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Conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines: synthesis, and spectroscopic and structural characterization of five examples
Four new 2,4-distyrylquinolines and one 2-styryl-4-[2-(thiophen-2-yl)vinyl]quinoline have been synthesized using indium trichloride condensation reactions between aromatic aldehydes and the corresponding 2-methylquinolines, which were themselves prepared using Friedländer annulation reactions...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9985948/ https://www.ncbi.nlm.nih.gov/pubmed/36871291 http://dx.doi.org/10.1107/S2053229623001432 |
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author | Vera, Diana R. Ardila, Diana M. Palma, Alirio Cobo, Justo Glidewell, Christopher |
author_facet | Vera, Diana R. Ardila, Diana M. Palma, Alirio Cobo, Justo Glidewell, Christopher |
author_sort | Vera, Diana R. |
collection | PubMed |
description | Four new 2,4-distyrylquinolines and one 2-styryl-4-[2-(thiophen-2-yl)vinyl]quinoline have been synthesized using indium trichloride condensation reactions between aromatic aldehydes and the corresponding 2-methylquinolines, which were themselves prepared using Friedländer annulation reactions between mono- or diketones and (2-aminophenyl)chalcones: the products have all been fully characterized by spectroscopic and crystallographic methods. 2,4-Bis[(E)-styryl]quinoline, C(25)H(19)N, (IIa), and its dichloro analogue, 2-[(E)-2,4-dichlorostyryl]-4-[(E)-styryl]quinoline, C(25)H(17)Cl(2)N, (IIb), exhibit different orientations of the 2-styryl unit relative to the quinoline nucleus. In each of the 3-benzoyl analogues {2-[(E)-4-bromostyryl]-4-[(E)-styryl]quinolin-3-yl}(phenyl)methanone, C(32)H(22)BrNO, (IIc), {2-[(E)-4-bromostyryl]-4-[(E)-4-chlorostyryl]quinolin-3-yl}(phenyl)methanone, C(32)H(21)BrClNO, (IId), and {2-[(E)-4-bromostyryl]-4-[(E)-2-(thiophen-2-yl)vinyl]quinolin-3-yl}(phenyl)methanone, C(30)H(20)BrNOS, (IIe), the orientation of the 2-styryl unit is similar to that in (IIa), but the orientation of the 4-arylvinyl units show considerable variation. The thiophene unit in (IIe) is disordered over two sets of atomic sites having occupancies of 0.926 (3) and 0.074 (3). There are no hydrogen bonds of any kind in the structure of (IIa), but in (IId), a single C—H⋯O hydrogen bond links the molecules into cyclic centrosymmetric R (2) (2)(20) dimers. A combination of C—H⋯N and C—H⋯π hydrogen bonds links the molecules of (IIb) into a three-dimensional framework structure. A combination of three C—H⋯π hydrogen bonds links the molecules of (IIc) into sheets, and a combination of C—H⋯O and C—H⋯π hydrogen bonds forms sheets in (IIe). Comparisons are made with the structures of some related compounds. |
format | Online Article Text |
id | pubmed-9985948 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-99859482023-03-06 Conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines: synthesis, and spectroscopic and structural characterization of five examples Vera, Diana R. Ardila, Diana M. Palma, Alirio Cobo, Justo Glidewell, Christopher Acta Crystallogr C Struct Chem Research Papers Four new 2,4-distyrylquinolines and one 2-styryl-4-[2-(thiophen-2-yl)vinyl]quinoline have been synthesized using indium trichloride condensation reactions between aromatic aldehydes and the corresponding 2-methylquinolines, which were themselves prepared using Friedländer annulation reactions between mono- or diketones and (2-aminophenyl)chalcones: the products have all been fully characterized by spectroscopic and crystallographic methods. 2,4-Bis[(E)-styryl]quinoline, C(25)H(19)N, (IIa), and its dichloro analogue, 2-[(E)-2,4-dichlorostyryl]-4-[(E)-styryl]quinoline, C(25)H(17)Cl(2)N, (IIb), exhibit different orientations of the 2-styryl unit relative to the quinoline nucleus. In each of the 3-benzoyl analogues {2-[(E)-4-bromostyryl]-4-[(E)-styryl]quinolin-3-yl}(phenyl)methanone, C(32)H(22)BrNO, (IIc), {2-[(E)-4-bromostyryl]-4-[(E)-4-chlorostyryl]quinolin-3-yl}(phenyl)methanone, C(32)H(21)BrClNO, (IId), and {2-[(E)-4-bromostyryl]-4-[(E)-2-(thiophen-2-yl)vinyl]quinolin-3-yl}(phenyl)methanone, C(30)H(20)BrNOS, (IIe), the orientation of the 2-styryl unit is similar to that in (IIa), but the orientation of the 4-arylvinyl units show considerable variation. The thiophene unit in (IIe) is disordered over two sets of atomic sites having occupancies of 0.926 (3) and 0.074 (3). There are no hydrogen bonds of any kind in the structure of (IIa), but in (IId), a single C—H⋯O hydrogen bond links the molecules into cyclic centrosymmetric R (2) (2)(20) dimers. A combination of C—H⋯N and C—H⋯π hydrogen bonds links the molecules of (IIb) into a three-dimensional framework structure. A combination of three C—H⋯π hydrogen bonds links the molecules of (IIc) into sheets, and a combination of C—H⋯O and C—H⋯π hydrogen bonds forms sheets in (IIe). Comparisons are made with the structures of some related compounds. International Union of Crystallography 2023-02-22 /pmc/articles/PMC9985948/ /pubmed/36871291 http://dx.doi.org/10.1107/S2053229623001432 Text en © Vera et al. 2023 https://creativecommons.org/licenses/by/4.0/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. |
spellingShingle | Research Papers Vera, Diana R. Ardila, Diana M. Palma, Alirio Cobo, Justo Glidewell, Christopher Conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines: synthesis, and spectroscopic and structural characterization of five examples |
title | Conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines: synthesis, and spectroscopic and structural characterization of five examples |
title_full | Conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines: synthesis, and spectroscopic and structural characterization of five examples |
title_fullStr | Conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines: synthesis, and spectroscopic and structural characterization of five examples |
title_full_unstemmed | Conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines: synthesis, and spectroscopic and structural characterization of five examples |
title_short | Conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines: synthesis, and spectroscopic and structural characterization of five examples |
title_sort | conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines: synthesis, and spectroscopic and structural characterization of five examples |
topic | Research Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9985948/ https://www.ncbi.nlm.nih.gov/pubmed/36871291 http://dx.doi.org/10.1107/S2053229623001432 |
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