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4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones : crystal structures and regiochemistry

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Date
01/09/2020
Author
Rodríguez, Diego
Guerrero, Sergio Andrés
Palma, Alirio
Cobo, Justo
Glidewell, Christopher
Keywords
Synthesis
Cyclocondensation
Quinolone
Crystal structure
Molecular conformation
Hydrogen bonding
Supramolecular assembly
Regiochemistry
QD Chemistry
DAS
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Abstract
Structures are reported for two matched sets of substituted 4-styryl­quino­lines which were prepared by the formation of the heterocyclic ring in cyclo­condensation reactions between 1-(2-amino­phen­yl)-3-aryl­prop-2-en-1-ones with 1,3-dicarbonyl com­pounds. (E)-3-Acetyl-4-[2-(4-meth­oxy­phen­yl)ethen­yl]-2-methyl­quino­line, C21H19NO2, (I), (E)-3-acetyl-4-[2-(4-bromo­phen­yl)ethen­yl]-2-methyl­quino­line, C20H16BrNO, (II), and (E)-3-acetyl-2-methyl-4-{2-[4-(tri­fluoro­meth­yl)phen­yl]ethen­yl}quino­line, C21H16F3NO, (III), are isomorphous and in each structure the mol­ecules are linked by a single C—H...O hydrogen bond to form C(6) chains. In (I), but not in (II) or (III), this is augmented by a C—H...π(arene) hydrogen bond to form a chain of rings; hence, (I)–(III) are not strictly isostructural. By contrast with (I)–(III), no two of ethyl (E)-4-[2-(4-meth­oxy­phen­yl)ethen­yl]-2-methyl­quino­line-3-carboxyl­ate, C22H21NO3, (IV), ethyl (E)-4-[2-(4-bromo­phen­yl)ethen­yl]-2-methyl­quino­line-3-carboxyl­ate, C21H18BrNO2, (V), and ethyl (E)-2-methyl-4-{2-[4-(tri­fluoro­meth­yl)phen­yl]ethen­yl}quino­line-3-carboxyl­ate, C22H18F3NO2, (VI), are isomorphous. The mol­ecules of (IV) are linked by a single C—H...O hydrogen bond to form C(13) chains, but cyclic centrosymmetric dimers are formed in both (V) and (VI). The dimer in (V) contains a C—H...π(pyrid­yl) hydrogen bond, while that in (VI) contains two independent C—H...O hydrogen bonds. Comparisons are made with some related structures, and both the regiochemistry and the mechanism of the heterocyclic ring formation are discussed.
Citation
Rodríguez , D , Guerrero , S A , Palma , A , Cobo , J & Glidewell , C 2020 , ' 4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones : crystal structures and regiochemistry ' , Acta Crystallographica Section C Structural Chemistry , vol. 76 , no. 9 . https://doi.org/10.1107/S2053229620010803
Publication
Acta Crystallographica Section C Structural Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1107/S2053229620010803
ISSN
2053-2296
Type
Journal article
Rights
Copyright © 2020 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 de la Universidad Industrial de Santander (proyecto No. 2497, to AP); Universidad de Jaén, the Consejería de Economía, Innovación, Ciencia y Empleo (Junta de Andalucía, Spain) and Centro de Instrumentación Científico–Técnica of the Universidad de Jaén (UJA) (to JC).
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/20460

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