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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; Gutiérrez, Luisa F; Insuasty, Braulio; Quiroga, Jairo; Laali, Kenneth K; Zhao, Chunqing; Borosky, Gabriela L; Horwitz, Samantha M; Bunge, Scott D.
Afiliação
  • Abonia R; Research Group of Heterocyclic Compounds (GICH), Department of Chemistry, Universidad del Valle, A. A. 25360, Cali, Colombia.
  • Gutiérrez LF; Research Group of Heterocyclic Compounds (GICH), Department of Chemistry, Universidad del Valle, A. A. 25360, Cali, Colombia.
  • Insuasty B; Department of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, FL 32224, USA.
  • Quiroga J; Research Group of Heterocyclic Compounds (GICH), Department of Chemistry, Universidad del Valle, A. A. 25360, Cali, Colombia.
  • Laali KK; Research Group of Heterocyclic Compounds (GICH), Department of Chemistry, Universidad del Valle, A. A. 25360, Cali, Colombia.
  • Zhao C; Department of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, FL 32224, USA.
  • Borosky GL; Department of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, FL 32224, USA.
  • Horwitz SM; INFIQC, CONICET and Departamento de Química Teórica y Computacional, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba 5000, Argentina.
  • Bunge SD; Department of Chemistry and Biochemistry, Kent State University, Kent, OH 44242, USA.
Beilstein J Org Chem ; 15: 642-654, 2019.
Article em En | MEDLINE | ID: mdl-30931006
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.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Beilstein J Org Chem Ano de publicação: 2019 Tipo de documento: Article País de afiliação: Colômbia País de publicação: Alemanha
Texto completo
Adicionar na Minha BVS
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Beilstein J Org Chem Ano de publicação: 2019 Tipo de documento: Article País de afiliação: Colômbia País de publicação: Alemanha