Conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines : synthesis, and spectroscopic and structural characterization of five examples
Abstract
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, C25H19N, (IIa), and its dichloro analogue, 2-[(E)-2,4-dichlorostyryl]-4-[(E)-styryl]quinoline, C25H17Cl2N, (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, C32H22BrNO, (IIc), {2-[(E)-4-bromostyryl]-4-[(E)-4-chlorostyryl]quinolin-3-yl}(phenyl)methanone, C32H21BrClNO, (IId), and {2-[(E)-4-bromostyryl]-4-[(E)-2-(thiophen-2-yl)vinyl]quinolin-3-yl}(phenyl)methanone, C30H20BrNOS, (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 R22(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.
Citation
Vera , D R , Ardila , D M , Palma , A , Cobo , J & Glidewell , C 2023 , ' Conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines : synthesis, and spectroscopic and structural characterization of five examples ' , Acta Crystallographica Section C Structural Chemistry , vol. 79 , no. Part 3 , C79 , pp. 94-103 . https://doi.org/10.1107/s2053229623001432
Publication
Acta Crystallographica Section C Structural Chemistry
Status
Peer reviewed
ISSN
2053-2296Type
Journal article
Description
Funding for this research was provided by: Vicerrectoría de Investigación y Extensión of the Industrial University of Santander (grant No. 2680).Collections
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