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 4-position, were prepared from the corresponding admantan-1-yl 2-aminophenyl ketones or admantan-1-ylmethyl 2-aminophenyl ketones and ketones with an α-CH2 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 NMRspectroscopy and mass spectrometry. The molecular structures of five new quinolines, obtained via single-crystal X-ray diffraction analyses, are discussed. © 2012 Verlag Helvetica Chimica Acta AG.