Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts

Autores
Abonia, Rodrigo; Gutiérrez, Luisa F.; Insuasty, Braulio; Quiroga, Jairo; Laali, Kenneth K.; Zhao, Chunqing; Borosky, Gabriela Leonor; Horwitz, Samantha M.; Bunge, Scott D.
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of giant tris(heteroaryl)methanes are easily assembled by one-pot three-component synthesis by simple reflux in ethanol without catalyst or additives. Diversely substituted indoles (Ar1) react with quinoline aldehydes, quinolone aldehydes, chromone aldehydes, and fluorene aldehydes (Ar2CHO) and coumarins (Ar3) in 1:1:1 ratio to form the corresponding tris(heteroaryl)methanes (Ar1Ar2Ar3)CH along with (Ar1Ar1Ar2)CH triads. A series of new 2:1 triads were also synthesized by coupling substituted indoles with Ar2CHO. The coupling reactions could also be carried out in water (at circa 80 °C) but with chemoselectivity favoring (Ar1Ar1Ar2)CH over (Ar1Ar2Ar3)CH. The molecular structure of a representative (Ar1Ar2Ar3)CH triad was confirmed by X-ray analysis. Model tris(heteroaryl/aryl)methylium salts were generated by reaction with DDQ/HPF6 and studied by NMR and by DFT and GIAO-DFT.
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Gutiérrez, Luisa F.. University Of North Florida; Estados Unidos. Universidad del Valle; Colombia
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Fil: Laali, Kenneth K.. University Of North Florida; Estados Unidos
Fil: Zhao, Chunqing. University Of North Florida; Estados Unidos
Fil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Horwitz, Samantha M.. Kent State University; Estados Unidos
Fil: Bunge, Scott D.. Kent State University; Estados Unidos
Materia
MODEL HETEROARYLMETHYLIUM SALTS
MULTICOMPONENT
ONE-POT CATALYST-FREE ASSEMBLY
PHARMACOPHORIC TRIADS
THREE-COMPONEN SYNTHESIS
TRIS(HETEROARYL)METHANES
YONEMITSU-TYPE REACTION
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/125435
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/125435
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation saltsAbonia, RodrigoGutiérrez, Luisa F.Insuasty, BraulioQuiroga, JairoLaali, Kenneth K.Zhao, ChunqingBorosky, Gabriela LeonorHorwitz, Samantha M.Bunge, Scott D.MODEL HETEROARYLMETHYLIUM SALTSMULTICOMPONENTONE-POT CATALYST-FREE ASSEMBLYPHARMACOPHORIC TRIADSTHREE-COMPONEN SYNTHESISTRIS(HETEROARYL)METHANESYONEMITSU-TYPE REACTIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of giant tris(heteroaryl)methanes are easily assembled by one-pot three-component synthesis by simple reflux in ethanol without catalyst or additives. Diversely substituted indoles (Ar1) react with quinoline aldehydes, quinolone aldehydes, chromone aldehydes, and fluorene aldehydes (Ar2CHO) and coumarins (Ar3) in 1:1:1 ratio to form the corresponding tris(heteroaryl)methanes (Ar1Ar2Ar3)CH along with (Ar1Ar1Ar2)CH triads. A series of new 2:1 triads were also synthesized by coupling substituted indoles with Ar2CHO. The coupling reactions could also be carried out in water (at circa 80 °C) but with chemoselectivity favoring (Ar1Ar1Ar2)CH over (Ar1Ar2Ar3)CH. The molecular structure of a representative (Ar1Ar2Ar3)CH triad was confirmed by X-ray analysis. Model tris(heteroaryl/aryl)methylium salts were generated by reaction with DDQ/HPF6 and studied by NMR and by DFT and GIAO-DFT.Fil: Abonia, Rodrigo. Universidad del Valle; ColombiaFil: Gutiérrez, Luisa F.. University Of North Florida; Estados Unidos. Universidad del Valle; ColombiaFil: Insuasty, Braulio. Universidad del Valle; ColombiaFil: Quiroga, Jairo. Universidad del Valle; ColombiaFil: Laali, Kenneth K.. University Of North Florida; Estados UnidosFil: Zhao, Chunqing. University Of North Florida; Estados UnidosFil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Horwitz, Samantha M.. Kent State University; Estados UnidosFil: Bunge, Scott D.. Kent State University; Estados UnidosBeilstein-Institut2019-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/125435Abonia, Rodrigo; Gutiérrez, Luisa F.; Insuasty, Braulio; Quiroga, Jairo; Laali, Kenneth K.; et al.; Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts; Beilstein-Institut; Beilstein Journal Of Organic Chemistry; 15; 3-2019; 642-6541860-5397CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.15.60info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:43:10Zoai:ri.conicet.gov.ar:11336/125435instacron: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:34982025-10-15 14:43:10.535CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
title Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
spellingShingle Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
Abonia, Rodrigo
MODEL HETEROARYLMETHYLIUM SALTS
MULTICOMPONENT
ONE-POT CATALYST-FREE ASSEMBLY
PHARMACOPHORIC TRIADS
THREE-COMPONEN SYNTHESIS
TRIS(HETEROARYL)METHANES
YONEMITSU-TYPE REACTION
title_short Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
title_full Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
title_fullStr Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
title_full_unstemmed Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
title_sort Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
dc.creator.none.fl_str_mv Abonia, Rodrigo
Gutiérrez, Luisa F.
