Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate

Autores
Méndez, María Virginia; Heredia, Daniel Alejandro; Larghi, Enrique Leandro; Bracca, Andrea Beatriz Juana; Kaufman, Teodoro Saul
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A convenient approach toward the indoloquinolines neocryptolepine and 6-methylquinindoline from a common intermediate, is reported. Both sequences, designed for maximum use of accessible reagents and robust conditions, are straightforward and efficient. They involved the amidation of 2-aminobenzaldehyde (prepared by iron-mediated reduction of 2-nitrobenzaldehyde) with 2-nitrophenylacetic acid, followed by a K2CO3-assisted cyclization to form a 3-(2-nitrophenyl)quinolin-2-one as the common precursor. Me2CO3-mediated N-methylation of the lactam, reduction of the nitro moiety and final cyclization resulted in 55% overall yield of neocryptolepine, whereas cyclocondensation and N-methylation afforded 79% overall yield of 6-methyl quinindoline. Thus, the sequences toward the targets entailed two POCl3-promoted C-N bond forming reactions, two Fe-mediated nitro group reductions and two base-promoted transformations.
Fil: Méndez, María Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Heredia, Daniel Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Bracca, Andrea Beatriz Juana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
NEOCRYPTOLEPINE
6-METHYLQUININDOLINE
TOTAL SYNTHESIS
HETEROCYCLES
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:11336/50447
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/50447
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediateMéndez, María VirginiaHeredia, Daniel AlejandroLarghi, Enrique LeandroBracca, Andrea Beatriz JuanaKaufman, Teodoro SaulNEOCRYPTOLEPINE6-METHYLQUININDOLINETOTAL SYNTHESISHETEROCYCLEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A convenient approach toward the indoloquinolines neocryptolepine and 6-methylquinindoline from a common intermediate, is reported. Both sequences, designed for maximum use of accessible reagents and robust conditions, are straightforward and efficient. They involved the amidation of 2-aminobenzaldehyde (prepared by iron-mediated reduction of 2-nitrobenzaldehyde) with 2-nitrophenylacetic acid, followed by a K2CO3-assisted cyclization to form a 3-(2-nitrophenyl)quinolin-2-one as the common precursor. Me2CO3-mediated N-methylation of the lactam, reduction of the nitro moiety and final cyclization resulted in 55% overall yield of neocryptolepine, whereas cyclocondensation and N-methylation afforded 79% overall yield of 6-methyl quinindoline. Thus, the sequences toward the targets entailed two POCl3-promoted C-N bond forming reactions, two Fe-mediated nitro group reductions and two base-promoted transformations.Fil: Méndez, María Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Heredia, Daniel Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Bracca, Andrea Beatriz Juana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaRoyal Society of Chemistry2017-05info: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/11336/50447Méndez, María Virginia; Heredia, Daniel Alejandro; Larghi, Enrique Leandro; Bracca, Andrea Beatriz Juana; Kaufman, Teodoro Saul; Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate; Royal Society of Chemistry; RSC Advances; 7; 45; 5-2017; 28298-283072046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/C7RA05349Einfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2017/RA/C7RA05349Einfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:45:28Zoai:ri.conicet.gov.ar:11336/50447instacron: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:34982025-09-03 09:45:29.003CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
title Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
spellingShingle Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
Méndez, María Virginia
NEOCRYPTOLEPINE
6-METHYLQUININDOLINE
TOTAL SYNTHESIS
HETEROCYCLES
title_short Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
title_full Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
title_fullStr Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
title_full_unstemmed Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
title_sort Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate
dc.creator.none.fl_str_mv Méndez, María Virginia
Heredia, Daniel Alejandro
Larghi, Enrique Leandro
Bracca, Andrea Beatriz Juana
Kaufman, Teodoro Saul
author Méndez, María Virginia
author_facet Méndez, María Virginia
Heredia, Daniel Alejandro
Larghi, Enrique Leandro
Bracca, Andrea Beatriz Juana
Kaufman, Teodoro Saul
author_role author
author2 Heredia, Daniel Alejandro
Larghi, Enrique Leandro
Bracca, Andrea Beatriz Juana
Kaufman, Teodoro Saul
author2_role author
author
author
author
dc.subject.none.fl_str_mv NEOCRYPTOLEPINE
6-METHYLQUININDOLINE
TOTAL SYNTHESIS
HETEROCYCLES
topic NEOCRYPTOLEPINE
6-METHYLQUININDOLINE
TOTAL SYNTHESIS
HETEROCYCLES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A convenient approach toward the indoloquinolines neocryptolepine and 6-methylquinindoline from a common intermediate, is reported. Both sequences, designed for maximum use of accessible reagents and robust conditions, are straightforward and efficient. They involved the amidation of 2-aminobenzaldehyde (prepared by iron-mediated reduction of 2-nitrobenzaldehyde) with 2-nitrophenylacetic acid, followed by a K2CO3-assisted cyclization to form a 3-(2-nitrophenyl)quinolin-2-one as the common precursor. Me2CO3-mediated N-methylation of the lactam, reduction of the nitro moiety and final cyclization resulted in 55% overall yield of neocryptolepine, whereas cyclocondensation and N-methylation afforded 79% overall yield of 6-methyl quinindoline. Thus, the sequences toward the targets entailed two POCl3-promoted C-N bond forming reactions, two Fe-mediated nitro group reductions and two base-promoted transformations.
Fil: Méndez, María Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Heredia, Daniel Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Bracca, Andrea Beatriz Juana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description A convenient approach toward the indoloquinolines neocryptolepine and 6-methylquinindoline from a common intermediate, is reported. Both sequences, designed for maximum use of accessible reagents and robust conditions, are straightforward and efficient. They involved the amidation of 2-aminobenzaldehyde (prepared by iron-mediated reduction of 2-nitrobenzaldehyde) with 2-nitrophenylacetic acid, followed by a K2CO3-assisted cyclization to form a 3-(2-nitrophenyl)quinolin-2-one as the common precursor. Me2CO3-mediated N-methylation of the lactam, reduction of the nitro moiety and final cyclization resulted in 55% overall yield of neocryptolepine, whereas cyclocondensation and N-methylation afforded 79% overall yield of 6-methyl quinindoline. Thus, the sequences toward the targets entailed two POCl3-promoted C-N bond forming reactions, two Fe-mediated nitro group reductions and two base-promoted transformations.
publishDate 2017
dc.date.none.fl_str_mv 2017-05
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/11336/50447
Méndez, María Virginia; Heredia, Daniel Alejandro; Larghi, Enrique Leandro; Bracca, Andrea Beatriz Juana; Kaufman, Teodoro Saul; Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate; Royal Society of Chemistry; RSC Advances; 7; 45; 5-2017; 28298-28307
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/50447
identifier_str_mv Méndez, María Virginia; Heredia, Daniel Alejandro; Larghi, Enrique Leandro; Bracca, Andrea Beatriz Juana; Kaufman, Teodoro Saul; Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate; Royal Society of Chemistry; RSC Advances; 7; 45; 5-2017; 28298-28307
2046-2069
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/C7RA05349E
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2017/RA/C7RA05349E
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 Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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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