Molecular structures and crystal packings of 2-styrylquinoline and its derivatives

Synthesis and spectroscopic and structural characterization of three new 2-methyl-4-styrylquinolines formed using Friedländer reactions between (2-aminophenyl)chalcones and acetone

“…This may reflect, at least in part, a lack of efficient, straightforward and versatile routes to other isomeric styrylquinolines. The structure of 2-styrylquinoline itself has been reported three times (Valle et al, 1986;Gulakova et al, 2011;Kuz'mina et al, 2011), as have those of 2-[2-(4-methylphenyl)vinyl]quinoline Kuz'mina et al, 2011;Das et al, 2019) and 2-[2-(3,4methoxyphenyl)vinyl]quinolone (Gulakova et al, 2011;Kuz'mina et al, 2011;Sharma et al, 2021). There are two reports on the structure of 2-[2-(3-nitrophenyl)vinyl]quinoline (Gulakova et al, 2011;Kuz'mina et al, 2011) and one on the structure of 4-phenyl-2-styrylquinoline (Makela et al, 2021).…”

“…The structure of 2-styrylquinoline itself has been reported three times (Valle et al, 1986;Gulakova et al, 2011;Kuz'mina et al, 2011), as have those of 2-[2-(4-methylphenyl)vinyl]quinoline Kuz'mina et al, 2011;Das et al, 2019) and 2-[2-(3,4methoxyphenyl)vinyl]quinolone (Gulakova et al, 2011;Kuz'mina et al, 2011;Sharma et al, 2021). There are two reports on the structure of 2-[2-(3-nitrophenyl)vinyl]quinoline (Gulakova et al, 2011;Kuz'mina et al, 2011) and one on the structure of 4-phenyl-2-styrylquinoline (Makela et al, 2021). In all of these 2-styrylquinolines, the molecular skeleton is planar, in marked contrast to the nonplanar conformations of the 4-styrylquinoline derivatives (I)-(III) reported here, and of those reported previously (Rodrı ´guez et al, 2020).…”

Molecular structures and crystal packings of 2-styrylquinoxaline derivatives

“…Within this process, the ethylene fragment of the С-СН=СН-С system rotates around the single C-C bonds, whereas aromatic substituents undergo only slight shifts in their planes. The bicycle pedal dis ordering has been observed many times before in the crystal structures of neutral styrylheterocycles Ar-CH=CH-Het and their corresponding dyes [Ar-CH=CH-Het] + X -(where Het is a nitrogen contain ing heterocycle and X -is a counterion) [5][6][7][8][9]. In the 2 styrylquinoxaline derivatives 1-4, the pla narity of molecules is maintained to different extent.…”

“…In the 2 styrylquinoxaline derivatives 1-4, the pla narity of molecules is maintained to different extent. The dihedral angles between the planes of the ethylene fragment С1-С2=С3-С4 and the benzene ring, between the planes of the ethylene fragment and the six membered N containing heterocycle, and between the planes of the benzene ring and the hetero cycle, respectively, are as follows These data indicate that the ethylene bond is localized to a large extent, as is generally character istic of styrylheterocycles and corresponding dyes [1,[3][4][5][6][7][8][9]. On the whole, this facilitates the implementa tion of the PCA reaction in ethylene compounds, since it is known that as the conjugation is strength ened, the ability of these systems to enter into the PCA reaction decreases [1,[4][5][6][7].…”

“…This work continues our studies of molecular and crystal structures of styrylheterocycles and corre sponding styryl dyes [1][2][3][4][5][6][7][8][9]. These compounds of the general formulas Het-CH=CH-Ar and [Het + -CH=CH-Ar]X -(where Het is a nitrogen containing heterocycle and X -is a counterion), respectively, are able to enter into the reaction of [2 + 2] photocycload dition (PCA) under irradiation with light of the visible or near UV region.…”