Synthesis and spectroscopic and structural characterization of three new 2-methyl-4-styrylquinolines formed using Friedlander reactions between (2-aminophenyl)chalcones and acetone
Abstract
Three new 2-methyl-4-styrylquinoline derivatives have been synthesized in high yields using Friedländer reactions between chalcones [1-(2-aminophenyl)-3-arylprop-2-en-1-ones] and acetone, and characterized using IR, 1H and 13C NMR spectroscopy, and mass spectrometry, and by crystal structure analysis. In (E)-4-(4-fluorostyryl)-2-methylquinoline, C18H14FN, (I), the molecules are joined into cyclic centrosymmetric dimers by C—H⋯N hydrogen bonds and these dimers are linked into sheets by π–π stacking interactions. The molecules of (E)-2-methyl-4-[4-(trifluoromethyl)styryl]quinoline, C19H14F3N, (II), are linked into cyclic centrosymmetric dimers by C—H⋯π hydrogen bonds and these dimers are linked into chains by a single π–π stacking interaction. There are no significant hydrogen bonds in the structure of (E)-4-(2,6-dichlorostyryl)-2-methylquinoline, C18H13Cl2N, (III), but molecules related by translation along [010] form stacks with an intermolecular spacing of only 3.8628 (2) Å. Comparisons are made with the structures of some related compounds.
Citation
Rocío Vera , D , Mantilla , J P , Palma , A , Cobo , J & Glidewell , C 2022 , ' Synthesis and spectroscopic and structural characterization of three new 2-methyl-4-styrylquinolines formed using Friedlander reactions between (2-aminophenyl)chalcones and acetone ' , Acta Crystallographica Section C Structural Chemistry , vol. 78 , no. 10 , pp. 524-530 . https://doi.org/10.1107/S2053229622008634
Publication
Acta Crystallographica Section C Structural Chemistry
Status
Peer reviewed
ISSN
2053-2296Type
Journal article
Rights
Copyright © 2022 The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Description
Funding for this research was provided by: Vicerrectoría de Investigación y Extensión of the Industrial University of Santander (grant No. 2680 to AP); Universidad de Jaén and the Consejería de Economía, Innovación, Ciencia y Empleo (Junta de Andalucá, Spain) (award to JC).Collections
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