caa a22 4500 44587886X CHVBK 20180317145536.0 cr unu---uuuuu 170323e20111101xx s 000 0 eng 10.1007/s11030-011-9330-5 doi (NATIONALLICENCE)springer-10.1007/s11030-011-9330-5 Efficient synthesis and free-radical scavenging capacity of new 2,4-substituted tetrahydroquinolines prepared via BiCl3-catalyzed three-component Povarov reaction, using N -vinylamides [Elektronische Daten] [Vladimir Kouznetsov, Carlos Gómez, Luz Parada, John Bermudez, Leonor Méndez, Amner Acevedo] Efficient synthesis of new structurally different 2-(het)aryl-4-amidyl-substituted tetrahydroquinolines 8-29 is reported. The synthesis based on BiCl3-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). Springer Science+Business Media B.V., 2011 MCRs nationallicence Reaction imino Diels-Alder (Povarov) nationallicence 2,4-disubstituted tetrahydroquinolines nationallicence Structural diversity nationallicence DOS methodology nationallicence Antioxidant agents nationallicence Kouznetsov Vladimir Laboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia aut Gómez Carlos Grupo de Investigación en Compuestos Heterocíclicos, Programa de Química, Facultad de Ciencias Básicas, Universidad del Atlántico, A.A. 1890, Barranquilla, Colombia aut Parada Luz Laboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia aut Bermudez John Laboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia aut Méndez Leonor Grupo de Investigaciones Ambientales, Facultad de Química Ambiental, Universidad Santo Tomás, A.A. 1076, Bucaramanga, Colombia aut Acevedo Amner Departamento de Química y Biología, Universidad del Norte, A.A. 1569, Barranquilla, Colombia aut Molecular Diversity Springer Netherlands 15/4(2011-11-01), 1007-1016 1381-1991 15:4<1007 2011 15 11030 https://doi.org/10.1007/s11030-011-9330-5 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s11030-011-9330-5 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Kouznetsov Vladimir Laboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia aut NATIONALLICENCE 700 1- Gómez Carlos Grupo de Investigación en Compuestos Heterocíclicos, Programa de Química, Facultad de Ciencias Básicas, Universidad del Atlántico, A.A. 1890, Barranquilla, Colombia aut NATIONALLICENCE 700 1- Parada Luz Laboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia aut NATIONALLICENCE 700 1- Bermudez John Laboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia aut NATIONALLICENCE 700 1- Méndez Leonor Grupo de Investigaciones Ambientales, Facultad de Química Ambiental, Universidad Santo Tomás, A.A. 1076, Bucaramanga, Colombia aut NATIONALLICENCE 700 1- Acevedo Amner Departamento de Química y Biología, Universidad del Norte, A.A. 1569, Barranquilla, Colombia aut NATIONALLICENCE 773 0- Molecular Diversity Springer Netherlands 15/4(2011-11-01), 1007-1016 1381-1991 15:4<1007 2011 15 11030 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer