Publication details
Novel Route to 4-(Adamantan-1-yl)quinoline Derivatives Based on the Friedlander Condensation
| Authors | |
|---|---|
| Year of publication | 2012 |
| Type | Article in Periodical |
| Magazine / Source | Helvetica Chimica Acta |
| MU Faculty or unit | |
| Citation | |
| Web | Full Text |
| Doi | http://dx.doi.org/10.1002/hlca.201100432 |
| Keywords | Friedlander condensation; Quinolines; adamantan-1-yl-; X-Ray crystallography |
| Description | 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 a-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 NMR spectroscopy and mass spectrometry. The molecular structures of five new quinolines, obtained via single-crystal X-ray diffraction analyses, are discussed. |