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

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

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)...

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Main Authors: Rodrigo Abonia, Luisa F. Gutiérrez, Braulio Insuasty, Jairo Quiroga, Kenneth K. Laali, Chunqing Zhao, Gabriela L. Borosky, Samantha M. Horwitz, Scott D. Bunge
Format: Article
Language:English
Published: Beilstein-Institut 2019-03-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
model heteroarylmethylium salts
multicomponent
one-pot catalyst-free assembly
pharmacophoric triads
three-component synthesis
tris(heteroaryl)methanes
Yonemitsu-type reaction
Online Access:https://doi.org/10.3762/bjoc.15.60
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spelling doaj-a6521e86984a4951a085c1afd72f11d62021-02-02T04:31:22ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972019-03-0115164265410.3762/bjoc.15.601860-5397-15-60Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation saltsRodrigo Abonia0Luisa F. Gutiérrez1Braulio Insuasty2Jairo Quiroga3Kenneth K. Laali4Chunqing Zhao5Gabriela L. Borosky6Samantha M. Horwitz7Scott D. Bunge8Research Group of Heterocyclic Compounds (GICH), Department of Chemistry, Universidad del Valle, A. A. 25360, Cali, ColombiaResearch Group of Heterocyclic Compounds (GICH), Department of Chemistry, Universidad del Valle, A. A. 25360, Cali, ColombiaResearch Group of Heterocyclic Compounds (GICH), Department of Chemistry, Universidad del Valle, A. A. 25360, Cali, ColombiaResearch Group of Heterocyclic Compounds (GICH), Department of Chemistry, Universidad del Valle, A. A. 25360, Cali, ColombiaDepartment of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, FL 32224, USADepartment of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, FL 32224, USAINFIQC, CONICET and Departamento de Química Teórica y Computacional, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba 5000, ArgentinaDepartment of Chemistry and Biochemistry, Kent State University, Kent, OH 44242, USADepartment of Chemistry and Biochemistry, Kent State University, Kent, OH 44242, USAA 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.https://doi.org/10.3762/bjoc.15.60model heteroarylmethylium saltsmulticomponentone-pot catalyst-free assemblypharmacophoric triadsthree-component synthesistris(heteroaryl)methanesYonemitsu-type reaction
collection DOAJ
language English
format Article
sources DOAJ
author Rodrigo Abonia
Luisa F. Gutiérrez
Braulio Insuasty
Jairo Quiroga
Kenneth K. Laali
Chunqing Zhao
Gabriela L. Borosky
Samantha M. Horwitz
Scott D. Bunge
spellingShingle Rodrigo Abonia
Luisa F. Gutiérrez
Braulio Insuasty
Jairo Quiroga
Kenneth K. Laali
Chunqing Zhao
Gabriela L. Borosky
Samantha M. Horwitz
Scott D. Bunge
Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
Beilstein Journal of Organic Chemistry
model heteroarylmethylium salts
multicomponent
one-pot catalyst-free assembly
pharmacophoric triads
three-component synthesis
tris(heteroaryl)methanes
Yonemitsu-type reaction
author_facet Rodrigo Abonia
Luisa F. Gutiérrez
Braulio Insuasty
Jairo Quiroga
Kenneth K. Laali
Chunqing Zhao
Gabriela L. Borosky
Samantha M. Horwitz
Scott D. Bunge
author_sort Rodrigo Abonia
title Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
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
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2019-03-01
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.
topic model heteroarylmethylium salts
multicomponent
one-pot catalyst-free assembly
pharmacophoric triads
three-component synthesis
tris(heteroaryl)methanes
Yonemitsu-type reaction
url https://doi.org/10.3762/bjoc.15.60
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