No abstract

2,3,4-Trisubstituted quinolines, substituted with adamantan-1-yl or (adamantan-1-yl)methyl in the 4position, were prepared from the corresponding admantan-1-yl 2-aminophenyl ketones or admantan-1ylmethyl 2-aminophenyl ketones and ketones with an a-CH 2 group. These reactions were carried out under neat conditions or in toluene, and the products were obtained in moderate-to-excellent yields. The scope and limitations of the examined procedures are discussed. All new compounds are fully characterized by IR and NMR spectroscopy and mass spectrometry. The molecular structures of five new quinolines, obtained via single-crystal X-ray diffraction analyses, are discussed.

Key indicators: single-crystal X-ray study; T = 120 K; mean (C-C) = 0.002 Å; R factor = 0.034; wR factor = 0.099; data-to-parameter ratio = 12.9.In the molecule of the title compound, C 25 H 24 FN, the dihedral angle between the best planes of the quinoline fragment (rings A and B) and the benzene ring (C) is 9.51 (4) . In the crystal, molecules are linked into centrosymmetric dimers via pairs of weak C-HÁ Á ÁF interactions. The molecules are stacked into chains along the a axis by weak off-set -interactions between the A and C rings of translation-related molecules with a centroid-centroid distance of 3.6440 (2) Å . Related literature

The asymmetric unit of the title compound, C18H23NO2, consists of two crystallographically independent mol­ecules bearing an adamantane cage consisting of three fused cyclo­hexane rings in almost ideal chair conformations, with C—C—C angles in the range 108.47 (16)–110.59 (15)°. Both aryl rings are essentially planar, the maximum deviation from the best plane being 0.0125 (19) Å. One conformer forms chains parallel to the b axis via N—H⋯O hydrogen bonds, whereas the second exhibits only an intra­molecular N—H⋯O hydrogen bond. The crystal structure is stabilized by further weak N—H⋯O and N—H⋯N inter­actions.

In the crystal of the title compound, C14H17NO2, mol­ecules are arranged into chains along the b axis linked via O—H⋯O hydrogen bonds. While the benzene ring is essentially planar, with a maximum deviation from the best plane of 0.003 (1) Å, the pyridine ring is slightly V-shaped: the distance of the carbonyl C atom from the benzene best plane is 0.120 (1) Å. The hy­droxy group is inclined markedly towards the benzene ring reducing the C—C—O bond angle to 113.21 (10)°.