Rodríguez Diego, Guerrero Sergio Andrés, Palma Alirio, Cobo Justo, Glidewell Christopher
Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, AA 678, Bucaramanga, Colombia.
Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain.
Acta Crystallogr C Struct Chem. 2020 Sep 1;76(Pt 9):883-890. doi: 10.1107/S2053229620010803. Epub 2020 Aug 13.
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, CHNO, (I), (E)-3-acetyl-4-[2-(4-bromophenyl)ethenyl]-2-methylquinoline, CHBrNO, (II), and (E)-3-acetyl-2-methyl-4-{2-[4-(trifluoromethyl)phenyl]ethenyl}quinoline, CHFNO, (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, CHNO, (IV), ethyl (E)-4-[2-(4-bromophenyl)ethenyl]-2-methylquinoline-3-carboxylate, CHBrNO, (V), and ethyl (E)-2-methyl-4-{2-[4-(trifluoromethyl)phenyl]ethenyl}quinoline-3-carboxylate, CHFNO, (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.
报道了两组匹配的取代4-苯乙烯基喹啉的结构，它们是通过1-(2-氨基苯基)-3-芳基丙-2-烯-1-酮与1,3-二羰基化合物之间的环缩合反应形成杂环而制备的。(E)-3-乙酰基-4-[2-(4-甲氧基苯基)乙烯基]-2-甲基喹啉，CHNO，(I)，(E)-3-乙酰基-4-[2-(4-溴苯基)乙烯基]-2-甲基喹啉，CHBrNO，(II)，以及(E)-3-乙酰基-2-甲基-4-{2-[4-(三氟甲基)苯基]乙烯基}喹啉，CHFNO，(III)，是同构的，并且在每个结构中，分子通过单个C-H...O氢键相连形成C(6)链。在(I)中，但不在(II)或(III)中，这通过C-H...π(芳烃)氢键得到增强，形成环链；因此，(I)-(III)并非严格的同构结构。与(I)-(III)相反，(E)-4-[2-(4-甲氧基苯基)乙烯基]-2-甲基喹啉-3-羧酸乙酯，CHNO，(IV)、(E)-4-[2-(4-溴苯基)乙烯基]-2-甲基喹啉-3-羧酸乙酯，CHBrNO，(V)和(E)-2-甲基-4-{2-[4-(三氟甲基)苯基]乙烯基}喹啉-3-羧酸乙酯，CHFNO，(VI)中没有两个是同构的。(IV)的分子通过单个C-H...O氢键相连形成C(13)链，但(V)和(VI)中均形成了中心对称的环状二聚体。(V)中的二聚体包含一个C-H...π(吡啶基)氢键，而(VI)中的二聚体包含两个独立的C-H...O氢键。与一些相关结构进行了比较，并讨论了区域化学和杂环形成的机理。
