Microwave-enhanced synthesis of phosphonoacetamides
- Autores
- Gruber, Nadia; Mollo, María Cruz; Zani, Mariana; Orelli, Liliana Raquel
- Año de publicación
- 2012
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono) acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory yields only when a high excess of the reagent was employed.
Fil: Gruber, Nadia. 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: Mollo, María Cruz. 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: Zani, Mariana. 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. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina - Materia
-
MICHAELIS-ARBUZOV REACTION
MICROWAVES
PHOSPHONOACETAMIDES
PHOSPHORUS COMPOUNDS
SODIUM IODIDE - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/198551
Ver los metadatos del registro completo
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Microwave-enhanced synthesis of phosphonoacetamidesGruber, NadiaMollo, María CruzZani, MarianaOrelli, Liliana RaquelMICHAELIS-ARBUZOV REACTIONMICROWAVESPHOSPHONOACETAMIDESPHOSPHORUS COMPOUNDSSODIUM IODIDEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono) acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory yields only when a high excess of the reagent was employed.Fil: Gruber, Nadia. 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: Mollo, María Cruz. 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: Zani, Mariana. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Orelli, Liliana Raquel. 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; ArgentinaTaylor & Francis2012-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/198551Gruber, Nadia; Mollo, María Cruz; Zani, Mariana; Orelli, Liliana Raquel; Microwave-enhanced synthesis of phosphonoacetamides; Taylor & Francis; Synthetic Communications; 42; 5; 3-2012; 738-7460039-7911CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.tandfonline.com/doi/abs/10.1080/00397911.2010.530377info:eu-repo/semantics/altIdentifier/doi/10.1080/00397911.2010.530377info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:22:40Zoai:ri.conicet.gov.ar:11336/198551instacron: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 10:22:40.959CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Microwave-enhanced synthesis of phosphonoacetamides |
title |
Microwave-enhanced synthesis of phosphonoacetamides |
spellingShingle |
Microwave-enhanced synthesis of phosphonoacetamides Gruber, Nadia MICHAELIS-ARBUZOV REACTION MICROWAVES PHOSPHONOACETAMIDES PHOSPHORUS COMPOUNDS SODIUM IODIDE |
title_short |
Microwave-enhanced synthesis of phosphonoacetamides |
title_full |
Microwave-enhanced synthesis of phosphonoacetamides |
title_fullStr |
Microwave-enhanced synthesis of phosphonoacetamides |
title_full_unstemmed |
Microwave-enhanced synthesis of phosphonoacetamides |
title_sort |
Microwave-enhanced synthesis of phosphonoacetamides |
dc.creator.none.fl_str_mv |
Gruber, Nadia Mollo, María Cruz Zani, Mariana Orelli, Liliana Raquel |
author |
Gruber, Nadia |
author_facet |
Gruber, Nadia Mollo, María Cruz Zani, Mariana Orelli, Liliana Raquel |
author_role |
author |
author2 |
Mollo, María Cruz Zani, Mariana Orelli, Liliana Raquel |
author2_role |
author author author |
dc.subject.none.fl_str_mv |
MICHAELIS-ARBUZOV REACTION MICROWAVES PHOSPHONOACETAMIDES PHOSPHORUS COMPOUNDS SODIUM IODIDE |
topic |
MICHAELIS-ARBUZOV REACTION MICROWAVES PHOSPHONOACETAMIDES PHOSPHORUS COMPOUNDS SODIUM IODIDE |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono) acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory yields only when a high excess of the reagent was employed. Fil: Gruber, Nadia. 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: Mollo, María Cruz. 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: Zani, Mariana. 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. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina |
description |
An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono) acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory yields only when a high excess of the reagent was employed. |
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/11336/198551 Gruber, Nadia; Mollo, María Cruz; Zani, Mariana; Orelli, Liliana Raquel; Microwave-enhanced synthesis of phosphonoacetamides; Taylor & Francis; Synthetic Communications; 42; 5; 3-2012; 738-746 0039-7911 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/198551 |
identifier_str_mv |
Gruber, Nadia; Mollo, María Cruz; Zani, Mariana; Orelli, Liliana Raquel; Microwave-enhanced synthesis of phosphonoacetamides; Taylor & Francis; Synthetic Communications; 42; 5; 3-2012; 738-746 0039-7911 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.tandfonline.com/doi/abs/10.1080/00397911.2010.530377 info:eu-repo/semantics/altIdentifier/doi/10.1080/00397911.2010.530377 |
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 application/pdf |
dc.publisher.none.fl_str_mv |
Taylor & Francis |
publisher.none.fl_str_mv |
Taylor & Francis |
dc.source.none.fl_str_mv |
reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
reponame_str |
CONICET Digital (CONICET) |
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CONICET Digital (CONICET) |
instname_str |
Consejo Nacional de Investigaciones Científicas y Técnicas |
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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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1844614219178180608 |
score |
13.070432 |