollo, María Cruz. 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 In the present Letter we report the use of N-arylputrescines as synthetic intermediates for the preparation of N-acyl-N′-aryltetramethylenediamines 3 and related seven-membered heterocyclic amidines 4. Compounds 1 were synthesized by Cs2CO3/KI-mediated aminolysis of 4-chlorobutyronitrile and subsequent reduction. N-Acylation of diamines 1 with carboxylic acid anhydrides led selectively to N-acyl-N′-aryl tetramethylenediamines 3. Microwave-assisted ring closure of such precursors promoted by PPE allowed for the synthesis of hitherto unreported 1-aryl-2-alkyl-1H-1,4,5,6-tetrahydro-1,3-diazepines 4. © 2011 Elsevier Ltd. All rights reserved.
publishDate 2011
dc.date.none.fl_str_mv 2011-04
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/11336/67271
Díaz, Jimena Estela; Bisceglia, Juan Angel; Mollo, María Cruz; Orelli, Liliana Raquel; 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 52; 16; 4-2011; 1895-1897
0040-4039
CONICET Digital
CONICET
url http://hdl.handle.net/11336/67271
identifier_str_mv Díaz, Jimena Estela; Bisceglia, Juan Angel; Mollo, María Cruz; Orelli, Liliana Raquel; 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 52; 16; 4-2011; 1895-1897
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/https://www.sciencedirect.com/science/article/pii/S0040403911002632
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2011.02.042
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
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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