title: Efficient synthesis and free-radical scavenging capacity of new 2,4-substituted tetrahydroquinolines prepared via BiCl₃-catalyzed three-component Povarov reaction, using N-vinylamides.
abstract: Efficient synthesis of new structurally different 2-(het)aryl-4-amidyl-substituted tetrahydroquinolines 8-29 is reported. The synthesis based on BiCl(3)-catalyzed three-component Povarov reaction between anilines, (het)aryl aldehydes and enamides offers a fast, safe, and cheap way for efficient tetrahydroquinoline libraries construction. Using N-vinylamides (N-vinylpyrrolidin-2-one and N-vinylacetamide) in this reaction, it was possible to obtain two series of different cis tetrahydroquinolines with antioxidant properties. Among 14 tested compounds, 7 tetrahydroquinolines revealed a prominent anti-radical capacity, equal or higher than that of the commercial antioxidants. Being the most active molecule, the N-[2-(α-furanyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-4-yl] acetamide 21 was ca. 2.2-fold more potent than the well-known antioxidant, vitamin E (α-tocopherol).
authors.affiliation: Laboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad Industrial de Santander, AA 678, Bucaramanga, Colombia. kouznet@uis.edu.co
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Kouznetsov
authors.forename: Carlos M Meléndez
authors.initials: CM
authors.lastname: Gómez
authors.forename: Luz K Luna
authors.initials: LK
authors.lastname: Parada
authors.forename: John H
authors.initials: JH
authors.lastname: Bermudez
authors.forename: Leonor Y Vargas
authors.initials: LY
authors.lastname: Méndez
authors.forename: Amner Muñoz
authors.initials: AM
authors.lastname: Acevedo
mesh_terms: D000577:Amides / Q000737:chemistry*; D001729:Bismuth / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D002712:Chlorides / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000577:Amides; D002712:Chlorides; D016166:Free Radical Scavengers; D011804:Quinolines; C534543:bismuth trichloride; C542964:1,2,3,4-tetrahydroquinoline; D001729:Bismuth