Efficient synthesis and free-radical scavenging capacity of new 2,4-substituted tetrahydroquinolines prepared via BiCl3-catalyzed three-component Povarov reaction, using N-vinylamides
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2011-09-25
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Abstract
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-methoxy1,2,3,4-tetrahydroquinolin-4-yl] acetamide 21 was ca. 2.2- fold more potent than the well-known antioxidant, vitamin E
(α-tocopherol).
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