Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates

Autores
Rodriguez, Juan Bautista
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including strong nucleophiles, such as organometallic reagents and enolates, as well as very mild nucleophiles, such as amines, mercaptans and alcohols. The title compound also possesses the ability to behave as a dipolarophile or dienophile in 1,3-dipolar cycloadditions or Diels–Alder reactions, giving rise to five- or six-membered rings containing the bisphosphonic unit. In summary, tetraethyl vinylidenebisphosphonate is a very useful synthon to have at hand for straightforward syntheses of bisphosphonate derivatives of diverse structures. This bisphosphonate moiety has proven to be very important to impart important pharmacological action.
Fil: Rodriguez, Juan Bautista. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Materia
Bisphosphonates
Michael Addition
1,3-Dipolar Cycloaddition
Diels-Alder Reaction
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:11336/18678
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of BisphosphonatesRodriguez, Juan BautistaBisphosphonatesMichael Addition1,3-Dipolar CycloadditionDiels-Alder Reactionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including strong nucleophiles, such as organometallic reagents and enolates, as well as very mild nucleophiles, such as amines, mercaptans and alcohols. The title compound also possesses the ability to behave as a dipolarophile or dienophile in 1,3-dipolar cycloadditions or Diels–Alder reactions, giving rise to five- or six-membered rings containing the bisphosphonic unit. In summary, tetraethyl vinylidenebisphosphonate is a very useful synthon to have at hand for straightforward syntheses of bisphosphonate derivatives of diverse structures. This bisphosphonate moiety has proven to be very important to impart important pharmacological action.Fil: Rodriguez, Juan Bautista. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaGeorg Thieme Verlag Kg2014-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/18678Rodriguez, Juan Bautista; Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates; Georg Thieme Verlag Kg; Synthesis-stuttgart; 46; 9; 4-2014; 1129-11420039-7881CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1055/s-0033-1340952info:eu-repo/semantics/altIdentifier/url/https://www.thieme-connect.de/DOI/DOI?10.1055/s-0033-1340952info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:39:27Zoai:ri.conicet.gov.ar:11336/18678instacron: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 10:39:27.483CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates
title Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates
spellingShingle Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates
Rodriguez, Juan Bautista
Bisphosphonates
Michael Addition
1,3-Dipolar Cycloaddition
Diels-Alder Reaction
title_short Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates
title_full Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates
title_fullStr Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates
title_full_unstemmed Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates
title_sort Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates
dc.creator.none.fl_str_mv Rodriguez, Juan Bautista
author Rodriguez, Juan Bautista
author_facet Rodriguez, Juan Bautista
author_role author
dc.subject.none.fl_str_mv Bisphosphonates
Michael Addition
1,3-Dipolar Cycloaddition
Diels-Alder Reaction
topic Bisphosphonates
Michael Addition
1,3-Dipolar Cycloaddition
Diels-Alder Reaction
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including strong nucleophiles, such as organometallic reagents and enolates, as well as very mild nucleophiles, such as amines, mercaptans and alcohols. The title compound also possesses the ability to behave as a dipolarophile or dienophile in 1,3-dipolar cycloadditions or Diels–Alder reactions, giving rise to five- or six-membered rings containing the bisphosphonic unit. In summary, tetraethyl vinylidenebisphosphonate is a very useful synthon to have at hand for straightforward syntheses of bisphosphonate derivatives of diverse structures. This bisphosphonate moiety has proven to be very important to impart important pharmacological action.
Fil: Rodriguez, Juan Bautista. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
description Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including strong nucleophiles, such as organometallic reagents and enolates, as well as very mild nucleophiles, such as amines, mercaptans and alcohols. The title compound also possesses the ability to behave as a dipolarophile or dienophile in 1,3-dipolar cycloadditions or Diels–Alder reactions, giving rise to five- or six-membered rings containing the bisphosphonic unit. In summary, tetraethyl vinylidenebisphosphonate is a very useful synthon to have at hand for straightforward syntheses of bisphosphonate derivatives of diverse structures. This bisphosphonate moiety has proven to be very important to impart important pharmacological action.
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/11336/18678
Rodriguez, Juan Bautista; Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates; Georg Thieme Verlag Kg; Synthesis-stuttgart; 46; 9; 4-2014; 1129-1142
0039-7881
CONICET Digital
CONICET
url http://hdl.handle.net/11336/18678
identifier_str_mv Rodriguez, Juan Bautista; Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates; Georg Thieme Verlag Kg; Synthesis-stuttgart; 46; 9; 4-2014; 1129-1142
0039-7881
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1055/s-0033-1340952
info:eu-repo/semantics/altIdentifier/url/https://www.thieme-connect.de/DOI/DOI?10.1055/s-0033-1340952
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 Georg Thieme Verlag Kg
publisher.none.fl_str_mv Georg Thieme Verlag Kg
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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