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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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dc.contributor.author | Rodríguez, Diego | |
dc.contributor.author | Guerrero, Sergio Andrés | |
dc.contributor.author | Palma, Alirio | |
dc.contributor.author | Cobo, Justo | |
dc.contributor.author | Glidewell, Christopher | |
dc.date.accessioned | 2020-08-13T12:30:02Z | |
dc.date.available | 2020-08-13T12:30:02Z | |
dc.date.issued | 2020-09-01 | |
dc.identifier.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 | en |
dc.identifier.issn | 2053-2296 | |
dc.identifier.other | PURE: 269528056 | |
dc.identifier.other | PURE UUID: 30437bc8-ef3f-4caf-a140-421090e1651c | |
dc.identifier.other | Scopus: 85090508498 | |
dc.identifier.other | WOS: 000581051900007 | |
dc.identifier.uri | https://hdl.handle.net/10023/20460 | |
dc.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). | en |
dc.description.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. | |
dc.format.extent | 8 | |
dc.language.iso | eng | |
dc.relation.ispartof | Acta Crystallographica Section C Structural Chemistry | en |
dc.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. | en |
dc.subject | Synthesis | en |
dc.subject | Cyclocondensation | en |
dc.subject | Quinolone | en |
dc.subject | Crystal structure | en |
dc.subject | Molecular conformation | en |
dc.subject | Hydrogen bonding | en |
dc.subject | Supramolecular assembly | en |
dc.subject | Regiochemistry | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | 4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones : crystal structures and regiochemistry | en |
dc.type | Journal article | en |
dc.description.version | Publisher PDF | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | https://doi.org/10.1107/S2053229620010803 | |
dc.description.status | Peer reviewed | en |
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