Insuasty, Braulio
Quiroga, Jairo
Laali, Kenneth K.
Zhao, Chunqing
Borosky, Gabriela Leonor
Horwitz, Samantha M.
Bunge, Scott D.
author Abonia, Rodrigo
author_facet Abonia, Rodrigo
Gutiérrez, Luisa F.
Insuasty, Braulio
Quiroga, Jairo
Laali, Kenneth K.
Zhao, Chunqing
Borosky, Gabriela Leonor
Horwitz, Samantha M.
Bunge, Scott D.
author_role author
author2 Gutiérrez, Luisa F.
Insuasty, Braulio
Quiroga, Jairo
Laali, Kenneth K.
Zhao, Chunqing
Borosky, Gabriela Leonor
Horwitz, Samantha M.
Bunge, Scott D.
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv MODEL HETEROARYLMETHYLIUM SALTS
MULTICOMPONENT
ONE-POT CATALYST-FREE ASSEMBLY
PHARMACOPHORIC TRIADS
THREE-COMPONEN SYNTHESIS
TRIS(HETEROARYL)METHANES
YONEMITSU-TYPE REACTION
topic MODEL HETEROARYLMETHYLIUM SALTS
MULTICOMPONENT
ONE-POT CATALYST-FREE ASSEMBLY
PHARMACOPHORIC TRIADS
THREE-COMPONEN SYNTHESIS
TRIS(HETEROARYL)METHANES
YONEMITSU-TYPE 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 A series of giant tris(heteroaryl)methanes are easily assembled by one-pot three-component synthesis by simple reflux in ethanol without catalyst or additives. Diversely substituted indoles (Ar1) react with quinoline aldehydes, quinolone aldehydes, chromone aldehydes, and fluorene aldehydes (Ar2CHO) and coumarins (Ar3) in 1:1:1 ratio to form the corresponding tris(heteroaryl)methanes (Ar1Ar2Ar3)CH along with (Ar1Ar1Ar2)CH triads. A series of new 2:1 triads were also synthesized by coupling substituted indoles with Ar2CHO. The coupling reactions could also be carried out in water (at circa 80 °C) but with chemoselectivity favoring (Ar1Ar1Ar2)CH over (Ar1Ar2Ar3)CH. The molecular structure of a representative (Ar1Ar2Ar3)CH triad was confirmed by X-ray analysis. Model tris(heteroaryl/aryl)methylium salts were generated by reaction with DDQ/HPF6 and studied by NMR and by DFT and GIAO-DFT.
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Gutiérrez, Luisa F.. University Of North Florida; Estados Unidos. Universidad del Valle; Colombia
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Fil: Laali, Kenneth K.. University Of North Florida; Estados Unidos
Fil: Zhao, Chunqing. University Of North Florida; Estados Unidos
Fil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Horwitz, Samantha M.. Kent State University; Estados Unidos
Fil: Bunge, Scott D.. Kent State University; Estados Unidos
description A series of giant tris(heteroaryl)methanes are easily assembled by one-pot three-component synthesis by simple reflux in ethanol without catalyst or additives. Diversely substituted indoles (Ar1) react with quinoline aldehydes, quinolone aldehydes, chromone aldehydes, and fluorene aldehydes (Ar2CHO) and coumarins (Ar3) in 1:1:1 ratio to form the corresponding tris(heteroaryl)methanes (Ar1Ar2Ar3)CH along with (Ar1Ar1Ar2)CH triads. A series of new 2:1 triads were also synthesized by coupling substituted indoles with Ar2CHO. The coupling reactions could also be carried out in water (at circa 80 °C) but with chemoselectivity favoring (Ar1Ar1Ar2)CH over (Ar1Ar2Ar3)CH. The molecular structure of a representative (Ar1Ar2Ar3)CH triad was confirmed by X-ray analysis. Model tris(heteroaryl/aryl)methylium salts were generated by reaction with DDQ/HPF6 and studied by NMR and by DFT and GIAO-DFT.
publishDate 2019
dc.date.none.fl_str_mv 2019-03
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/11336/125435
Abonia, Rodrigo; Gutiérrez, Luisa F.; Insuasty, Braulio; Quiroga, Jairo; Laali, Kenneth K.; et al.; Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts; Beilstein-Institut; Beilstein Journal Of Organic Chemistry; 15; 3-2019; 642-654
1860-5397
CONICET Digital
CONICET
url http://hdl.handle.net/11336/125435
identifier_str_mv Abonia, Rodrigo; Gutiérrez, Luisa F.; Insuasty, Braulio; Quiroga, Jairo; Laali, Kenneth K.; et al.; Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts; Beilstein-Institut; Beilstein Journal Of Organic Chemistry; 15; 3-2019; 642-654
1860-5397
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.15.60
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Beilstein-Institut
publisher.none.fl_str_mv Beilstein-Institut
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_ 1846082936142561280
score 13.22299

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