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A three-step pathway from (2-amino­phenyl)chal­cones to novel styryl­quinoline–chalcone hybrids: synthesis and spectroscopic and structural characterization of three examples

Three new styryl­quinoline–chalcone hybrids have been synthesized using a three-step pathway starting with Friedländer cyclo­condensation between (2-amino­phen­yl)chalcones and acetone to give 2-methyl-4-styryl­quinolines, followed by selective oxidation to the 2-formyl analogues, and finally Claise...

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Detalles Bibliográficos
Autores principales: Vera, Diana R., Mantilla, Juan P., Palma, Alirio, Díaz Costa, Iván, Cobo, Justo, Glidewell, Christopher
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9813925/
https://www.ncbi.nlm.nih.gov/pubmed/36602015
http://dx.doi.org/10.1107/S2053229622011263
Descripción
Sumario:Three new styryl­quinoline–chalcone hybrids have been synthesized using a three-step pathway starting with Friedländer cyclo­condensation between (2-amino­phen­yl)chalcones and acetone to give 2-methyl-4-styryl­quinolines, followed by selective oxidation to the 2-formyl analogues, and finally Claisen–Schmidt condensation between the formyl inter­mediates and 1-acetyl­naph­tha­lene. All inter­mediates and the final products have been fully characterized by IR and (1)H/(13)C NMR spectroscopy, and by high-resolution mass spectrometry, and the three products have been characterized by single-crystal X-ray diffraction. The mol­ecular conformations of (E)-3-{4-[(E)-2-phenyl­ethen­yl]quinolin-2-yl}-1-(naph­tha­len-1-yl)prop-2-en-1-one, C(30)H(21)NO, (IVa), and (E)-3-{4-[(E)-2-(4-fluoro­phen­yl)ethen­yl]quinolin-2-yl}-1-(naph­tha­len-1-yl)prop-2-en-1-one, C(30)H(20)FNO, (IVb), are very similar. In each com­pound, the mol­ecules are linked into a three-dimensional array by hydro­gen bonds, of the C—H⋯O and C—H⋯N types in (IVa), and of the C—H⋯O and C—H⋯π types in (IVb), and by two independent π–π stacking inter­actions. By contrast, the conformation of the chalcone unit in (E)-3-{4-[(E)-2-(2-chloro­phen­yl)ethen­yl]quinolin-2-yl}-1-(naph­tha­len-1-yl)prop-2-en-1-one, C(30)H(20)ClNO, (IVc), differs from those in (IVa) and (IVb). There are only weak hydro­gen bonds in the structure of (IVc), but a single rather weak π–π stacking inter­action links the mol­ecules into chains. Comparisons are made with some related structures.