Reaction of isatin with alkylating agents with acidic methylenes

Autores
Shmidt, María Sol; Perillo, Isabel Amalia; González, Mercedes; Blanco, María de Las Mercedes
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solventsleads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads tocompetitive formation of the corresponding epoxide 5. The formation of 5 is favored by low-polarity solvents at low temperatures and strong bases. Epoxides 5c, d obtained using NaEtOH/EtOH at 0?5 C are transformed into the corresponding 4-quinolinones 6 at higher temperatures. The use of Ag2CO3 allows obtaining compounds 3 as major products, along with varying amounts of labile O-alkyl derivatives 4 and dimerization products.
Fil: Shmidt, María Sol. 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: Perillo, Isabel Amalia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: González, Mercedes. Universidad de la República. Facultad de Ciencias; Uruguay
Fil: Blanco, María de Las Mercedes. 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
Materia
4-QUINOLINONES
EPOXYOXINDOLES
ISATIN
N- AND O-ALKYL DERIVATIVES
REARRANGEMENT
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:11336/198422
Acceder
id CONICETDig_f0edc29041c20563151a3ccb4c554c87
oai_identifier_str oai:ri.conicet.gov.ar:11336/198422
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Reaction of isatin with alkylating agents with acidic methylenesShmidt, María SolPerillo, Isabel AmaliaGonzález, MercedesBlanco, María de Las Mercedes4-QUINOLINONESEPOXYOXINDOLESISATINN- AND O-ALKYL DERIVATIVESREARRANGEMENThttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solventsleads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads tocompetitive formation of the corresponding epoxide 5. The formation of 5 is favored by low-polarity solvents at low temperatures and strong bases. Epoxides 5c, d obtained using NaEtOH/EtOH at 0?5 C are transformed into the corresponding 4-quinolinones 6 at higher temperatures. The use of Ag2CO3 allows obtaining compounds 3 as major products, along with varying amounts of labile O-alkyl derivatives 4 and dimerization products.Fil: Shmidt, María Sol. 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: Perillo, Isabel Amalia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: González, Mercedes. Universidad de la República. Facultad de Ciencias; UruguayFil: Blanco, María de Las Mercedes. 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; ArgentinaPergamon-Elsevier Science Ltd2012-05info: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/11336/198422Shmidt, María Sol; Perillo, Isabel Amalia; González, Mercedes; Blanco, María de Las Mercedes; Reaction of isatin with alkylating agents with acidic methylenes; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 53; 20; 5-2012; 2514-25170040-4039CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040403912003887info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2012.03.010info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:17:44Zoai:ri.conicet.gov.ar:11336/198422instacron: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:34982025-09-10 13:17:44.519CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Reaction of isatin with alkylating agents with acidic methylenes
title Reaction of isatin with alkylating agents with acidic methylenes
spellingShingle Reaction of isatin with alkylating agents with acidic methylenes
Shmidt, María Sol
4-QUINOLINONES
EPOXYOXINDOLES
ISATIN
N- AND O-ALKYL DERIVATIVES
REARRANGEMENT
title_short Reaction of isatin with alkylating agents with acidic methylenes
title_full Reaction of isatin with alkylating agents with acidic methylenes
title_fullStr Reaction of isatin with alkylating agents with acidic methylenes
title_full_unstemmed Reaction of isatin with alkylating agents with acidic methylenes
title_sort Reaction of isatin with alkylating agents with acidic methylenes
dc.creator.none.fl_str_mv Shmidt, María Sol
Perillo, Isabel Amalia
González, Mercedes
Blanco, María de Las Mercedes
author Shmidt, María Sol
author_facet Shmidt, María Sol
Perillo, Isabel Amalia
González, Mercedes
Blanco, María de Las Mercedes
author_role author
author2 Perillo, Isabel Amalia
González, Mercedes
Blanco, María de Las Mercedes
author2_role author
author
author
dc.subject.none.fl_str_mv 4-QUINOLINONES
EPOXYOXINDOLES
ISATIN
N- AND O-ALKYL DERIVATIVES
REARRANGEMENT
topic 4-QUINOLINONES
EPOXYOXINDOLES
ISATIN
N- AND O-ALKYL DERIVATIVES
REARRANGEMENT
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solventsleads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads tocompetitive formation of the corresponding epoxide 5. The formation of 5 is favored by low-polarity solvents at low temperatures and strong bases. Epoxides 5c, d obtained using NaEtOH/EtOH at 0?5 C are transformed into the corresponding 4-quinolinones 6 at higher temperatures. The use of Ag2CO3 allows obtaining compounds 3 as major products, along with varying amounts of labile O-alkyl derivatives 4 and dimerization products.
Fil: Shmidt, María Sol. 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: Perillo, Isabel Amalia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: González, Mercedes. Universidad de la República. Facultad de Ciencias; Uruguay
Fil: Blanco, María de Las Mercedes. 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
description The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solventsleads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads tocompetitive formation of the corresponding epoxide 5. The formation of 5 is favored by low-polarity solvents at low temperatures and strong bases. Epoxides 5c, d obtained using NaEtOH/EtOH at 0?5 C are transformed into the corresponding 4-quinolinones 6 at higher temperatures. The use of Ag2CO3 allows obtaining compounds 3 as major products, along with varying amounts of labile O-alkyl derivatives 4 and dimerization products.
publishDate 2012
dc.date.none.fl_str_mv 2012-05
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/11336/198422
Shmidt, María Sol; Perillo, Isabel Amalia; González, Mercedes; Blanco, María de Las Mercedes; Reaction of isatin with alkylating agents with acidic methylenes; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 53; 20; 5-2012; 2514-2517
0040-4039
CONICET Digital
CONICET
url http://hdl.handle.net/11336/198422
identifier_str_mv Shmidt, María Sol; Perillo, Isabel Amalia; González, Mercedes; Blanco, María de Las Mercedes; Reaction of isatin with alkylating agents with acidic methylenes; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 53; 20; 5-2012; 2514-2517
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/S0040403912003887
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2012.03.010
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
_version_ 1842980968547221504
score 12.993085

Publicaciones similares