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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dc.contributor.authorKouznetsov, Vladimir V.
dc.contributor.authorMeléndez Gómez, Carlos M.
dc.contributor.authorLuna Parada, Luz K.
dc.contributor.authorBermudez, John H.
dc.contributor.authorVargas Méndez, Leonor Y.
dc.contributor.authorMuñoz Acevedo, Amner
dc.date.accessioned2020-02-18T14:43:55Z
dc.date.available2020-02-18T14:43:55Z
dc.date.issued2011-09-25
dc.description.abstractEfficient 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).spa
dc.description.domainhttp://unidadinvestigacion.usta.edu.cospa
dc.format.mimetypeapplication/pdf
dc.identifier.doihttps://doi.org/10.1007/s11030-011-9330-5spa
dc.identifier.urihttp://hdl.handle.net/11634/21762
dc.publisher.branchCRAI-USTA Bogotáspa
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dc.rightsAtribución-NoComercial-CompartirIgual 2.5 Colombia
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/2.5/co/
dc.subject.keywordMCRsspa
dc.subject.keywordReaction imino Diels–Alder (Povarov)spa
dc.subject.keyword2,4-disubstituted tetrahydroquinolinesspa
dc.subject.keywordStructural diversityspa
dc.subject.keywordDOS methodologyspa
dc.subject.keywordAntioxidant agentsspa
dc.titleEfficient synthesis and free-radical scavenging capacity of new 2,4-substituted tetrahydroquinolines prepared via BiCl3-catalyzed three-component Povarov reaction, using N-vinylamidesspa
dc.type.categoryGeneración de Nuevo Conocimiento: Artículos publicados en revistas especializadas - Electrónicosspa

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