Novel Route to 4‐(Adamantan‐1‐yl)quinoline Derivatives Based on the Friedländer Condensation

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.

4-(Adamantan-1-yl)-2-(4-fluorophenyl)quinoline

“…62 (19) and 66.77 (15)°, respectively. Although the quinoline ring is essentially planar, it is markedly deformed in plane as it is usual for similar quinoline rings substituted with bulky adamantane at position 4 (Kozubková et al, 2012). The most affected valence angles N1-C9-C8, C2-C3-C4, N1-C9-C4 and C3-C4-C5 are 115.82 (11), 115.91 (11), 124.06 12and 125.91 (12)°, respectively.…”

“…For the preparation and spectroscopic properties of the title compound, see: Kozubková et al (2012). For related structures, see: Kozubková et al (2012); Prabhuswamy et al (2012). For the biological activity of related compounds, see: Nayyar et al (2009).…”

“…As an example, derivatives of 4-(1-adamantyl)quinoline-2-carboxylic acid have been recently described as potent antituberculosis agents (Nayyar et al, 2009). The title compound was prepared as a part of our research aimed at the examination of novel convenient synthetic procedures toward 4-(1adamantyl)quinoline derivatives (Kozubková et al, 2012).…”

“…The title compound was prepared via a Friedländer reaction from the corresponding 1-adamantyl aminophenyl ketone and 4-fluoroacetophenone as it has been described previously (Kozubková et al, 2012). A single-crystal usable for X-ray analysis was obtained by slow spontaneous evaporation from deuterochloloform at room temperature.…”