4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and regiochemistry.

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

SUBMITTER: Rodriguez D 

PROVIDER: S-EPMC7474186 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature